Pops for Champagne (backroom bar by fireplace) then W Hotel on Adams (second level bar)
Make the phone call, use the two-way, either way these two places are the perfect spots to meet the woman you aren’t supposed to be with and lessen your chance of getting caught with her. There’s a certain mood of romance at both, drinks are on-point, and they give the girl you are with the feeling that she’s not playing second fiddle to your main girl. The fireplace at Pops (especially if you get to sit by it) is the mood setter, order the Mums (it’s sweeter than Moet, hint), finish the bottle, then drive (in separate cars) to the W for the nightcap. Once you get to the dark, sexy second floor bar order the apple martini, feed “honey” the granny smith slice once the drink is empty, then ask her one question: What would you like to do now? Just remember to tip the concierge the next morning. Never, under any circumstances, take your girl/wife to either of these two spots.
Pops for Champagne, 601 North State, (312)266-7677
Hotel W, 172 West Adams, (312)332-1200
Best of Chicago 2002