The 13 Best Speakeasies in Chicago, IL
Speak softly into the wind to gain entry to the best speakeasies in the Windy City! As the speakeasy capital of the United States during the Prohibition era, Chicago’s notorious reputation for providing lascivious fun and libations needs no introduction. However, what might require an introduction is the thriving collection of underground speakeasy bars still flourishing in the city’s underbelly. Take a look at the 13 best speakeasies in Chicago, IL.
The Drifter Chicago
676-8 North Orleans Street, Chicago, IL
(312) 631-3887
Hidden under Green Door Tavern, Drifter is a great choice when in the mood for a “show and cocktails” kind of night. Live entertainment hits the stage starting at 7 p.m. every Wednesday through Saturday. The bar’s rotating list of more than 100 cocktails gets switched up nightly to ensure that you always have a slightly different experience.
The Victor Bar
4011 North Damen Avenue, Chicago, IL
(773) 360-7049
A classy, moody interior offering balanced cocktails served by knowledgeable bartenders makes this speakeasy the easy choice. The Used Book cocktail made of rye, strawberry, Cynar, Meletti, and Angostura bitters deserves its own chapter! You can even simply follow the in-house custom of asking the bartender to surprise you with their best choice.
The Bassment
353 West Hubbard Street, Chicago, IL
(312) 386-5778
With a reputation as one of the best live music venues in Chicago, the Bassment doesn’t exactly do a stellar job of staying a secret. The amazing live acts, various lounge areas, electric dance floor, and thematic cocktails that are truly works of art all make this speakeasy worth seeing at least once in your life. The Bathtub cocktail is actually served in a tub-shaped cup with a rubber ducky and whipped-cream bubbles. The artisan baristas here also offer celebrity-themed cocktails featuring the faces of rock stars and songstresses etched in edible glitter.
The Library at Gilt Bar
230 West Kinzie Street, Chicago, IL
(312) 464-9544
Enter a basement through an anonymous side door to experience one of Chicago’s best speakeasies. Reservations are important at this small, impeccably decorated speakeasy textured with fringed chandeliers, jewel-toned velvet booths, and antique art. This is arguably one of the most beautiful bars in Chicago. There’s also no place better in the city to find a perfect martini.
Brando’s Speakeasy
343 South Dearborn Street, Chicago, IL
In addition to being featured in a number of television shows, Brando’s Speakeasy also has a habit of attracting Hollywood stars to its well-known karaoke stage. The VIP list here has included everyone from Cuba Gooding Jr. to George Lucas. The big draw is a cocktail menu featuring more than 25 martinis!
Revolver
1270 North Milwaukee Avenue, Chicago, IL
(773) 360-7491
Amaretto sours and dirty martinis are waiting in all their Prohibition-era glory at this newer addition to the Chicago bar scene. Crystal chandeliers, a triple-arch bar, and stunning décor feed into the classy vibe of Revolver. This is a great place to share drinks with the going-out crowd of Wicker Park.
Three Dots and a Dash
435 North Clark Street, Chicago, IL
(312) 610-4220
Throw out all of your expectations for a stodgy vibe when you show up at this Caribbean-themed speakeasy! The orchid-pinned, volcanic drinks will instantly put a smile on your face. The nice thing about this speakeasy is that it serves big portions of filling foods. The spicy Thai chicken and sweet potato fries are both winners.
Underground Cocktail Club
56 West Illinois Street, Chicago, IL
(312) 644-7600
You haven’t experienced Chicago’s bar scene until you’ve sat on a pink crushed-velvet couch at Underground Cocktail Club. This lively space brings patrons back to a time when speakeasies were gateways to jazz, dance, and rebellion. The vibe is pure 1920s glamour! The cocktail menu’s Raspberry Smash Bourbon featuring Jim Beam bourbon, Domaine de Canton, raspberries, lemon juice, and mint is truly the “mascot” beverage that sums up the strawberry-tinged vibe of this club.
Sparrow
12 West Elm Street, Chicago, IL
(312) 725-0732
The ultimate spot for a nightcap in Chicago, Sparrow is a Cuban-inspired speakeasy lounge that makes you feel like you’re in a swanky, retro hotel lobby. Its cocktail list is second to none! The barkeeps here can craft exceptionally flavorful and pure cocktails from the bar’s rye, scotch, bourbon, gin, vodka, brandy, whiskey, and liqueur collections. There’s also a menu of international sugar cane spirits.
The Meadowlark
2812 West Palmer Street, Chicago, IL
Perched in Chicago’s Logan Square, the Meadowlark offers an exceptional cocktail list concealed within its Birder’s Field Guide book. A seasonal menu of nibbles and desserts pairs beautifully with your drinks. Enter through Palmer Street to be greeted by a hostess ready to take you to your reserved section. With just five lounge areas available, planning ahead is a must!
Radio Room
400 North State Street, Chicago, IL
(312) 706-5228
Radio Room is a great place to get your signals crossed with an attractive stranger. What sets this speakeasy apart from others in Chicago is its massive size. Radio Room offers room for up to 400 people throughout its dining space, bar space, dancing space, and gaming space. Enjoy a full-service food menu combined with a bustling bar menu. While you’re indulging for the weekend, don’t skip the house-made beignets! This spot does a great job of upgrading a nostalgic space to satisfy modern appetites.
Grapes & Grains
858 West Lake Street, Chicago, IL
(312) 776-6552
Luring in lovers of all things vintage with its exposed brick and antique chandeliers in the heart of Chicago’s West Loop, Grapes & Grains is an expansive speakeasy lounge offering more than 2,500 square feet of space. Get cozy next to the baby grand, watch corks pop in the sabrage room, or simply slink into a booth concealed by low light in the back of the club. Pair a cheese and charcuterie board with reds for two for an unforgettable date night.
The Violet Hour
1520 North Damen Avenue, Chicago, IL
(773) 252-1500
Serving pre-Prohibition style libations in the heart of Wicker Park, The Violet Hour is an award-winning bar known for its seasonally rotating cocktail list full of stunners. The menu of stirred, shaken, hot, and house cocktails showcases what all cocktail menus aspire to be.
For more recommendations on where to eat and drink in the city, check out our Chicago page here!
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