The Best of Chicago’s Speakeasies

Untitled Supper Club

Throw it back to the roaring ’20s and experience the best of Chicago’s speakeasies. It’s no longer the Prohibition Era, but the city still holds plenty of underground bars that you can sneak away to for a night.


Inside the quirky and magic-themed cocktail bar lies the Vault, the Cauldron’s hidden speakeasy. Access to the Vault comes through the bank’s safety deposit vault. At this speakeasy, you can receive a wand-poured drink by the bank teller in exchange for wizard currency.


Featuring live music and karaoke, this speakeasy is a lounge of unique drinks, such as their Root Beer Old Fashioned. The hidden bar is decorated with vintage posters that make the bar as comfortable and familiar as a neighborhood haunt.


Through a record store recording booth you’ll discover Dorian’s. This intimate and retro speakeasy features live music and DJ’s, fully stocked with a wide drinks selection. Enjoy wine, beer, cider, mocktails, and interesting snacks such as Thai fried peanuts.

The Gatsby

The Gatsby is located on the second floor of Bourgeois Pig, an iconic Lincoln Park cafe. After the Children’s Memorial Hospital closed down the street, the owner took the opportunity to obtain a liquor license and open a speakeasy to boost business. The jazzy parlor features vintage ephemera, library-style shelves, and flickering candlesticks. To experience the charm, you’ll just need a password card from the cafe downstairs.

Three Dots and a Dash / The Bamboo Room

Taking on a Pirates of the Caribbean-esque style, Three Dots and a Dash is an immersive speakeasy with tiki torches. Located through a hidden door down a River North alley, the windowless room of glowing skulls serves rum-centric drinks served in famous tiki mugs.

Bringing more mystery and intrigue to the beloved speakeasy, Three Dots and a Dash added the Bamboo room. A speakeasy within a speakeasy, this hidden gem is a subdued, intimate space away from the crowds and the noise. It serves more refined drinks made with rum and rhum agricoles.


Inside the Green Door Tavern, take the metal stairs down to the bathroom. There, you’ll find a unique door covered in knickknacks. During the roaring ‘20s, this door housed a hidden speakeasy. Now, it’s home to the Drifter, a secluded cocktail bar of live entertainment. The constantly-rotating menu is available on custom-made tarot cards.


Below the rooftop lounge Cindy’s, Milk Room takes intimate to the next level with just eight seats available to customers. This hole-in-the-wall bar is no cheap joke, though: their cocktails can cost upwards of $28. These fancy drinks are crafted with vintage spirits like 1970s Cointreau, 1960s rum and 1950s Fernet Branca. 

Untitled Supper Club

Capturing the decor of a modern speakeasy, Untitled Supper Club is decked with green velvet and vintage furniture. With a whisky bar nestled in an elegant seating area, the club serves delicious cocktails and plays silent films on screens around the venue. Come for live entertainment, eccentric events, and delectable plates to pair with your cocktail.

Chicago Magic Lounge

Try drinks and a show at the Chicago Magic Lounge. Grab a cocktail and experience close-up magic at your table or live music performances on stage. Hidden through a laundromat, this theatrical speakeasy is serving incredible shows alongside delicious dishes like potato pancakes and fried chicken sliders.

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