The Secrets to Getting In to 5 Real Chicago Speakeasies

Photo Credit: Instagram


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

Photo Credit: 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

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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

Photo Credit: 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

Photo Credit: Mark Much

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

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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.