Debonair Social Club

This two-floor club is a holdover from Wicker Park's past as a nightlife destination—a time long before chain restaurants and shoe stores began taking over the neighborhood. Now, Debonaire Social Club is one of the only places on this stretch of Milwaukee Avenue where you can order bottle service and dance to music until the wee hours of the morning. Stop by during the weekends for parties that span multiple floors, with one DJ providing the soundtrack upstairs and another spinning tunes in the basement.