7 Top Secret Chicago Speakeasies You’ll Want To Sneak Into This Weekend

Charli Renken Charli Renken

7 Top Secret Chicago Speakeasies You’ll Want To Sneak Into This Weekend

*Knock, knock* What’s the password?

Speakeasies were a huge part of Chicago’s past and remain popular even today. These hidden gems harken back to the Prohibition when the jazz was hot, the burlesque hotter, and bootlegger booze was abundant. While modern speakeasies aren’t nearly as secret, they’re still a fun throwback to the 1920’s. Here are seven of our favorite Chicago speakeasies.


1. The Hyde, 5121 S Harper Ave

Photo courtesy of The Hyde.

The Hyde is as close as you can get to a real Chicago speakeasy without traveling back in time. The owners play up the 1920’s Prohibition vibe. There’s a portrait of Al Capone on the wall, red booths line the wall, and the bar is stocked nearly wall to ceiling with liquor. With the low-lighting, whiskey barrel tables, and lofted balcony, the vibe really makes you feel like you’re hiding out to drink giggle water in a real Chicago speakeasy. There’s also multiple shows of jazz, burlesque and more every night! More information.


2. Room 13 at the Old Chicago Inn, 3222 N Sheffield Ave

Photo courtesy of Fever

Room 13’s bartender serves up classic cocktails from the Prohibition era using ingredients from that time period. While serving you, the bartender will also share the history of your cocktail and the cultural significance it had in Prohibition America.

What makes this Chicago speakeasy particularly interesting is its monthly mind-reader shows! Psychic Speakeasy by skilled mind reader and psychic Jacob Mayfield entertains guests with an evening of ESP, cocktail conjuring, and divination in an intimate setting. More information.


3. The Green Mill Cocktail Lounge, 4802 N Broadway

green mill exterior
Photo: @kenzirkel

While The Green Mill is no longer a hidden bar, it plays an important role in Chicago history. During Prohibition, the lounge was a notorious speakeasy run by “Machine Gun” Jack McGurn, a known associate of Al Capone. Today, the Green Mill continues to play Jazz all night, seven nights a week. More information. 


4. Three Dots and a Dash, the alley of 435 N Clark St.

Three Dots Dash Chicago
Photo: Three Dots And A Dash

Beneath the streets of River North, the Three Dots and A Dash team dish up a tropical island get-away in the middle of Chicago. Head down an alley off W. Illinois Street – keep an eye out for the tiki torches! – and tropical vibes await. Although, as with so many precious hidden treasures, you’ll have to first contend with a forbidding Wall of Skulls. Worry not, though. Swoop right at the foot of the stairs to find the intimate Bamboo Room, a compact (maybe 16-seat?) bar offering its own menu of ‘simple yet refined’ rum creations. More information. 


5. Janitor’s Closet, 312 W. Chestnut St.

chicago speakeasy

Located inside an old custodian’s closet of the Fieldhouse Jones Hotel, Janitor’s Closet is exactly how it sounds. Mops, Pine-sol, and paint cans decorate the walls and patrons order handcrafted cocktails off a menu printed on a dishrag. Weird niche, but we’re into it!

Janitor’s Closet is a one-of-a-kind Chicago speakeasy with an intimate, surprisingly cozy atmosphere. It’s known for its handcrafted, rotating menu of cocktails by bartender Jef Tate. Among Janitor’s Closet’s most popular drinks is The “Brown line,” an L train-inspired drink with mezcal, tequila, pineapple, tamarind, and lemon. More information.


6. Mezcalito, 108 W Kinzie St

Photo courtesy of bread & Butter

Located in the basement of the popular Mexican restaurant, Mercadito, Mezcalito is a speakeasy-style bar with upscale Mexican cuisine and masterfully crafted cocktails. Succulents hang from the ceiling and neons light up the bar and aquarium tanks of Mexican art sculptures. The vibe of this Chicago speakeasy is perfect for catching up with friends in a low-lit, comfortable environment. This place also makes a killer margarita and hosts monthly Experimental Dinners, which give the culinary team an opportunity to show off their skills and try out new, mouthwatering recipes. More information.


7. The Ladies Room, 2957 W Diversey Ave

chicago speakeasy
Photo courtesy of Francis Son.

The Ladies Room harkens back to Cantonese brothels in a unique drinking experience located in the back of Fat Rice. Enter through to bakery to find a showcase of “global flavors and Midwestern terroir through house-made infusions, elixirs, and potions.” The Ladies Room recreates classic cocktails into imaginative reimaginings and features spirits like Ki No Bi Kyoto Gin, La Venenosa Costa Racilla, Navazos Cognac and other delicious liquors. More information. 


Feature photo courtesy of bread & Butter.

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