Cindy's unfurls awesome views of Millennium Park and the lake from atop the Chicago Athletic Association Hotel. Sit at one of the long wood tables under twinkling lights and sip snazzy cocktails with ingredients such as orange saffron bitters. Alas, everyone wants in on the action, so come early to avoid having to wait for a seat.
It's also worth checking out the other bars in the building, including the Cherry Circle Room (like a handsome, low-lit supper club) and the lively Game Room (with pool, Foosball, table shuffleboard and even a bocce court).
