Picture yourself in 1931 – the height of prohibition. You’re a young fella getting off a hard day’s work and hitting the streets of Chicago. You’ve got a fat new paycheck in the back of your pocket and you’re lookin’ for a good time and a stiff drink tonight. But how do you find it if alcohol has been outlawed? You find a speakeasy, of course.
Illegal drinking dens, or speakeasies, were some of the only places you could buy booze during the Prohibition Era of 1920-1933. Anyone who came to buy alcohol had to whisper a code word to enter. That’s how the name “speakeasy” came about.
During that time, Chicago was a hotbed of hooch bootlegging, and, as a result, this rich history has been part of the city’s fabric for decades. To capitalize on the fun, modern bar owners there have embraced the idea of a tavern that’s difficult to find and even harder to get inside.
Below are five of Chicago’s best speakeasies with a few of their secrets revealed. Just be sure to make tracks if the coppers show, ya hear?
1. Milk Room
The Milk Room is ultra private, ultra exclusive and was once a genuine speakeasy during Prohibition. Located on the second floor of the Chicago Athletic Association, this 8-seat microbar will only let you in if you make advance reservations. If you’re lucky enough to get on that list, throw back a whisky or two from their selection of rarities.
2. The Drifter
Under the historic Green Door Tavern (River North) is what was once a genuine speakeasy called The Drifter. The revolving menu of cocktails is presented on Tarot cards. Burlesque dancers shimmy nightly for your pleasure. It’s so popular, there’s actually a waiting room to get in at the bottom of the stairs somewhere in the back of Green Door Tavern.
3. Chicago Magic Lounge
You know those nights where you need a place to launder your money, have a drink and catch a magic act? Proceed through a working laundromat somewhere in south Andersonville to enjoy a Sleight of Hand while you watch some sleight of hand at Chicago Magic Lounge.
4. The Ladies Room
Back in the day, speakeasies were often hidden behind other, more respectable-looking businesses. The Ladies Room lounge is in the back of Fat Rice bakery. Powder your nose in the ladies room here and you may find yourself with a One Way Ticket to Bangkok.
5. The Violet Hour
You’ll find the door to this secret establishment somewhere within an ever-changing mural on Damen Avenue in Wicker Park. If you make it inside, reward yourself with a Woolworth Manhattan.
While these watering holes are no longer so secret, for those looking for a quirky, boozy night on the town, these establishments will fit the bill…dollface.