Index

* = Includes Audience Choice

CITY LIFE

Best of the Best: Andersonville (2002)
Best of the Best: Art Institute of Chicago (2002)
Best of the Best: Blommer Chocolate (2002)
Best of the Best: Boystown (2002)
Best of the Best: Chicago Federal Center (2002)
Best of the Best: Cicero (2002)
Best of the Best: The Daley machine (2002)
Best of the Best: Devon Avenue (2002)
Best of the Best: Grant Park (2002)
Best of the Best: Greektown (2002)
Best of the Best: Hilliard Homes and Marina City (2002)
Best of the Best: Holy Trinity Russian Orthodox Cathedral (2002)
Best of the Best: The intersection of Damen, North and Milwaukee (2002)
Best of the Best: John Hancock Center (2002)
Best of the Best: The Lakefront (2002)
Best of the Best: Lincoln Park (2002)
Best of the Best: Little Italy (2002)
Best of the Best: The Market District (2002)
Best of the Best: Navy Pier(2002)
Best of the Best: Parakeets in Hyde Park (2002)
Best of the Best: Pullman (2002)
Best of the Best: Sears Tower (2002)
Best of the Best: The Sun-Times’ writers (2002)
Best abiding sorrow mistaken for performance art (2007)
Best Abundant Instagram Subject (2018)
*Best accomplishment not yet carved on Burris’ tombstone (2009)
Best activist in the interest of the public defense (2015)
Best addition to the local green economy (2015)
*Best airport security story, post-9/11 (2002)
Best (and tastiest) way to support merchants who are struggling while the city builds a forward-thinking streetscape (2015)
Best Anti-Trump Protest (2017)
Best architectural patron in Chicago (2016)
Best architectural restoration (2007)
Best Argument Against the Myth of Chicago as a Second City, An Essay (2016)
Best argument for automated speed-enforcement cameras (2013)
Best attempt by a media organization to ignite social change (2014)
Best attempt to use sports as a platform for change (2016)
*Best baby name for the Pete Wentz-Ashlee Simpson offspring (2008)
Best of the Best: “The Adventures of Augie March” (2002)
Best bar to crash a truck into (2019)
*Best Barack Obama moment (2008)
Best beach just over the border (2016)
*Best bet about where Groupon’s stock price will be in 2017 (2012)
*Best bet to be the “next Oprah” from Chicago (2010)
*Best big Chicago company to work for (2008)
Best bike path for misanthropic cyclists (2015)
Best bilingual community radio station (2012)
Best birth justice organization (2019)
Best “Blues Brothers” location still in Chicago (2015)
Best Bridge in Chicago to Give the Finger to a Building (2018)
Best budding media mogul (2009)
Best building that is widely hated by the public (2016)
Best Building to Be in While It Rains (2018) 
*Best candidate for governor (2002)
*Best candidate for governor (2014)
*Best candidate for governor of Illinois (2009)
*Best candidate for mayor, whether declared or not (2014)
*Best candidate for mayor who is likely to run (2010)
*Best candidate for mayor who is unlikely to run (2010)
*Best candidate for president, regardless of whether he or she is from Chicago (2012)
*Best candidate for senator (2014)
Best car museum (2019)
Best caution against Wicker Park nightlife (circa 1985) (2019)
Best celebrity sighting at Soho House (2016)
Best celebrity sighting in the past year (2007)
Best cemetery (2015)
Best chance of making Time’s 100 Most Influential List in 2012 (2011)
Best Chicago-accent diatribe by someone in public office in the last year (2013)
Best Chicago-centric Internet spectacle (2016)
*Best Chicago holiday tradition (2010)
Best Chicago landmark, Leader of Culture (2015) 
Best Chicago landmark coming in 2016 (2015)
Best Chicago Structures That Tell Us What It Means to Be An American Right Now, An Essay (2016)
*Best Chicago Twitterer for news (2013)
*Best Chicago news columnist (other than Tony Fitzpatrick, of course) (2014)
Best choreographic homecoming, Leader of Culture (2015)
Best citizen debt relief under Mayor Lightfoot (to date) (2019)
Best citizen during the polar vortex (2019)
*Best city of Chicago department head (2013)
Best city of Chicago sustainability initiative that is suffering the most push back (2013)
Best city-sponsored energy-efficiency Initiative (2014)
Best city wildlife (2019)
Best classical theater, Leader of Culture (2015)
Best collective carrying the torch of the Black Panther Party (2019)
Best commercial Pinterest account (2012)
Best community engagement project through artistic intervention (2016)
Best community reinvestment (2016)
Best concentration of “ghost signs” (2016)
Best Conclusion To A Dark Chicago Timeline Among Dark American Timelines (2018)
Best cross-pollination of an Archie Bunker/Donald Trump love child (2016)
Best crosswalk update (2012)
Best CTA Blue Line mishap (2014)
Best CTA success story (2013)
Best dancing by a mayor of Chicago (2019)
Best Dark Clown in the Age of Trump (2017)
Best Dark Horse for Mayor (2018)
*Best dating nightmare (2002)
Best day trip to Bedford Falls (2010)
Best David beats Goliath moment (2015)
*Best Democratic candidate for US president (2007)
Best Demonstration of Rubbing Success in Yo’ Face (2017)
Best desperate attempt to land the 2016 Olympics (2008)
Best diabolically Trump-hating cat to follow on Twitter, Leader of Culture (2015)
Best Dream of Snow, As Recorded By Nelson Algren (2018) 
Best-dressed artist (2013)
Best developer-held land portfolio (2015)
Best Dive Bar Winterization (2018)
Best downtown spots for an office worker to smoke a joint at lunch, or so we’ve heard (2016)
Best El line for napping (2015) 
Best El ride for graffiti (2013)
*Best El station (2011)
*Best El station for an earache (2002)
Best El station to witness a free musical performance (2012)
Best election that never happened (2015)
Best European import (2008)
Best Evocation of Turn-of-the-Twentieth Century Wicker Park Spring from Jessica Hopper’s “Night Moves” (2018) 
Best Evocation of Turn-of-the-Twentieth Century Wicker Park Summer from Jessica Hopper’s “Night Moves” (2018)
Best Evocation of Turn-of-the-Twentieth Century Wicker Park Winter from Jessica Hopper’s “Night Moves” (2018)
*Best example of a memo that Tribune executives Lee Abrams or Randy Michaels might write, but haven’t (2008)
Best Example of Chicago Media Stumbling into the “Who, Me?” Era (2018)
Best example of Chicago’s global footprint (2012)
Best example of fighting the man and winning (2011)
Best example of former mayor Richard M. Daley channeling Gertrude Stein (2013)
Best example of how Chicago continues to neglect its great blues heritage (2015)
Best example of ruining a neighborhood while giving it life at the same time (2016)
Best example of the failing of local television, Leader of Culture (2015)
Best example of why some folks are oblivious to the real estate crash and financial meltdown (2008)
Best execution of media activism (2014)
Best existential annoyance on the CTA (2019)
Best Facebook Neighborhood Group (2017)
Best free outdoor activity, Leader of Culture (2015)
Best fresh description of the Chicago Fire (2019)
Best funeral procession (2014)
Best fusion of passion and commerce (2009)
Best future candidate for president, regardless of whether he or she is from Chicago (2012)
*Best future owner of the Chicago Tribune (2011)
Best G-Rated Thing to Do While Lying on Your Back (2017)
Best global foresight (2012)
Best government-watchdog agency striving to keep Illinois free from financial folly (2016)
*Best guess about why the CTA decided to implement the new Ventra card system (2013)
*Best guess as to which project gets done first: Redevelopment of US Steel Southworks site on south lakefront; construction of the Chicago Spire; redevelopment of Old Chicago Main Post Office or CTA Red Line extension to 130th Street (2014)
*Best haunted site (2013)
Best Haunted Spot Not Yet Discovered (2017)
Best hidden park (2010)
Best historic fever dream from a 1928 Chicago rooming house (2019)
Best historic punch-drunk description of late-1960s Chicago gambling (2019)
Best historic shrieking about Chicago “bohemia” (2019)
Best Hold-All Title for a Rahm Emanuel Book (2018) 
*Best hotel lobby (2010)
*Best iconic Chicago personality now that Studs is gone (2009)
Best iconic landmark you could buy, Leader of Culture (2015) 
Best iconic transformation (2008)
*Best idea for the next civic spectacle, after this year’s Great Chicago Fire Festival triumph (2014)
*Best idea to fix the CTA (2007)
*Best idea to forget about from Chicago 2016 (2009)
*Best idea to salvage from Chicago 2016 (2009)
Best idea we’d like to really see catch fire (2008)
*Best imaginary Oprah moment that won’t likely actually happen but, well, might have (2010)
*Best imaginary Oprah moment that won’t likely actually happen but, well, no, it never would (2010)
*Best imaginary Sun-Times headline (2002)
*Best imaginary Twitter post by Patti Blagojevich (2009)
*Best imagined dialogue between Sun-Times editor Jim Kirk and Michael Ferro, parent company Wrapports chairman, in deciding to eliminate the entire photography staff (2013)
Best immobile street performer (2013)
Best impersonation of a true Chicago politician (2011)
Best implement for calling dibs (2015) 
Best indicator that America needs a new healthcare policy (2009)
Best indicator(s) that America still needs a new healthcare policy (2012)
Best indoor make-out spot (2010)
Best Initiative Shown By Dogged Chicago Journalists (2018)
Best international trip within Chicago, Leader of Culture (2015) 
Best internet station to soon hit the radio dial (2014)
Best Intimation of Mortality that Quickly Becomes Incessant Music (2018)
Best Investigative Journalism Debut (2017)
Best investigative reporting on Chicago crime (2015)
Best Kickstarter campaign (2012)
Best live Twitter feed of roadwork, Leader of Culture (2015)
Best Local Battle for Territory (2017)
*Best local daily newspaper  (2014)
Best local digital controversy (2007)
Best local drug scare (2013)
Best Local Enterprise Reporting To Survive Post-Gawker Jitters (2017)
*Best local general-interest blog (2009)
*Best local general-interest blog (2014)
Best local Instagram (2015)
Best local internet muckraker (2012)
Best local media trend (2016)
*Best local nonprofit (2007)
*Best local podcast (2010)
Best Local, Radically Politicized Live News Show (2017)
*Best local radio station (2011)
*Best local transit app (2013)
*Best local TV weatherman (2011)
Best local window on the world (2012)
Best location for the Obama Presidential Library (2014)
Best longtime local web magazine to go on hiatus (2016)
*Best-looking female local TV personality (2011)
*Best-looking male local TV personality (2011)
Best loving relationship between a panhandler and a dog (2016)
Best macrocosmic El stop (2010)
Best makeout spot (2015)
Best mascot (2015)
*Best mayoral campaign slogan for Rahm (2010)
*Best Mayor Daley accomplishment of the past year (2009)
*Best Mayor Emanuel accomplishment of the past year (2014)
*Best Mayor Emanuel debacle of the past year (2014)
Best Mayor Daley debacle of the past year (2009)
Best memorial to heroic animals and circus performers (2013)
*Best memory from the trial of Rod Blagojevich (2010)
Best missed but little-known local figure (2008)
Best mid-century modern thoroughfare you never stop on (2015)
Best moment that made us proud of our country (2008)
Best museum award that probably won’t make the corporate stationery (2011)
Best Museum to Take Kids If You Want to Stress Out the Guards (2018) 
Best Museum to Take Kids That’s Not The Chicago Children’s Museum (2018)
*Best name for the building formerly known as Sears Tower (2009)
*Best name for The 606, other than The 606 or the Bloomingdale Trail (2013)
Best Neighborhood Block Party (2017)
*Best neighborhood in which to weather the possible decline in real estate values precipitated, among other things, by the mortgage crisis (2007)
*Best neighborhood in which to exploit the possible decline in real estate values precipitated, among other things, by the mortgage crisis (2007)
Best neighborhood in which to shoot a movie, Leader of Culture (2015)
Best Neighborhood to Run Through in the Chicago Marathon (2018)
Best neon sign to evoke the good life (2002)
Best neon to make your Instagram feed glow (2019)
Best new bikeway (2013)
Best new building built in the last year or so (2009)
*Best new career for deposed Channel 5 news reporter Amy Jacobson (2007)
Best new CTA station (2012)
*Best new feature of the newly redesigned Tribune (2008)
*Best new gig for the Reverend Jeremiah Wright (2008)
Best new idea for public transportation (2013)
Best new innovative civic art event (2014)
*Best new name for Humboldt Park (2007)
Best New Name for the Trump International Hotel and Tower (2017)
Best New Neighborhood Downtown (2018)
*Best new nickname for Sam Zell (2008)
Best new perfume (2013)
*Best new piece of architecture (2008)
Best new online radio station (2014)
Best new open-air co-working space (2015)
Best new sports heroes to worship (2016)
Best New Sports Hero (and the Only Player Making the Bears Watchable) (2017)
Best new tourist attraction (2009)
*Best new work of architecture finished in the last year or so (2013)
Best newish downtown attraction (2012)
*Best newly minted Chicago celebrity (2008)
Best Newly Preserved Ghost Sign (2017)
Best Newspaper Front Page So Wrong It’s Right (2017)
*Best newsroom street level fish bowl (2009)
*Best next career for failed gubernatorial candidate Scott Lee Cohen (2010)
*Best next career for Jesse Jackson, Jr. (2010)
Best next dubious mascot for Chicago after “Chalkie” (2009)
Best next media moguls (2011)
*Best next neighborhood to gentrify, now that Humboldt Park’s on its way (2007)
Best next next next Wicker Park (2013)
*Best next thing for the city to privatize after selling off Midway Airport and the parking meters (2008)
*Best next thing for the state to privatize after selling off the Illinois Lottery (2008)
*Best next Twitter subject for Dan Sinker of @MayorEmanuel fame (2011)
Best niche website (2010)
Best nickname for that really enormous snowstorm last February (2011)
*Best nickname for the cops on Segways that patrol the parks (2007)
*Best nickname from the Joey Lombardo mob trial (2007)
Best non-corporate neighborhood (2013)
Best novelty Twitter account (2012)
Best obituaries (2019)
Best odd monument and tribute to The Great Migration (2015)
Best oh-so-Chicago scandal of 2015 (2015)
*Best opening paragraph from the memoirs of Richard M. Daley (2010)
*Best opening paragraph of an imaginary staff memo from Mayor Rahm Emanuel (2012)
Best organization working to decrease pretrial incarceration (2019)
*Best outcome from the Chicago Public Schools teachers strike (2012)
*Best outcome of the CNN miniseries “Chicagoland”  (2014)
Best outdoor make-out spot (2010)
*Best outing on Metra, CTA or other public transit lines (2007)
Best Park To Escape the Buzz of the Loop (2017)
Best part of the 2012 Chicago Cultural Plan (2012)
Best part of the 2012 Chicago Cultural Plan most likely to actually happen (2012)
Best path to take a romantic walk at night (2013)
*Best personal encounter with a Chicago cop, that may or may not have ended up with you getting beat down, and may or may not have been videotaped and shown on television (2007)
Best On-the-Rise Photographer to Capture Drag Chicago (2018)
Best place for a kid’s outing (2015)
Best place for a romantic stroll (2002)
Best place for an intellectual shoving match about the role of design in the City with a capital C (2015)
Best place for dummies (2011)
Best Place in the City to Witness in Stunning Detail the Juxtaposition Between Man’s Need to Industrialize and Nature’s Will to Persevere (2017)
Best place for children of the nineties to reminisce (2012)
Best place to actually get work done (2016)
*Best place to be in Chicago when the Ebola plague hits (2014)
Best place to chill out (2011)
Best place to drink in the forest preserves (2002)
Best place to enjoy a bag lunch by the river (2012)
Best place to experience Chicago’s famous wind (2016)
Best place to feel part of the cityscape (2019)
Best place to find a panhandler (2007)
Best place to find people who are not necessarily rich but dress well (2012)
Best place to flaunt your genderfuck style (2013)
Best place to get a haircut, Leader of Culture (2015)
Best place to get lost in a crowd (2007)
Best place to get on Lake Shore Drive northbound from downtown (2007)
Best place to get on Lake Shore Drive southbound from downtown (2007)
Best place to get your geek on (2016)
Best place to go and watch dogs (2019)
Best place to go when you need a nature fix (2016)
Best place to hide twenty-three guns (2019)
Best place to meditate outdoors in safe seclusion (2015)
Best place to nonchalantly check out the opposite sex (2008)
Best place to not stand on the El (2012)
*Best place to people watch (2013)
Best place to pretend you are outside during a Chicago winter, Leader of Culture (2015)
Best Place to Protest (2017)
Best place to see grown Chicagoans acting like little kids (2014)
Best place to see random street performers who will blow your mind, Leader of Culture (2015) 
Best place to see tattoos, piercings, dreads and sweet rides (2012)
Best place to smell the chocolate cloud (2011)
Best place to spot an alligator (2008)
Best place to spot Walking Guy (2012)
Best place to stop on the lakeshore bike path (2016)
Best place to wait out a Chicago winter (2016)
Best place to walk off writer’s block (2015)
Best place to witness the crushed bones of the past and the tenuous specters of the future (2019)
Best Pontoon Gardens (2017)
Best Pool in an Urban Landscape (2018) 
*Best potential buyer of Tribune Publishing, among those names bandied about (2013)
Best post-WWII motel sign still standing, though the motel is long gone (2011)
Best predictive text on the likely fate of the James R. Thompson Center (2019)
*Best prison name for Blago (2012)
Best Promise Unkept (2017)
Best proposal for Chicago’s next landmark (2010)
Best public edifice to name for Obama, now that Rahm’s yanked his name off the elite North Side school  (2014)
Best public restroom (2013)
Best public service act by someone who has never served a day in public office (2017)
Best public space to read classic Chicago poetry and prose (North Side) (2015) 
Best public space to read classic Chicago poetry, prose and drama (South Side) (2015)
Best Rahm policy reversal (2012)
Best Rat (2018)
Best Rats (2018)
Best Reaction To Nobody’s Favorite Local Meathead (2017)
Best real life example of haters gonna hate (2015) 
Best reason for Chicagoans to boast to their lefty West Coast friends (2012)
Best reason for the real estate market to turn around soon (2009)
Best reason for vexillologists to live in Chicago (2013)
Best reason not to diss Richard Roeper (2007)
Best reason to appreciate the CTA’s long-lingering “slow zones” on the Blue Line (2007)
Best Reason to Believe Television is Chicago’s Next Medium Takeover (2018) 
Best Reason to Care About the Bulls (2017)
Best reason to endure months of downtown roadwork (2014)
Best Reason to Go to Brookfield Other than the Zoo (2018) 
Best reasons to stop seeing red over grungy El stations (2014)
Best reason to wonder if Mayor Daley is really in charge (2007)
Best rebuke of a Mercer-nurtured rabble-rouser(2019)
Best refuge from drunken frat boys and other urban miseries (2011)
*Best relic of the “Devil in the White City” era still extant (2007)
Best Remains of Chicago’s Beer Brewing Glory (2017)
Best Remedy for the Cubs Year-Long World Series Hangover (2017)
Best reminder that no one is safe and the machine will swallow us all (2015)
Best reminder of Chicago’s grimy industrial past close to downtown (2015)
Best reproduction of a Monopoly game square (2010)
*Best Republican candidate for US President (2007)
Best response to Donald Trump’s race-baiting rant about Chicago (2016)
Best rock icon spotted on the CTA (2014)
*Best Rod Blagojevich accomplishment of the past year and we’re being serious here (2009)
Best ruins (2015)
Best Russian orthodox church designed by an American architect (2012)
Best safety stance by a Chicago team (2019)
Best secret flower patch in Chicago (2012)
Best shot fired in “Chiraq” firefight so far (2015)
Best shoutout to Chicago’s gun violence by a national late-night talk-show host (2013)
Best Sign of Eternal Real Estate Cycles (2017)
Best sign of progress of maintaining CTA infrastructure (2019)
Best sign of the Armageddon in 2008 (2008)
Best sign on the Kennedy Expressway (2019)
*Best sign that Rahm is not Richie (2011)
*Best sign that Rosie is not Oprah (2011)
Best single-purpose fake Twitter account (2013)
*Best slogan for Chicago to make the world forget about all those nasty murders they keep hearing about (2012)
Best smelling bike lane (2011)
Best-smelling El stop (2013)
Best social service fundraiser party (2014)
Best South Side intersection for old-school dining and jazz (2010)
Best sports argument (2016)
Best spot for celeb sightings (2010)
Best Springtime Reminder We’re All Doomed (2018) 
Best square glimpse of the 1970s Chicago singles bar (2019)
Best stereotypical, incomplete, single-minded documentary depicting the black men of Chicago (2014)
Best story… period (2014)
Best street to drive down (2007)
*Best suggestion for a more appropriate location for the controversial TRUMP sign (2014)
Best Tax Repeal (2017)
Best temperance fountain (2016)
Best Temporary Wall Mural (2018) 
Best ten reasons not to leave Chicago (2011)
Best “The Summer of Ye” Media Tour Stop (2018)
Best thing about Chicago, Leader of Chicago (2015)
Best thing about Governor Rauner’s proposed Thompson Center teardown (2015)
Best thing about Michael Ferro turning Tribune Media into “Tronc” (2016)
*Best thing about Millennium Park besides the Bean (2009)
Best thing about not having the Lucas museum (2016)
Best thing about Snowmageddon (2011)
Best thing about the otherwise-disastrous Bruce Rauner administration  (2015)
*Best thing about that whole NATO Summit business (2012)
Best thing about the Bloomingdale Trail, aka The 606 (2015)
*Best thing about the new Divvy bike-sharing system (2013)
Best thing about the new parking meters (2009)
*Best thing about the return of Bill & Walter to Channel 2 (2010)
Best thing to happen to Chicago nonprofits (2009)
*Best thing to name after Richard M. Daley (2010)
Best thing to never do on the Blue Line (2013)
*Best thing we can expect from the Tribune sale (2007)
Best thorn in the side to Rahm Emanuel (2016)
Best threesome (2011)
Best touch of Paris (2007)
Best-to-date-but-certainly-not-last first-person account of the slow and painful death of the Chicago Sun-Times  (2015)
Best Toilet for Examining Plant Life (2017)
Best Train to Take During December (2018)
Best transvestite watching (2010)
Best Tweetathon, Leader of Culture (2015)
*Best tweeting by a local news or politics personality (2009)
Best Twitter dis of the City Council (2019)
Best under-the-radar local nonprofit (2007)
Best underground cafe (2014)
*Best unexpected manifestation of the smoking ban (2008)
Best unhinged Twitter account linked to local public transit (2013)
Best university from which to be denied tenure (2007)
Best unknown state park within the Chicago area (2015) 
Best unrecognized historic tragedy (2012)
Best unrecognized, historical African-American female union and socialist labor hero (2016)
Best unrecognized landmark to Chicago’s gay community (2008)
Best Uplift the Drive (2018)
Best update to Chicago’s bike infrastructure (2015)
Best use of empty lots (2019)
Best use of $100 million (2012)
Best view from a parking garage (2007)
Best view of the Chicago skyline from a car (2015)
*Best view of the Lake (2009)
Best view of the skyline you never expect (2012)
Best view without the Lake (2009)
Best warning North Branch is done (2019)
Best warning that Wicker Park is done (2019)
Best warning Westtown is done (2019)
Best warrior against the hegemony of car culture (2009)
Best way to anger a long line of commuters (2013)
*Best way for Chicago’s Olympics to outdo the Beijing Olympics (2008)
Best way to cement your status as a Chicagoan (2013)
*Best way to describe Chicago weather (2012)
*Best way to end Chicago’s budget woes (2010)
*Best way to end the city’s budget crisis (2009)
*Best way to end the city’s budget crisis, which we thought we’d never have to ask again after we posed the question five years ago, but here we are (2014)
Best way to explore Chicago, Leader of Culture (2015)  
Best way to feel like you’re helping the homeless without much effort (2012)
Best way to fight parking scarcity (2015)
Best way to fold a map (2019)
Best way to impress a transplant Chicagoan using only a bookshelf (2015) 
Best way to keep your balance on the El (2013)
Best way to leave the city (2019)
Best way to not solve a murder crisis (2016)
Best way to relive the terrors of your daily commute (2012)
Best Way to Restore your Faith in Humanity (2017)
Best way to squander $2.75 billion and defund public transportation (2013)
Best way to tour the city for the canine crazy (2019)
Best way to try and solve a murder crisis for political points rather than results (2016)
Best way to unite Chicago (2019)
Best way to waste $130,106.15 (2019)
Best “Wild Kingdom In the Big City” moment, Leader of Culture (2015)
Best winter sanctuary, Leader of Culture (2015)
Best words to be rendered in 20-foot serif fonts on building facades (2014)
Best zoological additions to Chicago (2012)
Made in Chicago: Best Chicago contribution to LGBTQ history (2019)
Made in Chicago: Best Chicago-made activist (2019)
Made in Chicago: Best Chicago-made charity (2019_
Made in Chicago: Best Chicago-made female skate team (2019)
Made in Chicago: Best example of street business acumen (2019)
Made in Chicago: Best gift to the game (2019)
Made in Chicago: Best persistent name for fizzy nectar (2019)

CULTURE & NIGHTLIFE

Best of the Best: Berlin (2002)
Best of the Best: Brew and View at the Vic Theatre (2002)
Best of the Best: Buddy Guy’s Legends (2002)
Best of the Best: Chicago Botanic Gardens (2002)
Best of the Best: Chicago Cultural Center (2002)
Best of the Best: Chicago Symphony Orchestra (2002)
Best of the Best: Delilah’s (2002)
Best of the Best: Doc Films, University of Chicago (2002)
Best of the Best: Empty Bottle (2002)
Best of the Best: Field Museum (2002)
Best of the Best: Fireside Bowl (2002)
Best of the Best: Frank Lloyd Wright Home and Studio (2002)
Best of the Best: Garfield Park Conservatory (2002)
Best of the Best: The Gene Siskel Film Center of the School of the Art Institute (2002)
Best of the Best: Goodman Theatre (2002)
Best of the Best: Green Mill (2002)
Best of the Best: The Hideout (2002)
Best of the Best: House Music (2002)
Best of the Best: International Museum of Surgical Science (2002)
Best of the Best: Jazz Showcase (2002)
Best of the Best: Jimmy’s Woodlawn Tap & Liquor Store (2002)
Best of the Best: Lyric Opera (2002)
Best of the Best: Matchbox (2002)
Best of the Best: The Metro (2002)
Best of the Best: Museum of Science and Industry (2002)
Best of the Best: Music Box (2002)
Best of the Best: Newberry Library (2002)
Best of the Best: Northalsted Market Days (2002)
Best of the Best: Old Town School of Folk Music (2002)
Best of the Best: Printers Row Book Fair (2002)
Best of the Best: The Second City (2002)
Best of the Best: Steppenwolf Theatre Company (2002)
Best of the Best: Studs Terkel (2002)
Best of the Best: Tuman’s Alcohol Abuse Center (2002)
Best 12×12 solo exhibition at the Museum of Contemporary Art (2010)
Best 1990s Wicker Park ghost sign (2019)
Best abiding sorrow mistaken for performance art (2007)
Best actor to make Chicago proud this year (2009)
Best acoustics in a music club bathroom (2015)
Best adult show-and-tell experience (2015) 
Best advocate for queer theory in art (2014)
Best aerial and circus arts school (2016)
Best African music night (2013)
Best album covers by a local label (2014)
Best alkie end-of-nighter nightspot that we’ll never forget, or remember for that matter (2013)
Best all-ages, seasonal monthly lakefront event (2015)
Best all-nude cast (2013)
Best Amateur Gallery (2018)
Best (and oldest) telescope in America (2019)
Best antiquities museum (2019)
Best arcade bar (2019)
Best Argument to Join Sober (2017)
Best alternative art-space fundraiser (2009)
Best alternative dance club (2007)
Best alternative gallery show in the past year (2014)
Best alternative to EXPO Chicago 2016 (2016)
Best amateur-band regional touring nightspot (2013)
Best anniversary fest for a music empire now gone (2011)
Best anniversary fest for a music empire still living (2011)
Best annual music festival (2007)
Best annual public art event (2012)
Best apartment gallery (2014)
Best apology for interrupting an opening-night performance (2013)
Best approximation of South Beach Miami (2007)
Best architectural restoration (2007)
Best art beer (2013)
Best arts club (2015)
Best art exhibit at a gallery (2013)
Best art comeback (2013)
Best art exhibit in Second Life (2007)
*Best art exhibit (in the last year or so) (2007)
*Best art exhibit (in the last year or so) (2008)
*Best art exhibit (in the last year or so) (2009)
*Best art exhibit (in the last year or so) (2010)
*Best art exhibit in the last year or so (2011)
*Best art exhibit in the last year or so (2012)
*Best art exhibit in the last year or so (2013)
*Best art exhibit (in the last year or so) (2014)
Best art exhibit (in the last year or so) held in the suburbs (2010)
Best art exhibition about architecture in an architecturally significant building (2011)
Best art-exhibition catalogue design (2011)
Best art exhibition catalogue design in the last year or so (2012)
Best Art Fair Shuttle Bus Service (2018)
*Best art gallery (2011)
Best Art Institute of Chicago curator you’ve never heard of (2016)
Best art interview LP (2012)
Best art in a coffee shop/bakery, Leader of Culture (2015) 
Best art museum that is not an art museum (2012)
*Best art-opening parties (2008)
Best art project to effect change in the criminal justice system (2014)
Best art reading (2012)
Best art road trip (2013)
Best art school for hobbyists (2011)
*Best art show (in the last year or so) (2002)
Best art YouTube channel (2014)
Best artist bookstore (2009)
*Best artist who has yet to play Lollapalooza but should (2008)
Best artist TED Talk that wasn’t actually A TED Talk (2015)
Best artistic response to bad art (2015)
Best arts center that also offers shamanism courses (2014)
Best artwork worth saving from destruction (2007)
Best atmosphere for musical improv (2015)
Best attempt to save street art from graffiti blasters (2019)
Best authentic German pub interior (2013)
Best avant-garde resurrection (2016)
Best awkward silence (2013)
Best backyard gallery (2015)
Best band that plays only a thirty-minute set (2019)
Best bar above Lawrence Avenue (2008)
Best bar couch (2015)
Best bar for a first date (2016)
Best bar for a going-away party (2016)
Best bar for free popcorn and NES video gaming (2011)
Best bar standup comedy night (2013)
Best bar that emulates your father’s basement (2007)
Best bar to close before it became legendary (2014)
Best bar to contemplate the universe over checkers (2016)
Best bar to drink and daydream about Prohibition (2016)
Best bar to drink at to avoid watching the Mets eliminate the Cubs in the ever-loving postseason (2015)
Best bar to drink well, eat well and play pool—without fussy, fancy ice cubes (2016)
Best bar to get a martini and manicure (2012)
*Best bar to have a conversation in (2008)
Best bar to pick up a molecular biologist (with patents) (2002)
Best bar to pretend you’re someone else (2007)
Best bar to see a reading (2009)
Best bar to smoke on New Year’s Eve, before the non-smoking ban goes into effect (2007)
Best bar to time travel in (2010)
Best bar turned rock venue (2013)
Best bar-turned-rock venue (in the last year or so) (2007)
Best barcade game (2016)
Best basement gallery (2011)
Best bathroom boot camp (2009)
Best big-budget horror comedy (2015)
Best Bill Daley Takedown (So Far) (2018)
Best Bingo Bar (2017)
Best bit of a twelfth-century monastery in Chicago (2016)
Best black sports voices (2016)
*Best blues club (2011)
Best book-critic inspiration (2013)
Best book to get laid with (2014)
Best book written by a local author (in the last year or so) (2008)
Best bookstore-and-bar one-two punch (2015)
Best booth at EXPO Chicago (2013)
Best Bossa Beat (2017)
*Best bowling alley (2008)
Best Break In Localized Reporting (2018) 
Best breakout booze and lit reading series (2013)
Best Breakout Contemporary Dance Artist (2017)
Best Breakout Dance Artist on Political Themes (2017)
Best Breakthrough Design Artist (2017)
Best bricolage (2014)
Best bridge to live under (2012)
Best British Invasion since the Beatles (2014)
Best brother/sister garage rock band (2010)
Best burgeoning Chicago film career (2007)
Best by-appointment-only art gallery (2016)
Best cabaret (2002)
Best Café for Artistic Open-Minded Seniors and Anybody Else Who Wants To Come
*Best candidate for “One Book Chicago” still untapped (2007)
Best cantankerously comedic crooner and pleasantly perverse pianist (2015)
Best carriage house exhibition space (2016)
*Best celebrity art show to bring to Chicago after Bowie at the MCA (2014)
Best Cellist-Composer (2017)
Best Chicago-area rock band that has been around for fifty-five years (2019)
Best Chicago art boosters (2008)
*Best Chicago-as-Gotham moment in “The Dark Knight” (2008)
Best Chicago-based Web Series About Witches (2017)
Best Chicago comic book convention (2011)
Best Chicago drinking blast from the past (2013)
Best Chicago film proffering a swift fuck-you to Trump (2019)
Best Chicago Public Library for an Afternoon Punk Rock Show (2017)
Best Chicago Rap Lyric About Social Media (2018)
*Best Chicago record label (2011)
Best Chicago-related TV series (2013)
*Best Chicago theater company (2013)
Best Chicago theater company not in Chicago (2013)
Best Chicago Touring Opera Company (2017)
Best Chicago version of the Eurythmics (2011)
Best Christmas festival (2008)
Best classic dive bar that’s not really a dive bar (2019)
Best cocktail and salsa combo (music, we mean) (2016)
Best collab (doing something they should have done a looooooonnnnnngggg time ago) (2014)
Best collaborative accomplishment in the arts (2011)
Best collaborative multimedia dance performance (2015)
Best college campus art gallery (2008)
*Best college campus art gallery or museum (2013)
*Best college radio station (2008)
*Best college radio station (2013)
Best combination of elasmobranchology and potty humor (2012)
Best combo of Chicago cultural traditions (2013)
Best Comic Book to Preorder by a Chicagoan about a Chicagoan (2018)
Best comic-relief sidekick (2009)
Best Comix Fest That Has Come Into Its Own (2017)
Best commercial gallery revolt (2015)
Best commercial gallery show in the past year (2014)
Best commercial gallery show in the last year (2015)
Best Community Art Center on the Planet (2018)
Best community-based video game, Leader of Culture (2015)
Best concentration of employees who are also recording artists (2013)
Best conceptually complicated exhibition to be mounted in what is essentially an office (2012)
Best contemporary dance company you’ll never see again (2013)
Best controversy over a theatrical review (2013)
Best controversy where there was none (2011)
Best convention to combine comic-book culture, anime, manga, cosplay, video games, Power Rangers, Dr. Who, Game of Thrones, cult movies, cult TV, cult pop cult paraphernalia, in one big three-day-long, multi-floored jambalaya of fanboys and gamer girls, wannabes and gurus, rising talents, panelist pontificators, free screenings, and featured guests, photo op stalkers, pop artifact hawkers, cosplay gawkers and merchandise floor walkers (2015)
Best corner for public evangelizing (2012)
Best Countertenor (2018) 
*Best country album by a Chicago artist (in the last year or so) (2002)
Best country bar to belt Zac Brown Band without shame (2012)
Best cover band that is also a drinking game (2016)
Best creative use of an arboretum (2011)
Best creepy/cool art exhibit (2014)
Best critical art project in Chicago this year (2012)
Best crowd-sourced event in a museum (2011)
Best crowd-sourced Chicago History Museum exhibit (2015)
Best Culture-Filled Road Trip (2018)
Best curatorial hire of the year (2015)
Best Curiosity-Triggering Way to Get You to Engage with the Chicago Art and Design Scene (2018)
Best current Chicago band that sounds like a post-punk group from 1982 (2013)
Best dance advocacy effort (2015)
*Best dance club (2011)
Best dance company to take a date who’s afraid of contemporary dance (2014)
Best dance incubator (2014)
Best dance festival (2016)
Best dance/performance art crossover (2016)
Best dance performance by recent graduates (2016)
Best dance residency (2016)
Best dance show about a presidential administration (2015)
Best date move (2013)
Best decorated reading room in the Loop (2016)
Best design slogan (2013)
Best decade-long queer dance party (2015)
Best digital tour through a museum’s collection (2011)
Best dining experience during a Federal raid (2015)
Best dinner party with fascists, anarchists and feminists (2012)
Best DisArt Performance (2017)
Best Display of Public Affection (2017)
*Best dive bar (2013)
Best dive bar featuring all-German beer (2010)
Best dive bar that is not yet overrun with hipsters (2016)
Best divey 4am LGBT bar without wood paneling (2013)
Best DIY Creator of Safe, Theatrical Spaces in Chicago (2017)
Best DJ masquerading as a lawyer (2014)
Best downtown dive bar you’ve never heard of (2013)
Best drag actor (2016)
Best drag/art fusion (2013)
Best drag performer (2007)
Best drag queen pickup spot (2013)
Best-dressed burlesque performer (2015)
Best-dressed improvised jazz musician (2014)
Best drink with a view (2012)
Best Dunk on The Late, Unlamented Tronc (2018)
Best Effort by Elvis to Do a Crossover Tune that References Chicago in Winter (2018)
Best eighties dance night (2010)
Best El station art installation (2013)
Best embarrassing journal reading (2015)
Best emerging art gallery (2011)
Best emerging artist team-up (2014)
Best emerging dancer (2016)
Best emerging endurance art performance (2015)
Best enigma of an exhibition (2013)
Best Enshrinement of the Cultural Edifice Complex (2017)
Best Evanston-based arts advocate (2014)
Best event to see (and swoon over) Ira Glass in person (2012)
Best example of overcoming secondcityitis (2007)
Best example of using music for cultural awakening (2014)
Best excuse to revisit the eighties (2011)
Best exhibition design (2013)
Best exhibition design (2014)
Best exhibition in the last year (2015)
Best exhibition to see for aspiring sculptors (2014)
Best expatriate turned international music community ambassador (2013)
Best facelift on a North Side bar (2012)
Best fact about Chicago wildlife (2013)
Best Fall Hideout (2018)
Best 50-cent beer night (2011)
Best family theater experience that might actually entertain the whole family (2015)
Best “feel good” bangers to get you through the impending winter (2019)
Best Festival Afterparty (2017)
Best Films That Capture The Sensation Of Chicago, An Essay (2016)
Best first date (2010)
Best five dollars you can spend on a Thursday night (2008)
Best “flow” object manipulation dance event (2015)
*Best foreign cultural center in Chicago (2012)
Best foreign film festival in Chicago (2012)
Best foreshadowing of the smokers purgatory to come (2007)
Best free twice-monthly stand-up show (2015)
Best 4am bar worth a cab ride (2007)
*Best film festival (2014)
Best flow artist in Chicago (2016)
Best Frank Sinatra avatar (2015)
Best free art-exhibition catalogues (2011)
Best Free Attraction When Winter Feels Endless (2018)
Best free indie parties sponsored by a corporation (2011)
Best free intra-city touring dance series (2015) 
Best free show (2013)
Best free theater (2014)
Best Free Weekly Stand-up Showcase (2018)
Best Friday night dance party no one knows about (2008)
Best funky theater venue (2012)
Best fusion (2015) 
Best gallery exhibition catalogues (2014)
Best gallery on a telephone pole (2019)
Best gallery show in the last year (2009)
Best gallery showing Chicago artists (2011)
Best gallery space located in a bathroom (2009)
Best gallery to people-watch (2014)
Best gathering of typography nerds (2019)
Best Genre Fest for Film (2018)
Best German heritage event (2012)
Best Gospel Group (2017)
Best graffiti on a place you have no idea what it is (2019)
Best Greek Music Concert Promoter (2017)
Best Gregorian Chant (2018)
Best group booty call (2013)
*Best guess as to where Billy Dec is and what he’s doing right now (2009)
Best handmade book publisher we’re all really rooting for (2013)
Best Hard-Boiled Writing Advice (2018)
Best hidden architectural gem that’s also a gallery (2019)
Best high-school murals to get teenaged boys interested in art (2009)
Best high-school spoken-word competition (2015)
Best hipster-free bar in Wicker Park/Ukrainian Village (2009)
Best hipster specialty dance night (non-Soul Night division) (2011)
Best holiday movie repertory tradition (2019)
*Best holiday-themed theatrical production (2010)
Best homage to a beloved Chicago artist and teacher (2015)
Best honky tonk hillbilly bar left over from Chicago’s second great migration (2015)
Best Hope for Chicago Bears’ Future (2018)
Best hope to make us forget Chief Keef ever existed (2014)
Best House Music Podcast (2017)
Best houseplant garden in an art gallery (2012)
Best Housewife to Defect to Chicago (2017)
*Best hypothetical story line for “Trapped in the Closet” chapter 23 (2007)
Best “I gotta go back there just to see her” bartender (2011)
Best “I gotta go back there just to see her” hostess (2011)
*Best idea for Desiree Rogers to use to revive Chicago icon Ebony/Jet (2010)
*Best idea for Hugh Hefner to use to revive Chicago icon Playboy (2010)
Best idea to improve the moviegoing experience (2013)
Best illumination of a heartbreaking problem that few know about (2014)
*Best imaginary Twitter post by Studs Terkel (2009)
Best improv club (2011)
Best improv troupe (2015) 
Best improvisational dance public forum (2015)
Best Inadvertent Second-Run Art-House (2017)
Best independent comics event (2012)
Best independent curator (2013)
Best independent feminist bookstore you could own (2013)
Best individual accomplishment in the arts (2011)
Best initiative to make dance free and accessible (2014)
Best insider’s view of Chicago’s underground art scene (2013)
Best Instagram-based coverage of a Chicago art brouhaha (2016)
Best institutional accomplishment in the arts (2011)
Best international showing of Chicago artists (2012)
Best Irish bar (2008)
Best ironically situated art show (2019)
Best irreplaceable loss for the culture (2011)
Best itinerant museum (2019)
Best itinerary for creeps (2002)
Best Japanese-inspired garden (2007)
Best Jazz Age relics (2016)
*Best jazz album by a Chicago artist (in the last year or so) (2002)
*Best jazz club (2011)
Best jazz musician to make us proud in the near future (2002)
Best Jazz-Themed Benefit Impresario (2017)
*Best John Hughes movie set in or around Chicago (2009)
Best judicial disloyalty to a colleague (2017)
*Best Kanye West lyric he’ll likely never write (2013)
Best kinky dance party (2013)
Best kite outing (2016)
Best lakefront transplant trapeze school (2019)
Best Lakeview “Wait, what neighborhood am I in?” bar (2016)
Best late-night holiday-themed theatrical production (2010)
Best Least Likely Music Venue (2018)
Best leave me the hell alone! I just want to go to a BAR bar (2016)
Best lesbian karaoke (2013)
Best LGBTQ beach party (2016)
Best LGBTQ dance and performance program (2016)
Best LGBTQ Performance Series (2017)
Best Life In Wartime Moment (2018) 
Best Lincoln Park Zoo experience for adults (2019)
Best literary idea to change social disorder (2016)
Best literary impulse (2012)
Best literary magazine for young adults (2015)
Best literary monument (2010)
Best Live Jazz Where You’d Least Expect Live Jazz (2017)
*Best live lit event (2014)
*Best live music show (in the last year or so) (2009)
Best live rendition of “Total Eclipse of the Heart” onstage (2013)
Best live sound (2019)
*Best local actor (2010)
*Best local arts, culture or nightlife blog (2009)
Best local band to almost make the cover of Rolling Stone (2011)
Best local Barack Obama propaganda (2008)
*Best local dance company (2012)
*Best local DJ (2010)
Best local mainstream-comic-book creator (2007)
*Best local music festival (2010)
Best Local Music Podcast (2017)
Best Local New Academic Title on Dance and Performance Art (2017)
Best local publisher (2002)
Best local talk show, Leader of Culture (2015)
Best local TED alternative (2012)
Best local weekday DJ residency (2016)
Best location with freshly poured concrete (2016)
Best longest-running show in Chicago (2014)
Best-looking band (2007)
*Best-looking bartenders or wait staff (2007)
Best Lost Boys treehouse gallery (2014)
Best lost-and-found (or how to bring your idol to tears) story, Leader of Culture (2015) 
*Best mainstream movie theater (2010)
Best marching-band documentary by the best Chicago artist who is not a Chicago artist (2012)
*Best martini selection (2008)
Best MC not named Noname (2016)
Best MC not named Vic Mensa (2016)
Best Meetup Discussion Group (2017)
Best melding of older jazz and younger local talent (2019)
*Best memory shaken loose by the re-release of Liz Phair’s “Exile in Guyville”(2008)
Best merger of sports and art (2013)
Best microbrewery in a historic district (2012)
Best midweek jazz boite (2011)
Best missing attraction in Chicago (2002)
Best mobile art project (2014)
Best monthly improvisational dance gathering (2015)
Best monthly queer dance party (2007)
Best Monthly Stand-up Showcase (2018)
Best most-ubiquitous Chicago musicians (2019)
Best mother/daughter directorial effort (2013)
Best Movement Director (2017)
Best Movie-House Enshrinement of a Good Review (2017)
Best museum exhibit with really really really ambiguous educational value (2009)
Best music festival footwear (2016)
Best music on a Thursday, Leader of Culture (2015)
*Best name other than “Nothing Like the Holidays” for renaming the movie once known as “Humboldt Park” (2008)
Best NaNoWriMo effort (2016)
Best National (and International) Fashion Takeover of Any City (2018)
Best national tribute to Milos Stehlik so far  (2019)
Best neighborhood music fest (2010)
Best new album by a local artist (in the last year or so) (2007)
Best new art gallery (2012)
Best new art gallery on a car bumper (2013)
Best New Art Historical Monument Restoration (2017)
Best new art residency (2010)
Best new artist book artist (2012)
Best new author title from a local indie press (2014)
*Best new bar (opened in the last year or so) (2007)
*Best new bar or club (opened in the last year or so) (2009)
*Best new bar or club (opened in the last year or so) (2011)
*Best new bar or club opened in the last year or so (2012)
*Best new bar or club opened in the last year or so (2013)
*Best new bar (opened in the last year or so) (2002)
*Best new bar (opened in the last year or so) (2008)
*Best new bar or club (opened in the last year or so) (2014)
*Best new bar or nightclub (opened in the last year or so) (2010)
Best new book about Chicago’s sordid past (2007)
*Best new book by a Chicago author in the last year or so (2014)
*Best new Boystown spot (2007)
Best new cabaret venue (2015)
*Best new Chicago band (2002)
Best new clothing label 2019)
*Best new club (opened in the last year or so) (2007)
Best new communitarian art festival (2014)
Best new community-service festival (2015) 
*Best new dance club (opened in the last year or so) (2002)
Best new dance venue that was already a dance venue renamed after a still-physically-existing-but-no-longer-a-venue-for-dance venue (2013)
Best new DIY event space (2014)
Best new folk music act (2014)
Best new free event in Chicago (2007)
Best new gallery of the future (2011)
Best New Garage Art Space You Haven’t Heard Of (2017)
*Best new gay or lesbian club (opened in the last year or so) (2002)
Best New Graphic Novel by a Chicago Artist (2017)
Best new high-touch design venue (2014)
Best New House Music Picnic Gathering (2017)
Best new housing for artists (2014)
Best new improvisational dance performance (2015)
Best new industrial label (2019)
Best new jazz venue (2015)
Best new literary event (2011)
Best Bar to Drink for a Cause (2017)
Best new literary festival (2013)
Best new literary salon (2019)
*Best new live music club (opened in the last year or so) (2002)
Best new live music venue (2009)
Best New Locally Produced Internet TV Series that Should Have Won an Emmy (2017)
Best new Monday night dance party (2008)
Best New Movie Palace Renovation (2017)
Best new mural (2011)
Best new music festival  (2019)
Best new music venue (2008)
*Best new nightclub (opened in the last year or so) (2008)
*Best new “nom de guerre” for Chief Keef to make everyone forget about the tragic Lil JoJo business (2012)
Best new online artist-run publication (2016)
Best New Performance Art Discussion Program (2017)
Best new podcast (2008)
Best new queer-centric variety show (2019)
Best new record-label mogul, workwear pioneer and proud owner of three chickens (2013)
Best new restaurant/lounge hybrid (2002)
Best new scene to be seen (2009)
Best new show by a MacArthur “genius” (2013)
Best new singles event (2007)
Best new source of empowerment for black artists (2014)
Best new strides taken for gender inclusivity in art school (2014)
Best New Taste From Big Star (2017)
Best new theater company for intellectuals (2013)
Best new tool for Impressionism nerds (2014)
Best new trend (2009)
Best new trend in free (or damn close) Chicago theater (2011)
Best new venue for experimental arts (2013)
Best New Visual Art/Performance Crossover (2017)
Best new world record held by Chicagoans (2009)
Best new University of Chicago art space (2015)
Best News For The Chicago Reader (2018)
*Best next foe for the rival film critic who smacked Roger Ebert at a screening (2008)
Best next local Twitter tracker after the “Tamale Guy tracker” (2009)
*Best next role for Jeremy Piven (2007)
Best night at the Music Box Theatre (2007)
*Best night ever at Smart Bar (2007)
Best non-book at the Newberry Library (2019)
Best non-senior, non-student discount (2008)
Best nonsense for your buck (2007)
Best nontraditional portrait (2013)
Best North Side artist lecture series (2015)
Best nude in public event (2016)
Best one-man-band (2015)
Best one-man show by a convicted rapist with a face tattoo (2013)
*Best ongoing event/night at a dance club (2002)
Best ongoing improvisational dance project (2015)
Best ongoing local music showcase (2015)
Best onstage birth (2013)
Best onstage magic (2015)
Best onstage mess-making (2008)
Best onstage rock band that never plays a song (2013)
Best onstage use of live rats (2013)
Best open mic (2010)
Best open mic host (2015)
Best Open Mic Just for Teens (2017)
Best open-studio holiday art sale (2009)
Best opportunity for emerging artists (2013)
Best organization fostering the next generation of artists (2019)
Best outdoor amphitheater that isn’t the Pritzker Pavilion (2019)
Best outdoor bar (2010)
Best painter under the age of 25 (2009)
Best painting show (in the last year or so) (2011)
Best party where you won’t be surrounded by bros (2014)
Best performance art exhibition (2016)
Best performance art festival (2016)
Best performance art star under-recognized in his own hometown (2015)
Best performance lecture series (2016)
Best Performance Space Programming Revamp (2017)
Best petulant and profound art intervention (2014)
*Best piano bar (2009)
*Best piano bar (2014)
Best Pilsen backyard art/performance spot hidden gem (2015)
Best ping-pong bar (2012)
Best place for a birthday bash (2015)
*Best place for a first date (2008)
Best place for an unconventional haircut/color, Leader of Culture (2015)
*Best place for celeb sightings (2012)
Best place for Madonna madness (2010)
Best place to be around 50,000 costumes (2016)
Best place to be during the Air and Water Show (2019)
Best Place to Be Yourself (2018)
Best place to buy 78s (2015)
Best Place to Celebrate St. Patrick’s Day (2018)
Best Place to Dance and Eat Your Way through Day of the Dead (2018)
Best place to dance samba (2012)
Best place to drink champagne (2007)
Best Place to Explore Your Inner “Off the Wall” (2018) 
Best place to eye a boy toy (2009)
Best Place to Feel the Punk Rock Craze (2018)
Best place to fly your freakiest flag (2012)
Best place to get a Guinness float (2007)
Best place to get a one-dollar mug of Old Style (2009)
Best place to get drunk before 10am (2010)
Best place to get in touch with your inner Lemmy (2011)
Best place to get your pyromaniacal hippie on (2012)
Best place to get your stinkin’ wino on in greater Liquor Park (2007)
Best place to go when Lollapalooza rains out (2012)
*Best place to have a bachelor party (2010)
*Best place to have a bachelorette party (2010)
Best place to have Spring Break all summer (2007)
Best place to hear difficult, obscure and often excruciatingly loud experimental electronic music, Leader of Culture (2015) 
*Best place to hear world music year round (2012)
Best place to hook up with your future sugar baby or daddy (2013)
Best place to inhale Italian-American culture (2012)
Best place to play Anthony Haden-Guest (2014)
*Best place to play board games (2008)
Best place to play darts (2008)
Best place to pregame for a Stravinsky concert (2013)
Best place to pretend you’re on a tropical vacation (2007)
Best place to read Faulkner (2007)
Best place to say goodbye to your ex (2016)
Best place to see a film longer than most people get to sleep each night (2007)
*Best place to see an author reading (2010)
*Best place to see art films (2009)
*Best place to see art films (2014)
*Best place to see comedy (2013)
*Best place to see contemporary dance performances (2007)
Best place to see emerging artists at work (2008)
Best place to see Italian movies for free (2015)
Best place to see live world music now that HotHouse is gone (2007)
Best place to see movies outdoors (2002)
Best place to see work by emerging Chicago artists (2015)
Best place to tip the bartender (2007)
Best place to volunteer your time and have a good time while doing it (2008)
Best place to watch a legendary Chicago blues musician for free (2019)
*Best place to watch soccer on TV (2008)
Best Plan for A Destination Tourist Attraction (2017)
Best Polish pub with tiki ambiance (2010)
Best Polish Punk Band (2017)
Best political art performance reenactment (2012)
Best Post-Lollapalooza Club Set (2018) 
Best polyamory meet-up (2013)
Best Pop-Up Experience (2018) 
Best portrayal of hipsters (2013)
*Best post-Cubs-game bar (2008)
Best post-gallery drinks in a not-so-artsy neighborhood (2019)
Best Prince tribute (2016)
Best printmaking studio (2010)
Best private club for artists and artistes (2014)
Best production of a play you may have expected to be boring (2008)
Best Progressive Music Venue No Longer Under a Viaduct (2017)
Best proof that we’re not in Kansas anymore (2008)
Best public art failure (2011)
Best punk-rock karaoke (2016)
Best puppy art (2013)
Best qualitative data on Chicago’s art scene (2014)
Best queer cabaret (2015)
Best quiet museum space with a striking collection of contemporary art (2010)
Best Reading Series at 9pm on a Tuesday (2013)
Best real-life story to offer inspiration (2019)
Best “Real World” cast member from Chicago (2002)
*Best reality-show contestant from Chicago (2009)
Best reason not to go to Lollapalooza (2007)
Best reason to cheat (2009)
Best reason to concede “Say Anything” is so twentieth century (2007)
Best reason to drive to Aurora (2016)
Best Excuse to Go to Aurora (2017)
Best Place to Save $780 on Your Annual Entertainment Budget (2018) 
Best reason to go to Lollapalooza (2007)
Best reason to learn how to pronounce Marisa Wegrzyn’s last name (2007)
Best reason to look up (2007)
Best reason to sit still for three-and-a-half hours (2007)
Best Reason to Skip the Nutella Cafe (2017)
Best reason why we don’t deserve anything nice (2002)
Best reborn heritage event (2012)
Best reboot of a historic Chicago arts institution (2015)
Best Red Hots #Resistance (2018) 
*Best regular club night (2007)
Best regular magic show (2013)
Best regular trumpet gig (2010)
Best reminder of Chicago’s old Serbian community (2012)
Best Representation of Chicago in a Chicago-Based Show (2017)
Best Representation of Chicago in a Show Not Entirely Based in Chicago (2017)
Best Resolution to an Eradication of a Commissioned Mural With a Single 311 Call (2018)
Best resurfaced 1970s Chicago-shot black detective TV movie (2019)
Best retrospective exhibition of a Chicago artist in the last year (2015) 
Best revitalized old guard art space (2013)
Best revival of a once great art writing platform (2016)
*Best Riccardo Muti moment at the CSO (2010)
Best rise of the undead (2008)
Best RIP event (2014)
*Best rock album by a Chicago artist in the last year or so (2002)
*Best rock club (2011)
Best Rock-It Out of 1993 (2018) 
“Best rock or pop album by a Chicago artist (in the last year or so) (2008)
Best rock performance/charity fundraiser fusion idea (2015) 
*Best rooftop bar (2009)
Best Russian literature class (2012)
Best SAIC collection at The Walk (2014)
Best saved cultural archive (2019)
*Best scenario for a future Joe (“Drinking Buddies”) Swanberg film (2014)
Best sculpture by a painter (2013)
Best sculpture in a garden (2012)
*Best Second City personality of the last fifty years (2009)
Best second coming of HAL (2008)
Best semi-monthly, under-the-radar, cabaret-esque performance you stumbled into (2019)
Best Sex-Positive Dance to Become a Chicago Institution (2017)
Best shout-out to the Black Power poet Amiri Baraka at EXPO Chicago (2012)
*Best show ever at the Metro (2007)
Best show in a parking lot (2015) 
Best simulacrum (2013)
Best sixties performance art collective revival (2016)
Best smallest bar (2013)
Best SNL Chicago comedian grab (2012)
Best social media manager with the fastest response time (2014)
Best Socially Conscious Small Press Publisher (2017)
Best solo art show (in the last year or so) (2011)
Best song that transcended into a 2016 anthem (2016)
Best sound art (2013)
Best source for jazz concert listings (2013)
Best South Side artist lecture series (2015)
Best Speakeasy-Themed Cabaret-Burlesque Club (2017)
Best splash made by a local press in the last year (2013)
Best sports bar named after an Irish playwright who wrote in English as well as French (2011)
Best Spring Fashion Event (2018)
Best stage reboot (2012)
*Best standup comedy club (2014)
Best stand-up comedy, Leader of Culture (2015) 
Best standup night (2015)
Best Start to Honoring the Legacy of Urban Sculptor Milton Mizenburg, Jr. (2018) 
Best Stogie Store (2017)
Best street art delivery service (2010)
Best street crew igniting an international dance craze (2016)
Best street party (2015)
Best stretch of street art (2015)
Best summer neighborhood arts fest (2014)
Best summer outdoor film screenings (2015)
Best Summer Weeknight Out (2018) 
Best Sunday Night Weekly Music Event (2017)
Best tape label (2019)
Best teen writing incubator (2016)
Best theater dedicated to mental health (2019)
*Best theater production (in the last year or so) (2002)
*Best theater production (in the last year or so) (2007)
*Best theater production (in the last year or so) (2008)
*Best theater production (in the last year or so) (2009)
*Best theater production (in the last year or so) (2010)
*Best theater production in the last year or so (2011)
*Best theater production in the last year or so (2012)
*Best theater production in the last year or so (2013)
*Best theater production (in the last year or so) (2014)
Best theater for everyone, Leader of Culture (2015)
*Best new theater space (opened in the last year or so) (2002)
Best theater for legroom (2019)
Best theatrical cameo (2012)
Best theatrical illness (2013)
*Best thing about the Art Institute’s new Modern Wing (2009)
*Best thing about Tony Tasset’s “Eye” sculpture (2010)
Best tied house (2008)
Best Thing to Happen to Rahm in a Long Time (2017)
Best time to get into the Green Mill for free (2013)
Best time that Chicago’s art scene stormed New York (2014)
*Best title for a future Fall Out Boy record (2007)
*Best title for a future Kanye West record (2007)
*Best title for the next album by R. Kelly (2002)
Best T/QPOC dancer (2016)
Best trained animal spectacle (2016)
Best Trans Memorial Art Exhibit (2017)
Best tribute show that’s actually a play (2013)
Best Tumblr dedicated to semi-sarcastic Chicago-specific GIFs (2012)
Best Turnkey Handover of an Eleven-Year-Old Record Store (2017)
*Best TV series currently or recently set in Chicago (2011)
*Best TV show or movie filmed at Chicago Cinespace (2014)
Best TV show set in Chicago that actually filmed here (2011)
Best tweeting by an art personality (2011)
*Best tweeting by local arts and culture personality (2009)
Best twenty-four-hour performing-arts event (2013)
Best tyrannosaurus rex on Twitter (2019)
Best under-the-radar-but-still-toiling-away playwright (2010)
Best underground gallery (2009)
Best underground press (2007)
Best underrated late-night dance party (2008)
Best underrated museum (2014)
Best underplayed world premiere (2015)
Best unexpected exhibition in an unexpected museum (2011)
Best unexpected, off-the-radar, out-of-nowhere music festival where an Outkast reunion would have been fully appreciated (2014)
Best unexpected piano soloist (2010)
Best unexpected place to see Chicago artists (2013)
Best unexpected place to see contemporary art (2010)
Best unexpectedly touching eulogy (2009)
Best unknown party space in a bar (2008)
Best Unneeded Excuse for Another Dope Rooftop Bar (2018) 
Best urban ritualist (2016)
Best Use of a Robotic Surgical Instrument as Performance Art (2017)
Best use of a washboard (2008)
Best use of abandoned property (2009)
Best use of AstroTurf by a museum (2013)
Best Use of Dance as Political Protest (2017)
Best use of Lil’ Wayne and Rick Ross in art (2012)
Best use of social networking as a movement (2016)
Best venue launch (in the last year or so) (2009)
Best venue to watch a mosh pit without having to be in one (2013)
Best vintage TV show filmed in Chicago (2010)
Best visual storytelling experience (2015)
Best visiting artist (2015)
Best Visiting International Performance Art Performance (2017)
Best viral form of mad cow disease (2007)
Best water fountain (2012)
Best way to blow five bucks and laugh about it (2010)
Best way to dance your way into the week (2015)
Best way to disband a performance company (2008)
Best way to experience a band in person that you will most likely never, ever, ever, never get to see play live. Ever. (2011)
Best way to get trashed and see a show at the same time and have it be appropriate (2011)
Best way to keep the memory of Terry Adkins’ work alive (2014)
Best way to know what’s going on in the underground (2016)
Best way to see new movies cheap, even on a Saturday night (2012)
Best way to seem way more sinister than simply refusing art handlers’ unionization (2014)
Best Way to Walk through the Loop in Winter without Freezing your Arse off (2018)
Best weekly free show for almost two decades (2019)
Best weekly jazz jam (2015)
Best weekly live magazine (2015)
Best weekly performance program (2016)
*Best whiskey bar (2013)
Best windowless no-frills neighborhood bar with cheap Cosmopolitans (2010)
Best witty use of live video projection (2014)
Best “Work of Art: The Next Great Artist” contestant from Chicago (2011)
Best world takeover by a local comics artist (2015)
Best Write Club contender (2015)
Best Writers for Changing the World, An Essay (2016)
Best WWE-influenced feminist spectacle (2014)
Best zine scene (2011)
Best 150th anniversary exhibition (2015)
Made in Chicago: Best bar movement invented in Chicago (2019)
Made in Chicago: Best Chicago-born nineties street dance to make an international comeback (2019)
Made in Chicago: Best dance movement invented in Chicago (2019)
Made in Chicago: Best Ferris wheel in the town that invented Ferris wheels (2019)
Made in Chicago: Best first for film criticism other than Roger Ebert (2019)
Made in Chicago: Best homemade crossover act (2019)
Made in Chicago: Best made-in-Chicago party experience (2019)
Made in Chicago: Best music movement invented in Chicago (2019)
Made in Chicago: Best place to take an out-of-town guest (2019)
Made in Chicago: Best rock ‘n’ roll legacy of a non-rock genre (2019)
Made in Chicago: Best storefront opera company (2019)

FOOD & DRINK

Best of the Best: Al’s #1 Italian Beef (2002)
Best of the Best: Aruns (2002)
Best of the Best: The Berghoff (2002)
Best of the Best: Billy Goat (2002)
Best of the Best: Blackbird (2002)
Best of the Best: Charlie Trotter (2002)
Best of the Best: Foodlife (2002)
Best of the Best: Frontera Grill (2002)
Best of the Best: Harold’s Chicken Shack (2002)
Best of the Best: Irazu (2002)
Best of the Best: La Pasadita (2002)
Best of the Best: Lem’s Bar-B-Q House (2002)
Best of the Best: Leo’s Lunchroom (2002)
Best of the Best: Lula Cafe (2002)
Best of the Best: Manny’s (2002)
Best of the Best: Margie’s Candies (2002)
Best of the Best: Mario’s Italian Lemonade (2002)
Best of the Best: Maxwell Street Polish (2002)
Best of the Best: Pizzerias Uno and Due (2002)
Best of the Best: Pompeii Bakery (2002)
Best of the Best: Superdawg (2002)
Best of the Best: Tru (2002)
Best of the Best: Vienna Beef (2002)
Best of the Best: Wiener Circle (2002)
Best Adult Slushie for Any Weather Conditions (2018)
Best after-work buffet (2009)
Best airport food (2002)
Best alcohol to trick your friends into drinking (2011)
*Best al fresco dining (2013)
Best all-you-can-eat sushi buffet (2012)
Best Alpine inn in the shadow of Parson’s Chicken & Fish (2019)
Best Amaro cocktails menu (2012)
Best American culinary discovery(2007)
Best Amerindian-African food (2009)
Best (and perhaps only) surviving place to eat featured in “The Blues Brothers” (2015)
Best-anticipated German restaurant opening (2012)
Best argument that Chicago is a great food town(2007)
Best Argentinean food (2012)
Best artisan-inspired donut spot (2019)
*Best authentic martini (2002)
Best award of Michelin stars (2010)
Best bakery tortes (2008)
Best ballpark dog (2002)
*Best banh mi (2010)
Best Bar for Trippy Cocktails (2017)
Best bar snack (2013)
Best bar that makes you feel in control of your drinking (2016)
Best Bar to Drink for a Cause (2017)
*Best bar to drink with tourists (2014)
Best Bar to Escape Football Season (2018)
*Best barbecue (2010)
Best Beachside Bar (2017)
Best beer festival (2011)
Best beer hall for an après-dinner spanking (2016)
Best Beijing (formerly Peking) duck service (2008)
Best Berlin-style sour beer (2012)
Best birrieria (2008)
*Best Bloody Mary (2002)
*Best bloody mary (2007)
Best boozy dessert (2013)
Best borscht (2010)
Best bottled cocktail (2013)
Best Boulevardization of Boul Mich (2018)
*Best bourbon selection (2014)
Best brains in Chicago (2010)
Best breadsticks (2007)
Best breakfast alternative to the wait at Cozy Corner (2009)
Best breakfast/lunch spot in a flower shop (2009)
Best breakfast spot for late risers (2012)
Best Brewery Kitchen (2018)
Best broccoli rabe (2010)
*Best brunch (2002)
*Best brunch (2007)
*Best brunch (2012)
Best brunch (non-frou-frou division) (2011)
*Best bubble tea (2008)
*Best Buffalo wings (2009)
Best burgeoning neighborhood to have a beer… or two… or ten (2019)
*Best burgers (2009)
*Best burgers (2014)
Best café for coffee and respect (2008)
Best café for sprawling out (2008)
Best cafe to experience a scene out of “Portlandia” (They can pickle that!) (2013)
Best cafe with a deceptively Russian name (2012)
Best caffeinated pastry (2015) 
*Best Cajun/New Orleans-style restaurant (2008)
Best Camarones a la Diabla (2012)
Best Candy Store (2017)
Best Caribbean-style fish (2012)
Best case for kale (2015) 
Best caviar and ice cream combo (2013)
Best ceviche paired with alt-pop rarely played in Peru (2016)
Best chai (2012)
Best “changing of the guard” in the restaurant world (2012)
Best cheap classy pizza and beer special (2014)
Best cheap eats feast in Chinatown (2015) 
Best cheap Mexican food (2011)
Best cheese curds (2015) 
Best chebapi plate (2014)
Best cheese sandwich (2011)
Best chef blogger (2009)
Best “Chicago” tamales (2010)
Best Chicago-themed restaurant on the North Side (2011)
*Best chicken (2013)
Best chicken sandwich (2007)
*Best chicken Vesuvio (2008)
*Best chili (2009)
Best chili dog (2007)
Best Cinema In-House Restaurant (2017)
Best classic nachos, Leader of Culture (2015)
Best cocktails for the indecisive (2013)
Best coffee alternative (2015)
Best Coffee Flights (2017)
Best coffee shop for a writer, Leader of Culture (2015)
Best Coffee Shop for Dog-Watching (2017)
Best coffee shop to distract you from working (2016)
Best “Cold Brew” (2017)
Best Cold-Weather Comfort Food Dish (2018)
Best collegiate cookbook (2011)
Best contemporary take on the Swedish bakery (2019)
Best contribution to the smell of Chicago (2013)
Best Cookbook After a Twenty-Year Wait (2017)
Best Costa Rican restaurant (2012)
Best crackers (2013)
Best craft honey (2014)
Best Chicago craft cupcake maker (2014)
Best cranberry borscht (2011)
Best Cranberry Guacamole (2017)
*Best croissant (2013)
Best Croquetas North of Miami (2017)
Best crowd-sourced local brewery (2011)
*Best Cuban sandwich (2008)
Best Cubano (2012)
Best culinary tours (2011)
Best cup of tea (2013)
Best cupcake from a vending machine (2012)
Best cupcake tours (2011)
*Best cupcakes (2011)
Best cured meat (2013)
Best damn muffins ever (2015)
Best deal on cheesecake in Chicago (2016)
Best Deals on Really Ripe Produce (2017)
*Best deli (2010)
Best designer cake shop (2008)
Best dessert platter (2014)
Best diner to take an uncomfortable suburbanite (2013)
Best dish that most closely resembles your grandma’s secret stuffing (2008)
Best dive-bar burger time capsule (2013)
Best dive bar with gourmet grub (2008)
Best downtown cafeteria (2010)
Best drag shows in Oak Park (2019)
Best-dressed Irish bar owner (2012)
Best drive-in for really good soggy, limp French fries (2016)
Best duck in Chicago (2019)
Best Earth Day celebration (2011)
*Best egg rolls (2014)
Best el pastor taco, Leader of Culture (2015)
*Best empanada (2009)
*Best Ethiopian restaurant (2007)
*Best Ethiopian restaurant (2012)
Best Evidence That Chicago Is The Sultan of Speakeasies, An Essay (2016)
Best Example Of Dragging A Kicking-Screaming Frank Lloyd Wright Into Twenty-First Century Chicago (2017)
Best fake reason Laurent Gras left Lettuce Entertain You’s L20 after it was awarded three stars (2010)
*Best falafel (2007)
*Best falafel (2012)
Best falafel in a jewelry store (2019)
Best Fall Fest for Foodies Who Can’t Afford Chicago Gourmet (2018) 
Best Fancy Pants Ukrainian Restaurant (2017)
Best faux Asian dish (2015) 
Best festival pastry treat (2014)
Best fifth-quarter fast food (2016)
Best Filipino breakfast (2010)
Best Filipino pop-up (2016)
Best fine dining in the South Loop (2019)
*Best fish & chips (2007)
*Best fish and chips (2012)
*Best fish tacos (2010)
Best Flinstonian roast meat presentation (2012)
Best focaccia bread (2012)
*Best foie gras, now that it’s legal again (2008)
*Best food at Taste of Chicago (2002)
Best food business move of the year (2010)
*Best food truck (2010)
*Best food station at Eataly (2014)
Best former bartender with a chance to reach Charles Joly heights (2016)
Best 4am pizza delivery (2013)
*Best french fries (2011)
Best French fry substitute (2014)
Best French toast (2009)
Best Fresh and Quick Sushi West of The River (2017)
Best fresh bread (2015)
*Best fried chicken (2008)
Best Fried Chicken That Might Make You Wanna Skip Harold’s (2017)
Best fried meat (2013)
*Best fried shrimp (2008)
Best fried vegetables (2013)
*Best frozen cocktail (2008)
Best Gangster Brewery Destination Distillery (2018)
Best Garrett Popcorn TV Shoutout (2017)
*Best gastropub, whether or not it calls itself a gastropub (2007)
Best Gift for Your New York Friend at Holiday Time (2018) 
Best gin & tonic (2013)
Best gizzards you’ve ever eaten (2019)
Best gourmet Asian (2012)
*Best gourmet carryout (2009)
*Best gourmet carryout (2014)
*Best gourmet doughnut shop (2012)
Best granitas (2009)
*Best Greek restaurant (2011)
Best grilling rub recipe (2011)
Best grocery store (2007)
Best gross-out original Chicago treat (2019)
*Best guacamole (2002)
*Best guacamole (2007)
*Best guess on what next media stunt the artist formerly known as Graham Elliot Bowles will employ to promote his burgeoning TV and restaurant empire? (2010)
Best hamburger empire based in Chicago besides McDonalds (2009)
Best handcrafted non-alcoholic drinks (2011)
Best Hawaiian lunch spot (2011)
Best hidden cafe/juice bar (2016)
*Best high-end chef serving low-end food (2010)
Best high tea (2010)
Best holiday potluck dish (2011)
Best hole-in-the-wall smoke shack, Leader of Culture (2015)
Best Hot Chocolate in Winter—and Summer (2018) 
Best hotdog shack (2008)
Best House Chips (2017)
*Best house-made charcuterie (2009)
Best house-made radler (2014)
Best hummus (2013)
Best hummus alternative (2013)
Best humungous margaritas (2011)
Best Ice Cream on a Hot Summer Day (2018)
Best iced coffee that’s not cold brew but rather superior espresso + spicy ganache (2016)
*Best imaginary Twitter post by Herman Joseph Berghoff (2009)
Best impulse cash-register buy (2014)
Best Indian buffet (2012)
*Best Indian restaurant (2009)
Best Indonesian food (2012)
Best inducement to visit all the restaurants you ever meant to (2019)
Best Injera bread (2012)
Best in-house flour mill bakery (2015)
Best Instagrammable brunch (2016)
Best “It’s Almost Swimsuit Season” Spot (2018)
*Best Italian beef sandwich (2011)
Best Italian breakfast (2012)
Best Italian ice place outside of Little Italy (2016)
Best Italian Place for Carbonara (2017)
Best Italian-Polish fusion food in Chicago (2019)
Best Jewish deli inside an Italian pharmacy, Leader of Culture (2015) 
Best juice (2013)
Best kept bartender secret (2014)
Best Korean BBQ Tacos (2017)
Best Kyrgyz Food in Chicago (2017)
Best lard-fried pork in Chicago (2019)
Best Last-Rites-Read, Bucket List, Final-Bite-in-Life, Single-Dish, Comfort Food (2018)
Best late-night industry darling (2013)
Best latte art (2010)
Best Lithuanian bakery (2011)
Best lentil soup (2015)
Best local bbq sauce (2010)
*Best local food blog (2009)
Best Local Food System on the West Side (2018)
Best Local Franchise Public Implosion (2017)
Best local jam (2012)
*Best local spirit/liquor (2010)
Best Local Squeaking Onto Another Best-Bars-In-The-World List (2018)
Best locally brewed beer (2008)
Best lunch for the thrifty and hungry (2016)
Best lunchtime fish special (2009)
*Best macaron (2010)
Best mango lassi knockoff (2016)
Best manifestation of Chicago’s food-production future (2016)
Best marinade (2014)
Best masochistic move by a local chef (2010)
*Best meatball sandwich (2010)
Best meatless tzimmes (2011)
Best meatloaf sandwich (2008)
Best menus (2014)
*Best metaphor that describes your feelings the day Hot Doug’s closed (2014)
*Best Mexican restaurant (2011)
Best Mexican restaurant open at 3am (and later) (2014)
Best Mezcal Bar (2017)
*Best Middle Eastern restaurant (2010)
Best mignardise (2013)
*Best milkshake (2011)
Best mimosa deal for getting drunk before noon (2013)
Best mochi (2013)
*Best mojitos (2002)
*Best mojitos (2007)
Best Montreal-style poutine in Chicago (2009)
Best Moroccan (2012)
Best Moroccan recipe on a Chicago food website (2012)
Best museum-worthy cupcakes (2010)
Best mussels (2011)
Best neighborhood for urban foraging (2015)
Best never-before-revealed reasons why the Publican restaurant (from the Blackbird and Avec team) took so long to open (2008)
Best new Al Capone shrine (2007)
Best new brewery (2011)
*Best new chef (2009)
Best New Chicago Food Book That Can Never Be Completed (2017)
Best New Club (2017)
Best new craft foodie idea (2014)
Best new falafel sandwich bar (2009)
Best New Fall Happy Hour (2018) 
Best New Fancy Restaurant Selling Street Food (2017)
Best new fatty food trend (2011)
Best New Food District Branding (2017)
Best new innovative beverage idea (2014)
Best new Japanese fusion restaurant that’s not L20 (2008)
Best new Middle Eastern restaurant (2008)
Best new neighborhood brewery and restaurant (2012)
Best new one-two punch (2015) 
Best new pancake house (2008)
Best New Restaurant in the Northern Suburbs (2017)
*Best new restaurant (opened in the last year or so) (2002)
*Best new restaurant (opened in the last year or so) (2007)
*Best new restaurant (opened in the last year or so) (2008)
*Best new restaurant (opened in the last year or so) (2009)
*Best new restaurant (opened in the last year or so) (2010)
*Best new restaurant (opened in the last year or so) (2011)
*Best new restaurant opened in the last year or so (2012)
*Best new restaurant opened in the last year or so (2013)
Best new restaurant (opened in the last year or so) (2014)
Best new restaurant that was a pop-up (2019)
Best new South Side restaurant to earn a Michelin Bib Gourmand award (2010)
Best new stir-shake-sip guide (2016)
Best New Way to Eat Ice Cream (2018)
Best New West Loop Lunch (2017)
Best New WTF, WYKAT (“What You Know About This?”) Speakeasy in the City (2017)
*Best newish Hyde Park resto (2014)
Best Next “It” Bar (2018)
Best of the new steakhouses (2010)
Best “next” Alinea (2016)
Best nightclub trend we’d like to see catch on (2007)
Best $9 curry braised duck, pickled cauliflower and mint chutney yogurt on baguette at a BYOB (2011)
Best non-bbq rib (2009)
Best non-Italian spaghetti (2015)
Best non-traditional horchata (2012)
Best Non-Two-Hour Wait for Boozy Slushies (2017)
*Best noodles (2009)
Best North Side Place for South Side Specialties (2017)
Best Nostalgia Ice Cream Shop (2018)
Best octopus (2014)
Best old school cafeteria-style Chicago restaurant in the Loop (2016)
Best old-timey Chicago restaurant that isn’t The Berghoff (2019)
Best Old-Timey First-Date Spot (2017)
*Best option for fancy hotdogs now that Hot Doug’s has closed (2014)
Best outdoor lunch (2002)
Best outdoor patio serving Middle Eastern food (2015)
Best overall deal, Leader of Culture (2015)
Best overpriced coffee that’s actually worth it (2016)
*Best oysters (2014)
Best paleta (2015)
*Best pancakes (2010)
Best panna cotta (2014)
Best Pastrami Outside Brooklyn (2017)
Best panzanella salad twist (2008)
Best Paris Brest (2014)
Best pasta dish (2009)
Best pasticceria for pasta made under the direction of an Italian pastamatrix (2019)
Best pastillas (2012)
*Best pastries (2009)
*Best pastries (2014)
*Best pastry chef (2013)
Best peach cobbler (2010)
Best Persian restaurant (2010)
*Best Peruvian restaurant (2013)
Best Philly cheesesteak (2013)
Best Picnic Date Destination (2017)
Best pistachio gelato (2015)
Best Pita Inn Spinoff (2017)
*Best pizza (2011)
Best pizza made by a man who can’t let go of penises (2016)
Best pizza place for ghastly late-night madness and existentialism (2012)
Best pizza served in a non-delivery/not strictly Italian restaurant (2012)
Best place for a bowl of vegan chili and a show (2014)
Best place for an inexpensive lunch of unadulterated food in the North Michigan Avenue area if you a re tired and hungry after gazing in the windows at Chanel or pondering the latest conundrums at the MCA but don’t want to go to a food court or an expensive restaurant (2010)
Best place for a bowl of meaty chili and a show (2014)
Best place for an after-dinner spanking (2019)
Best Place for an Everlasting Summer Patio Vibe (2018)
Best place for a midnight grilled cheese (2015)
Best place for a special meal, Leader of Culture (2015)
Best Place for Burgers (If You Tried to Go to Au Cheval and There Was a Three-Hour Wait) (2017)
Best place for brains and a nice chianti (2019)
*Best place for craft cocktails (2007)
*Best place for craft cocktails (2012)
*Best place for dessert (2008)
*Best place for dessert (2013)
Best place for fast food with a side order of social guilt (2013)
Best place for high-rise dwellers to emulate the backyard barbecue, any time of year (2007)
Best place for inexpensive French toast (2010)
Best place for Mayor McCheese to commandeer on Foursquare if McDonald’s fired him (2010)
Best place for wholesale tofu (2011)
Best place to avoid Cubs fans in Wrigleyville (2019)
Best Place to Barbecue in Summer (2018)
Best Place to Bring Very Young or Old People for Christmas Dinners (2018)
Best place to bring your in-town friends who want anything but deep dish pizza (2019)
Best place to bring your out-of-town relatives who just want to eat deep dish pizza (2019)
Best place to buy Lechon in a trailer (2009)
Best place to buy Russian buckwheat, ginger cookies and kvass (2012)
Best place to chow down and learn tango (2019)
Best place to drink a Thanksgiving cocktail (2016)
*Best place to drink bourbon (2009)
Best place to drink caipirinha (2012)
Best place to drink coffee like a travel agent from the sixties (2019)
Best place to drink lager from ye olden days (2016)
Best Place to Drink to the Changing Season (2018)
Best place to eat and drink with boorish acquaintances (2016)
Best place to eat Brazilian appetizers (2012)
Best place to eat brick (2007)
Best place to eat croissants and read (2016)
Best place to eat cured fish (2016)
Best place to eat, drink, and party in a traditional-but-relaxed place with excellent food close to Chicago, thus immune to Hizzoner’s threatened smoking ban (2002)
Best Place to Eat German Food and Wear your Lederhosen in Winter (2018)
Best place to eat head cheese (2009)
Best place to eat paella (2019)
Best Place to Eat So-So Barbecue (2018) 
Best place to eat specialized primary lymphoid organs (2016)
Best place to enjoy a Mother-in-Law (2019)
Best Place to Enjoy the Georgian National Dish (2018)
Best Place to Feed Your Inner Child with Adult Portions (2017)
Best Place to Feel Tropical in a Snowstorm (2018)
Best place to float your tamale boat (2019)
Best place to get a decent meal after midnight (2010)
Best place to get dripped on by an errant a/c unit (2013)
*Best place to get a salad (2008)
Best place to get red caviar (2012)
Best Place to Get Specials from Leo’s Lunchroom (RIP) (2017)
Best place to get your bag lunch (2012)
Best place to get your ghostbusters on (2016)
*Best place to get your picnic (2007)
Best place to give back to the community without even trying, Leader of Culture (2015)
Best place to go after a gallery opening that’s not Perez (2013)
Best Place to Have a Band Meeting (2018)
Best Place to Have a Beer and Save Democracy (2018) 
Best Place to Have a Beer While Reading a Book (2017)
Best Place to Have a Heart (2017)
Best place to have dinner and a dance party (2015)
Best Place to Have Lunch on Someone Else’s Dime (2018)
Best Place to Have Rattlesnake for Dinner (2017)
Best Place to Hide Out From the Cold (2018) 
Best place to incite home envy while dining (2016)
Best place to keep kosher for lunch (2007)
Best Place to Listen to Cumbia and Eat Meat in Its Own Juice (2017)
Best place to lose yourself (2013)
Best place to meet strangers over breakfast (2008)
Best Place to Order a Whole Animal (Alligator, Wild Boar, Goat, etc.) (2017)
Best place to practice your French outside the classroom (2016)
Best place to satisfy your Middle Eastern dessert craving (2016)
Best place to sit outside and eat nachos (2007)
Best place to sneak in a quick hot dog after work (2019)
Best Place to Source Rare Ingredients (2017)
Best Place to Stock Up on Ecuadorian Dry Goods (2017)
Best place to stock up on fruits and nuts (2008)
Best place to take a date with whom you hope to grow old (2015)
Best place to taste the rainbow when you’ve outgrown Skittles (2019)
Best place to tip the barista by gratuitously exercising your First Amendment rights (2012)
Best place to try the most popular Russian cake named after a French Emperor (Napoleon) (2012)
Best place to try the national food of the former Kirghiz Soviet Socialist Republic (now Kyrgyzstan) (2012)
Best place to try the national food of the former Uzbek Soviet Socialist Republic (now Uzbekistan) (2012)
Best Place to Wake up in Springtime and Smell the Bacon (2018) 
Best Place You Haven’t Considered Visiting, But Really Should (2018)
Best place your taxi driver ever took you (2016)
Best Places That Proved and Prove Chicago Is More than a “Hog Butcher”, An Essay (2016)
Best pop-up artisanal food experience (2015)
*Best pork belly (2008)
Best Possible Place for an Impossible Burger (2019)
Best Post-Drinking Meal at 2am under $10 (2018) 
Best prix-fixe lunch deal, Leader of Culture (2015)
Best prix fixé menu-quality dish not served in a prix fixé (2012)
Best proof that it’s not the bar, it’s the barkeep (2015) 
Best prosciutto lollipop (2009)
Best putdown from one liquor to another (2013)
Best quote from a local chef (2010)
Best Rainbow Toast (2017)
*Best ramen (2014)
Best raw vegan pastries (2010)
Best real fried chicken shack now that it’s hip (2015) 
Best reason Dominick’s won’t be missed too much (2013)
Best reason for breakfast (2011)
Best reason to avoid the long lines at Xoco (2009)
Best reason to choose tofu over pork (2009)
Best reason to employ a personal cardiologist (2012)
Best reason to indulge in a 1980s restaurant cliché (2009)
Best Reason to Leave Rogers Park or Hyde Park for Vegan Food (2018) 
Best reason to start drinking soda again (2019)
Best reason to stop teasing vegetarians and become one (2009)
Best reason to visit the Garfield Park Conservatory (2007)
Best recently shuttered restaurant, Leader of Culture (2015) 
Best regional dinner series (2009)
Best reimagined nachos, Leader of Culture (2015)
Best reopening of an old favorite (2015)
Best restaurant bathroom (2015)
Best restaurant disaster and recovery (2009)
Best restaurant ever, Leader of Culture (2015)
*Best restaurant for a holiday meal if mom’s on a cruise (2010)
Best restaurant for fine dining for the most reasonable prices (2019)
Best restaurant for talking, Leader of Culture (2015)
Best restaurant for zero-proof cocktails (2019)
Best restaurant in the back of a supermercado (2010)
Best restaurant named after an extinct animal (2007)
Best restaurant near the Art Institute (2002)
Best restaurant street for a diverse palate, Leader of Culture (2015)
Best restaurant to buy art (2016)
Best restaurant to have the most expensive egg in Chicago (2016)
Best restaurant to inspire a road trip (2016)
*Best restaurant to pop the question (2007)
Best restaurant to teach your kids Spanish (2016)
Best restaurant to wait for your table (2007)
Best restaurant with a chalkboard menu (2008)
Best Return of the Native, Booze Dept. (2018) 
Best rock ‘n’ roll-inspired restaurant (2014)
Best Roman-style pizza (2012)
Best rotisserie chicken (2007)
Best salad (2013)
Best salad bar in a Brazilian steakhouse (2012)
Best salad in a jar (2016)
Best salumeria (2012)
Best sandwich in cookie form (2016)
*Best sandwich shop (2012)
Best sangria (2002)
*Best sangria (2007)
Best sangria deal (2007)
Best savory cookie (2014)
Best savory dessert (2014)
Best savory, um sweet… no, savory dessert (2015)
Best savory waffle (2011)
Best Scandinavian Restaurant That Really Isn’t Scandinavian (2017)
*Best seafood restaurant (2008)
Best Seasonal Donut Shop (2018) 
Best secret breakfast at a dive bar (2016)
Best “secret” home food pop-up (2019)
*Best service story in a restaurant (by “best” we mean the story, not the experience) (2014)
Best Single Dish to Make Someone Not from Chicago Understand Why We Are, as Bon Appétit Claimed, the “Restaurant City of the Year” (2017)
Best slice of the United Kingdom (2014)
Best smelling food truck (2011)
Best soft serve in Chicago (2016)
Best source for dirty jokes with your dessert (2016)
Best South Side Mexican Restaurant with vegetarian options (2012)
Best South Side spot for convenience food (2014)
Best Speakeasy (2017)
Best spicy drink that’s not a Bloody Mary (2013)
Best spot for smoked shrimp (2019)
Best Self-Description That Shows That 1970s Chicago Will Be Here So Long As Lettuce Entertain You Enterprises Is (2018)
Best Source for Summer Barbecue Meat (2018) 
Best spinach pie (2010)
Best Steve Dolinsky television moment proving he’s not just another pretty food journalist with a shiny 8” x 10” headshot (2008)
Best sticky toffee pudding (2012)
Best Street Food You Just Don’t See Anymore (2017)
*Best sub sandwiches (2002)
*Best sub sandwiches (2007)
Best Summer Date Night Restaurant (2018) 
Best “Summer is Finally Here and So Worth It” Spot (2018) 
Best Sunday comfort food (2010)
Best surprising street-food recommendation (2016)
*Best sushi (2013)
Best sushi in an airport Champagne bqr (2012)
Best sushi in the Loop (2007)
Best Sweater-Weather Guilty Pleasure (2018) 
Best Swedish breakfast (2011)
*Best Swedish restaurant (2007)
Best sweet use of horseradish (2011)
*Best taco from a non-traditional taqueria (2010)
*Best tacos (2013)
Best tamale food truck (2012)
Best tamale in the world (2015) 
Best tamale not served from a red cooler (2012)
Best taqueria for taste-bud-obliterating chilies (2016)
Best-tasting bread for the Russian palate (2012)
*Best tasting menu (2013)
Best Tex-Mex food, i.e. not Rick Bayless or organ-meat-serving, regional-taqueria-skewing Mexican food (2008)
Best Thai dish (2012)
Best Thai food and toy museum combo (2012)
*Best Thai restaurant (2011)
*Best thing you’ve eaten recently that filled you with the most shame (2014)
*Best thing you’ve eaten recently that made you stop and think, “This might be the best I’ve ever eaten” (2014)
Best Tiki Drinks (2017)
Best time-tested pizza parlor (2010)
Best timeless restaurant, Leader of Culture (2015)
Best tiny birthday cakes sold at a Thai restaurant (2011)
Best traditional neighborhood bakery with a contemporary twist (2011)
Best trip to Algiers without leaving Andersonville (2011)
Best turkey club (2007)
Best Turkish restaurant (2010)
*Best tweeting by a local food personality (2009)
Best Ukrainian/Russian Deli South of the Suburbs (2017)
Best underground dinner (2013)
Best underground supper club (2011)
Best Underground Oyster Bar (2017)
Best under-the-radar Italian restaurant (2010)
Best under-the-radar Mexican (2012)
Best unkept bartender secret (2014)
Best unlicensed street food (2015)
Best unusual food item (2002)
Best use of avocado (2014)
Best Use of Chambord In Chicago (2017)
Best use of chicken skin (2012)
Best use of eighties kitsch (2010)
Best Use of Onions to Make Your Pizza Taste Like Fall (2018) 
Best use of smoke (2013)
Best use of Speculoos (2012)
Best use of tofu (2010)
Best vegan cafe connected to a production space (2013)
Best vegan cookie (2013)
Best Vegan Korean restaurant (2012)
Best vegan restaurant (2011)
*Best vegetarian restaurant (2011)
Best view from a bar in Chicago (2019)
Best Wagyu steak salad (2009)
Best waiter in a pizzeria (2012)
Best waiting-for-a-restaurant bar (2016)
Best way to deal with annual problems of persistently long lines and lack of food at Chicago Gourmet (2010)
Best way to deliver a restaurant check so the customer forgets it’s actually a bill (2011)
Best way to drink squash (2015)
Best Way to Get a Good Poke at Home (2017)
Best way to keep an even buzz on a night of drinking, Leader of Culture (2015)
Best Way to Know For Sure that Spring has Sprung (2018)
Best wine blog (2011)
Best wine list few people know about (2010)
Best Winter Outdoor Fireplace Bar (2018)
Best Wisconsin Bar Outside of Wisconsin (2017)
Best 1940s drive-in other than Superdawg (2015)
Made in Chicago: Best Chicago-born condiment for perking up a boring sandwich (2019)
Made in Chicago: Best Chicago-born Puerto Rican sandwich (2019)
Made in Chicago: Best contribution to the barbecue arts (2019)
Made in Chicago: Best food stand to get three signature Chicago foods (2019)
Made in Chicago: Best homegrown awards show (2019)
Made in Chicago: Best riff on Mediterranean cuisine other than Chicago-style pizza (2019)

GOODS & SERVICES

Best of the Best: Dusty Groove America (2002)
Best of the Best: El train (2002)
Best of the Best: Facets Multimedia (2002)
Best of the Best: Marshall Field’s State Street (2002)
Best of the Best: Paulina Meat Market (2002)
Best of the Best: Prairie Avenue Bookstore (2002)
Best of the Best: Quimby’s (2002)
Best of the Best: Salvage One (2002)
Best of the Best: Sam’s Wine Warehouse (2002)
Best of the Best: Seminary Cooperative Bookstore (2002)
Best accessories to dance with (2014)
Best addition to Michigan Avenue (2011)
Best adult playdate (2016)
Best adult toys and novelties you won’t be tempted to put up an orifice (2007)
Best alternative to the post office(2007)
Best American-made Denim (2017)
Best Amish market complete with walk-in refrigerator and fresh poultry (2011)
Best Analogue Apparition (2019)
Best (and cheapest) way to see Chicago during the warmer months (2011)
*Best animal shelter (2011)
*Best antique shop (2009)
*Best antique shop or market (2014)
Best App While Idling Under a Flight Path (2017)
Best architecture and design book store (2014)
*Best art supply store (2011)
Best artisan design shop in Andersonville (2011)
*Best artisan market (2013)
Best Artist Book Guaranteed to Make your Life a Little Brighter (2018)
Best attempt to connect communities (2013)
Best attribute of the massive new 24-hour Dominick’s in West Town (2007)
Best bags to attach to your bike (2015)
Best bakery to buy your own pretzel buns (2010)
Best barbershop not in the movie “Barbershop” (2002)
Best bar alternative (2014)
Best BDSM-supply delivery service (2013)
Best Beatboxer-Vegan Chef (2018) 
Best bicycling revolution not fully espoused by a mayor who claims to be spot-welded to his own two-wheeler (2007)
Best bike repair service (2016)
*Best bike shop (2002)
*Best bike shop (2007)
*Best bike shop (2012)
Best bikini wax (2002)
Best birthday party accessories (2010)
Best bookstore, Leader of Culture (2015) 
Best bookstore to find undoubtedly fascinating cultural texts that you will never read (2014)
Best Bookstores to Guard Over the Culture, An Essay (2016)
Best Boutique Brand to Feel Good Underneath It All (2017)
Best boutique for the stylish male (2015)
Best boutique mascot (2010)
Best breadsticks (2007)
*Best butcher shop (2007)
*Best butcher shop (2012)
Best camera store (2008)
Best cave-to-table concept (2014)
Best chair (2012)
Best chainmaille maker (2014)
Best chance to buy cheap books en masse (2013)
*Best cheap-chic chain in Chicago (2011)
Best cheap downtown bar (2010)
Best cheap haircut (2007)
Best cheap haircut (2014)
Best Chicago Sports Redesign (2018)
Best child play space (2015)
Best Chinese herb shop (2009)
*Best chocolatier (2010)
Best Christian bookstore on the North Side (2010)
Best church for getting your pets blessed (2010)
*Best comic book shop (2012)
*Best comics shop (2007)
Best Chicago Cookbook You Can Actually Cook From (2018) 
Best Co-Op Grocery Expansion (2017)
Best counter-intuitive name for a dental practice (2010)
Best Country Music Radio Station (2018)
Best Creative Community Gathering for Chicago’s Creative Minds (2018) 
Best creative services for local fashion entrepreneurs (2016)
Best crossover craft event (2014)
Best cultural combination in a neighborhood grocery store (2013)
Best custom bikes (2011)
Best custom-made designer boxes (2011)
*Best daily-deals site (2011)
Best design by a craft coffee mug-maker (2014)
Best Dip Powder Manicure (2018) 
Best discount shoe store (2008)
Best doctor when you cannot breathe or hear (2015)
Best dog beach (2019)
Best dollar store (2007)
Best Drums Emporium (2018)
Best dry cleaners with an antique museum inside (2011)
*Best eco-retailer (2008)
Best electronic-cigarette shopping (2013)
Best Emergency Button Store in the Loop (2017)
Best escape from Chicago (2016)
Best ethnic bakeries in neighborhoods you don’t go to (2015)
Best example of DIY creativity gone global (2008)
Best excuse to shop for shoes (2011)
Best facial moment you’ll be thinking about for a month (2011)
Best fall craft fair (2014)
*Best farmers’ market (2010)
Best fashion future boutique (2010)
Best female designers, Leader of Culture (2015)
Best Feminist Lettering Shop and Design Studio (2018)
Best Film Retrospective (2018) 
*Best flower shop (2008)
*Best flower shop (2013)
Best foreign coin exchange (2013)
*Best framing shop (2014)
Best gallery for hand-painted African movie posters (2015)
*Best garden store (2008)
*Best garden store (2013)
Best gear for chicks who love kicks (2011)
Best gift shop in West Town, Leader of Culture (2015)
Best gift shop to bring your friends laughs (2019)
Best gnarling dog restaurant t-shirt (2010)
Best greeting cards for Chicago aficionados (2015) 
*Best grocery store (2007)
*Best grocery store (2012)
Best hairstylist chat (2012)
Best handmade candles (2014)
Best handmade jewelry (2014)
Best handmade soap (2014)
Best handmade undies (2014)
Best handwoven (2014) 
Best Harbinger of Spring in Chicago (2018)
Best Harmonica Hangout (2018)
Best Head Shop (2017)
Best homeless outreach organization (2016)
Best Hoop Dream Turned Reality (2017)
Best hotel with cool decor and affordable rates (2012)
Best humanity-enriching use of a Yelp review (2013)
*Best IKEA feature (2002)
Best Illinois hotel right on Lake Michigan (2019)
*Best imaginary Twitter post by Marshall Field (2009)
Best imported German dirndl dresses (2010)
*Best independent bookstore (2002)
*Best independent bookstore (2007)
*Best independent bookstore (2012)
Best independent bookstore often overlooked (2012)
Best independent escort (2013)
Best Indication That Home Delivery Is Out Of Control (2018) 
Best indie film rental store (2010)
*Best indie record store (2010)
Best infrastructure idea that pretty much worked out the way it was designed to (2016)
Best interior design shop (2015)
*Best iPhone app with Chicago relevance (2009)
Best judgment-free zone (2016)
Best kids birthday party destination (2013)
Best kids shoe store (2013)
Best lampwork-centric glass training and education center (2015)
Best Learn-to-Fish Lessons with a View (2017)
Best Lifestyle Blog to Keep you Inspired On and Offline (2018)
*Best lingerie shop (2013)
*Best liquor store (2010)
Best Lithuanian intellectual auto mechanic (2012)
Best Live Auction Experience (2018) 
Best Live Band Country Karaoke (2017)
Best living legend in the magic world who is Armenian and runs his own magic shop (2011)
Best local athleisure line (2016)
*Best local cemetery (2009)
Best local personal style blogger (2014)
Best local shopping or consumerist blog (2009)
*Best local shopping or consumerist twitterer (2009)
Best local soap company (2011)
Best local tattoo artist who probably will not ink you (2010)
*Best locally made bread (2010)
Best location for a new boutique (2015)
Best magic shop (2011)
Best Magician Who is Not Your Ordinary Magician (2018)
Best Man for a Custom Blade (2017)
Best Man to Walk into Hungry at a Saloon (2018) 
Best Manufacturing Makers Space (2018)
Best marijuana strain (2013)
Best masseuse (2011)
*Best menswear boutique (2008)
*Best menswear boutique (2013)
*Best mobile-phone-service provider (2010)
Best mode of transportation to other, less-interesting midwestern cities (2013)
Best “Movin’ on up” Pop-up (2018)
*Best museum store for jewelry (2008)
Best music school, Leader of Culture (2015)
Best mysterious storefront (2016)
Best neighborhood clothing store, Leader of Culture (2015)
Best neighborhood jeweler (2008)
Best new boutique or shop (opened in the last year or so) (2007)
*Best new boutique (opened in the last year or so) (2008)
*Best new boutique (opened in the last year or so) (2009)
*Best new boutique or shop (opened in the last year or so) (2010)
*Best new boutique or shop opened in the last year or so (2011)
*Best new boutique or shop opened in the last year or so (2012)
Best New Cafe Notion by a Whisker (2017)
*Best new clothing store (opened in the last year or so) (2002)
*Best new boutique opened in the last year or so (2013)
*Best new boutique or shop (opened in the last year or so) (2014)
Best new Chicago-based Facebook group (2016)
Best new coffee shop to write a paper in while listening to good music (2009)
Best new community resource (2019)
Best new fashion line, Leader of Culture (2015)
Best new hotel (2014)
Best new loyalty rewards program (2013)
Best new Old World sauna (2010)
Best new Pilsen vintage store (2013)
Best new permanent home for a Chicago printmaking institution (2015) 
Best new printmaking shop (2014)
Best new retail concept we hope catches on (2007)
Best new sex toy and where to get it (2013)
Best new salon/barbershop (2015)
Best new tabletop RPG gaming shop (2013)
Best new youth-only maker space (2015)
Best Newish Bookstore (2017)
Best ninety-nine-percent-off sale (2019)
Best North Side dog rescue (2013)
Best nonprofit youth center/bike-shop fusion (2015)
Best ongoing vintage market (2012)
Best Paris Web site by a Chicagoan (2009)
*Best pet boutique (2002)
Best pet boutique (2010)
Best pet-pampering salon in Logan Square (2013)
Best Place for an Outdoor Swim in Winter (2018)
Best place for discount home goods (2008)
Best place for fresh meat for pets (2010)
Best place for kids to have fun with science, Leader of Culture (2015) 
*Best place for kitchen gadgets (2013)
Best place for matched, and mismatched, juice and drinking glasses (2011)
Best place to “Be Like Mike” (2016)
Best place to become an urban cowboy (2012)
Best place to be when you’re having a sudden wardrobe crisis (2014)
Best Place to Bulk Up or Slim Down (2018)
Best place to buy beads (2007)
Best place to buy Brazilian music (2012)
*Best place to buy cheese (2002)
*Best place to buy coffee beans (2010)
*Best place to buy denim (2009)
*Best place to buy denim (2014)
*Best place to buy DVDs (2010)
Best place to buy fashionable t-shirts (2010)
*Best place to buy fresh seafood (2008)
*Best place to buy fresh seafood (2013)
*Best place to buy furniture (2007)
Best place to buy geometric accessories made by local designers (2012)
Best place to buy jeans, Leader of Culture (2015)
*Best place to buy kitchen gadgets (2008)
*Best place to buy men’s shoes (2009)
Best place to buy men’s shoes (2014)
*Best place to buy men’s underwear (2008)
*Best place to buy music (CD or vinyl) (2011)
*Best place to buy new magazines (2011)
*Best place to buy records on the South Side (2010)
Best place to buy replicas of classic Chicago posters (2007)
*Best place to buy a skateboard (2007)
Best Place to Buy Something Scary (2018) 
*Best place to buy tea leaves (2010)
Best place to buy tea leaves in the suburbs (2010)
*Best place to buy a tie (2007)
Best place to buy toffee (2007)
Best place to buy a toy you can display as art (2012)
*Best place to buy a used bicycle (2009)
Best place to buy a wedding gift (2012)
*Best place to buy women’s jewelry (2009)
*Best place to buy women’s jewelry (2014)
*Best place to buy women’s shoes (2009)
*Best place to buy women’s shoes (2014)
*Best place to buy women’s underwear (2008)
*Best place to buy yoga clothes (2013)
Best Place to Celebrate Schubert (2018)
Best Place to Channel your Inner Botanist (2018) 
Best place to design your fantasy pad (2007)
Best place to design your own jewelry (2008)
Best place to donate a piano (2009)
Best place to find a nib (2016)
Best place to get books on street art and graffiti (2010)
*Best place to get eyewear (2011)
Best place to get gas before you enter the city (2002)
Best place to get a handmade belt buckle (2009)
*Best place to get men’s hats (2008)
Best place to get orthopedic shoes, Leader of Culture (2015)
Best place to get ready for a night out (2013)
*Best place to get women’s hats (2008)
Best place to get your golf fix in the city, Leader of Culture (2015)
Best place to get your kids and pets photographed (2016)
Best place to go when you’re supposed to go somewhere else (2019)
Best place to have your leather items cleaned (2013)
Best place to keep up with crime and mayhem, Leader of Culture (2015)
Best place to learn about pre-internet dating services in Chicago (2019)
Best place to live out “A River Runs Through It” (2009)
Best place to make going to the dentist dreamy instead of dreadful (2010)
Best Place to Mix Jazz and Table Tennis (2018) 
*Best place to open a checking account, now that the financial meltdown has wiped out a chunk of the banking system (2008)
Best place to play polo on wheels, Leader of Culture (2015) 
Best place to put your original zines and books on consignment and really make money (2014)
Best place to rent films about things your parents warned you about (2010)
*Best place to rent a limo (2007)
Best place to rent a tux (2007)
*Best place to sell your used books (2009)
*Best place to sell your used cds (2009)
Best Place to Shop Local and Feel Good (2018)
Best Place to Shop Small and Also Have Fun (2018) 
Best place to smell pretty (2002)
Best place to spend nothing on trendy duds (2008)
Best place to study Portuguese (2012)
Best place to sweat with a Russian (2012)
*Best place to take a music lesson (2007)
Best Place to Take Care of Your Tastebuds and Your Body (2017)
Best place to watch a baseball game, Leader of Culture (2015)
Best place to work out, shop and chill (2016)
Best Places to Pull Together Your Swaggerific, High-Low Chicago Style, An Essay (2016)
Best plus-size-focused clothing shop (2019)
Best Polish store (2009)
Best popcorn company with a logo reminiscent of Julie Andrews (2011)
Best poster shop(2008)
Best proof positive that the Far East can manufacture practically anything cheaper than the USA (2002)
Best public restrooms for visiting senators (2007)
Best reason to have second thoughts about Bank of America (2007)
Best Recognition of Chicago as a Global Cultural Force (2018) 
Best record store to dig for 45s (2013)
Best repair clinic (2016)
Best Retail/Art Therapy Store (2017)
Best retail resurrection (2016)
Best retail supply and display store (2010)
Best retro-fab barista fashion (2012)
Best retro luggage featured on a TV show about to get cancelled (2011)
Best retro lunch boxes (2010)
*Best running store (2007)
*Best running store (2012)
Best Sad Realization 1970s Chicago Is Long Gone (2018) 
Best Sad Realization 1980s Chicago Is Long Gone (2018) 
Best sale section in an indie bookstore (2014)
Best salon for a discount ‘do (2008)
Best salon for getting your Ramona Flowers on (2010)
Best Sanctuary for Hoops (2018)
Best selection of hanging Danish mobiles (2011)
Best seventies museum in a barbershop (2002)
Best Spa Treatment for Caffeine Addicts (2017)
Best spot for handmade silk lingerie inspired by the elegance of yesteryear, and leather outerwear inspired by the ethics of this year (2016)
Best store for moms (2014)
*Best street wear store (2014)
*Best sex shop (2008)
*Best shoe repair (2002)
*Best shoe repair (2007)
*Best shoe repair (2012)
Best shop for affordable, poofy tulle debutante ball gowns like Scarlett O’Hara once wore (2011)
Best shop to get your bike fixed at 9am (2009)
Best shop within a shop functioning as a gallery-rad gadget hub and recording space (2016)
Best shopping street or intersection (2014)
Best sign painters (2016)
Best sister stores with coordinating names (2010)
*Best smartphone app with Chicago relevance (2014)
*Best sneaker boutique (2010)
Best social service agency (2015)
Best Soul Music and Comfort Food Podcast (2018)
Best source of Chicago-made clothing, cards, jewelry and trinkets (2016)
Best specialty used bookstore (2010)
Best store for nerds, Leader of Culture (2015) 
Best store for pink girlie stuff (2008)
Best store for vintage costume jewelry sorted by color (2010)
Best Store Most Likely To Have Toppled Out of a Photo Spread in a Millennial Magazine (2017)
Best store to buy rehabbed hi-fidelity speakers (2013)
Best store to buy trinkets and doodads (2019)
Best store to loiter in on the Mag Mile besides the Apple store (2010)
Best strike-one-for-the-little-guy moment (2007)
*Best tailor (2007)
Best taxicab experience (2010)
Best thing about movie theaters with a bar or lounge (2016)
*Best thing about the Groupon craze (2010)
*Best thing you’d like to see the CTA spend your $3 fare on (2009)
Best thrift destination for brand-name clothes (2013)
Best thrift store in Chicago (2019)
Best thrift store that doesn’t remind you of a dimly lit elementary-school hallway (2019)
*Best toy shop (2008)
*Best toy store (2013)
Best underappreciated junk store (2010)
Best unheralded sound-recording engineer (2013)
Best use of a small piece of fabric (2016)
*Best used bookstore (2010)
Best used bookstore for wanderers (2013)
Best venue to record a studio-quality live album with your band for cheap (2013)
Best vintage-shop window display (2013)
*Best vintage store (2010)
Best voodoo shop (2010)
Best Voucher Program for Local School and Refugee Programs (2017)
Best way to cheer up in traffic (2015)
Best way to design a new home or office (2015) 
Best way to fight winter depression (2014)
Best way to get around the city by water without buying a boat (2015)
Best Way to Have a Vintage Adventure (2017)
Best way to profit from your giveaways (2008)
Best way to save money and still have fun (2009)
Best way to visit Spain without a plane (2009)
Best “we bring the spa to you” experience (2011)
Best weekend shopping development (2007)
Best wind-up tin robots (2011)
Best women’s-only workout space (2008)
*Best women’s shoe store (2011)
Best yogi, Leader of Culture (2015)
Made in Chicago: Best bet to learn everything there is to know about buttons (2019)
Made in Chicago: Best Chicago-made hypebeast (2019)
Made in Chicago: Best Chicago-made incubator (2019)
Made in Chicago: Best commercial snack cake invented in Chicago (2019)
Made in Chicago: Best made-in-Chicago harps since 1864 (2019)
Made in Chicago: Best traditional snack cake invented in Chicago (2019)

SPORTS & RECREATION

Best of the Best: Diversey River Bowl (2002)
Best of the Best: National anthem at Blackhawks games (2002)
Best of the Best: North Avenue Beach (2002)
Best of the Best: Sammy Sosa (2002)
Best of the Best: Sixteen-inch softball (2002)
Best of the Best: Soldier Field (2002)
Best of the Best: Southport Lanes (2002)
Best of the Best: Wrigley Field (2002)
*Best alternative name for the bean-bag game sometimes called corn hole (2007)
Best bar for fantasy-football dorks (2010)
*Best bar in Bridgeport to watch the White Sox (2011)
*Best bar in Wrigleyville to watch the Cubs (2011)
*Best bar outside of Bridgeport to watch the White Sox (2011)
*Best bar outside of Wrigleyville to watch the Cubs (2011)
Best basecamp for a running event (2013)
Best Bears bar (2012)
Best beer man at United Center (2010)
*Best bet as to which team gets to the World Series first (2013)
*Best Big Ten fans in Chicago (2012)
Best bike-friendly addition to the Lakefront Trail (2014)
*Best bowling alley (2008)
*Best bowling alley (2013)
Best boxing gym for beginners (2010)
Best brick-and-mortar place to seriously nerd out, old-school style (2011)
Best canoe or kayak launch on the Chicago River (2012)
*Best chance to win a championship THIS season (2013)
Best character on the Lakefront Trail (2012)
*Best Chicago baseball player this season (2008)
Best Chicago bird watcher (2014)
Best Chicago Bulls Homecoming (2018)
Best Chicago Cubs blog by a “chic” (2008)
*Best Chicago sports team owner (2013)
*Best city street to ride a bicycle on (2009)
*Best city street to ride a bicycle on (2014)
Best classic neighborhood pool hall (2010)
*Best coach of a Chicago pro sports franchise (2010)
*Best coach or manager of a Chicago team (2009)
*Best coach or manager of a Chicago team (2014)
Best craft bike maker (2014)
Best Cubs moment of joy in an otherwise sad season (2008)
Best ’85 Bear still making his living as an ’85 Bear (2002)
Best fantasy football team name with a Chicago Bear in it (2012)
*Best feature of the planned Wrigley Field renovations (2013)
*Best guess as to how long Tom Ricketts will be “patient” with Theo Epstein’s plan to build a winner (2014)
Best half marathon (2007)
Best half marathon (2009)
*Best half marathon (2014)
Best haven for Western New Yorkers (2012)
Best hope for the Bears to win the NFC North (2014)
*Best imaginary Twitter post by Mike Ditka (2009)
Best indulgence where the penance comes first (2009)
Best late-night shopping (2015)
*Best lesson to be learned from the Cubs season this year (2008)
Best local party game (2013)
*Best local sports blog (2009)
Best mobile bike repair service (2014)
Best monthly fun run turned5K (2012)
*Best name for the ballpark if the Rickettses decide to rename Wrigley Field (2009)
Best neighborhood 5K (2012)
*Best new Bear (2002)
*Best new Bear (2007)
*Best new Bear (2008)
*Best new Bear (2009)
*Best new Bear (2010)
*Best new Bear (2011)
*Best new Bear (2012)
*Best new Blackhawk (2002)
*Best new Blackhawk (2008)
*Best new Blackhawk (2009)
*Best new Blackhawk (2010)
*Best new Blackhawk (2011)
*Best new Blackhawk (2012)
*Best new Bull (2002)
*Best new Bull (2007)
*Best new Bull (2008)
*Best new Bull (2009)
*Best new Bull (2010)
*Best new Bull (2011)
*Best new Bull (2012)
*Best new career for Tank Johnson (2007)
*Best new Chicago baseball manager (2011)
*Best new Cub (2002)
*Best new Cub (2007)
*Best new Cub (2008)
*Best new Cub (2009)
*Best new Cub (2010)
*Best new Cub (2011)
*Best new Cub (2012)
*Best new gig for Jay Mariotti (2008)
*Best new gig for Rex Grossman (2008)
Best New Internet Streaming TV Channel (2017)
Best new park (2009)
*Best new Sox (2002)
*Best new White Sox (2007)
*Best new White Sox (2008)
*Best new White Sox (2009)
*Best new White Sox (2010)
*Best new White Sox (2011)
*Best new White Sox (2012)
Best new workout (2013)
Best news for Chicago bicycling (2010)
*Best next career for Ozzie Guillen (2007)
*Best next gig for Brian Urlacher (2013)
Best next move for the Baseball Hall of Fame after inducting Ron Santo (2011)
*Best nickname for Gordon Beckham (2009)
*Best nickname for Jay Cutler (2009)
*Best nickname to replace “the friendly confines” once Wrigley Field gets decked out in billboards and Jumbotrons (2014)
Best noticeable absence (2009)
Best park to let your dog off-leash (2013)
*Best personal encounter with a sports celebrity (2009)
Best pinball game in Lincoln Park (2014)
Best pinball game in Logan Square (2014)
Best pinball game in Wicker Park (2014)
Best place for a quiet bike ride (2013)
*Best place for bird watching(2014)
*Best place the Stanley Cup might have visited during its Chicago tour, but likely did not, at least not publicly (2010)
*Best place the Stanley Cup visited during its Chicago “tour” (2010)
Best Place to Appreciate the Genius of Jens Jensen (2018)
*Best place to buy Cubs tickets for sold-out games (2007)
Best place to go around in circles (2011)
Best place to picnic (2010)
*Best place to play board games (2008)
*Best place to play chess (2013)
Best place to play darts (2008)
*Best place to play kickball (2007)
Best place to run in Chicago (2012)
Best place to run where you aren’t supposed to run (2014)
*Best place to see a live sporting event (2013)
Best place to use protection (2014)
*Best place to watch Nebraska football games, as fans prepare for its Big 10 era (2010)
*Best place to watch soccer on TV (2008)
*Best player that the Cubs could have spent $30 million on instead of Milton Bradley (2009)
*Best post-Cubs-game bar (2008)
*Best potential buyer for the Chicago Cubs (2007)
*Best professional Chicago sports team other than Bears, Bulls, Blackhawks, Cubs or Sox? (2014)
*Best public beach (2010)
*Best public park (2010)
Best public pool to go swimming (2009)
Best public pool to have held Olympic swimming trials (2010)
Best public tennis facilities (2013)
Best race fiasco (2012)
*Best race other than the marathon (2007)
*Best race other than the Marathon (2012)
*Best reason the Bears will go back to the Super Bowl (2007)
Best reason to believe Northwestern is for real (2013)
Best reason to hold out hope for the Cubs (2013)
*Best replacement for Illini mascot Chief Illiniwek (2007)
Best section in the United Center to watch a Bulls game (2013)
*Best soccer bar (2013)
*Best sports bar to avoid Cubs fans (2007)
*Best sports bar to watch the Cubs pennant chase since you can’t get tickets for wrigley (2007)
Best sports-radio jocks (2008)
Best spot to spend a day on deck (2013)
*Best still-playing former Chicago athlete we wish were still in town (2010)
Best themed run (2012)
*Best thing about Northerly Island (2010)
*Best thing about the Bears playing in Champaign-Urbana (2002)
*Best thing about the Cubs’ Ricketts era so far (2010)
*Best thing about the Cubs-Sox World Series fantasy (2008)
*Best thing about the new Blackhawks regime (2008)
Best thing to happen on the South Side since Harold’s Chicken #17 opened (2014)
Best tweeting by a local sports personality (2009)
Best underrated park (2010)
Best way to spend $75 and get unlimited rides (2014)
Best weekend bike trip (2012)
Best Windy City Roller that we already miss (2009)
Best women’s-only workout space (2008)
*Best Wrigley Field renovation not yet proposed (2013)
*Best Wrigley renovation, not yet proposed (2002)
*Best yacht club in Chicago (2010)
*Best yoga studio (2011)