The Matchbox Be warned: The Matchbox is the bar you go with only those friends who brush their teeth, shower daily, and know that organic deodorant is bullshit, because you’ll be getting close. For this reason, it’s also a great place for a date, but only with someone you’ve been out with before—the Matchbox brags that it’s Chicago’s “Most Intimate Bar.” The bartenders are always happy to shake up something special for the indecisive cocktail drinker, but the house margarita is a can’t-miss, served with powdered sugar on the rim and a lemon peel. But the best nights at the Matchbox are in the dead of winter, when the windows fog up, the patrons crowd in from the cold, and hot-buttered rum can be ordered by the mug. 770 North Milwaukee, (312) 666-9292, facebook.com/pages/The-Matchbox
