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, porto. After you're done with the boozy history lesson, get some fresh air and take in the views upstairs at rooftop lounge Cindy's.
Al Capone and his famous mobster compatriots might be long dead, but the speakeasies—those seamy and secret bars that originally popped up during the Prohibition era—are alive and well in Chicago's drinking scene. Tucked beneath restaurants and hidden inside some of the best hotels in Chicago, the coolest Chicago speakeasies sling expertly crafted cocktails in an intimate setting. It doesn't hurt that many of these spots double as the best Chicago wine bars and jazz clubs.
You might notice that a few of the city's most beloved speakeasies, like The Bamboo Room inside of Three Dots and a Dash, don't show up on our list. That's because several spots have yet to reopen their doors (it's not easy to maintain social distancing guidelines in, say, a janitor's closet, after all). We'll keep this list updated as more bars reopen. In the meantime, here are some of the best speakeasies in Chicago—no secret password required.
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