Many of the watering holes on this list are intimate, but the Chicago Athletic Association's Milk Room is a true micro-bar, with just eight seats available to guests. Though the cocktails here cost a pretty penny (upwards of $40–$50 a pop), they're crafted with rare vintage spirits like 1970s Cointreau, 1960s rum and 1950s Fernet Branca. After you're done with the boozy history lesson, get some fresh air and take in the views upstairs at rooftop lounge Cindy's.
The secret drinking days of the Prohibition era might be long behind us, but Chicago is still home to a thriving network of underground bars perfect for grabbing a drink away from the crowds—and best of all, you (probably) don’t have to worry about the feds raiding these contemporary speakeasies. Venture beneath Chicago restaurants, behind closed doors and through alleyways to find clandestine bars offering intimate, dimly-lit settings and cocktail menus dreamed up by some of the city’s best mixologists, plus live music and other tempting attractions. Ready to drink on the down low? Here are some of the best speakeasies in Chicago, no secret password required.
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