A long time ago, there were secretive gems scattered around the city. It was a lucrative time for lavish hideaways, where the jazz was steamy, and the burlesque burned down the house. While the Prohibition Era is now only thought of in history books where bootleggers are an old tale, clandestine bars are more prevalent than others. While speakeasies aren’t nearly as hidden, they’re still a place to sling back a cocktail in a decadent space. There are many low-key treasures around the city, from a hotel room turned bar in the sky to a covert barbershop—hidden in plain sight, here are our favorite speakeasy Chicago bars.
Mile High Cocktail Club
The first on our list is perched high above the Magnificent Mile at the Four Seasons Hotel. This exclusive cocktail destination is one to remember, filled with vibrancy, style, and immersive drinks. The experience starts before you even take off.
When you check in, you’ll be given a glass of champagne and a room key to the hidden lounge on the 46th floor. There, you’ll embark on a gilded journey through inventive cocktails inspired by the most exquisite and spectacular sunsets from around the globe.
📍Address: 120 E Delaware Pl, Chicago, IL 60611
📲 Reservation: Make a reservation at Mile High Cocktail Club here
The Lounge
The new nightlife hot spot near Fulton Market. Upstairs at Nisos, The Lounge is an alluring, hidden cocktail lounge (hint: look for the bookshelf) tucked away on the second floor of Nisos Prime. The 2,000-square-foot room offers a wondrous, carefree late-night experience full of energy and music and transports guests to the nightlife of the Mediterranean.
This decadent party space offers nightly DJs (Fridays and Saturdays), table experiences, and a unique craft cocktail program. It’s open Thursday—Saturday.
📍Address: 802 W Randolph St Floor 2, Chicago, IL 60607
📲 Reservation: Make a reservation at The Lounge here
The Milk Room
What once was a speakeasy Chicago bar during Prohibition is now a hidden eight-seat microbar with a curated selection of whiskey and other rare vintage spirits. Located in the Chicago Atheltic Hotel, you can first take in the city views of Cindy’s rooftop and then head to The Milk Room for an intimate evening.
📍Address: 12 S Michigan Ave, Chicago, IL 60603
📲 Reservation: Make a reservation at The Milk Room
Soif Wine Lounge
Located below Testiaccio, Sofio Wine Lounge transforms into a Parisian escape. The inviting room is a dimly lit bar that skews red and is adorned with oversized velvet chairs, vintage tables, and candles. Select a drink from their curated collection of French wines that will transport you to the south of France.
📍Address: 2456 N California Ave, Chicago, IL 60647
📲 Reservation: Make a reservation at Sofi Wine Lounge here
Blind Barber
There are not many Chicago speakeasy bars where you can cut your hair in the afternoon and dance to a DJ at night. The Blind Barber fronts as a barber shop, but once you head to the back, the space opens into a ’70s-themed bar with cocktails and a spacious dance floor.
📍Address: 948 W Fulton Market, Chicago, IL 60607
📲 Reservation: Make a reservation at Blind Barber here
The Drifter
Located underneath the basement of the Green Door Tavern, the Drifter is an authentic 20s-era that sparks discreetness while still transforming into an ostentatious space. When you step into The Drifter, you’re stepping on the same floor where drifters have tread for over 100 years.
With a rotating list of over 100 cocktails presented on Tarot cards and nightly performances, this hidden gem is perfect for cocktail enthusiasts and history buffs alike.
📍Address: 676-8 N Orleans St, Chicago, IL 60654
📲 Reservation: First come, first serve
Nine Bar
Nestled in the back of Chinatown’s oldest restaurants sits Nine Bar, a new Chicago speakeasy bar, right behind Moon Palace Express’s (formerly known as Moon Palace Restaurant) signature countertop. The bar is the first of its kind to exist in the area.
While plenty of karaoke options and mixed drinks are available at restaurants in the area, Nine Bar is the only place dedicated to serving up a one-of-a-kind bar atmosphere. The ambient space is extraordinary, with a full menu of bites and entrees, serving specialty cocktails, spicy dumplings, and strong drinks.
📍Address: 216 W Cermak Rd, Chicago, IL 60616
📲 Reservation: Make a reservation at Nine Bar here
Nightshade Bar
Located in Portage Park, it is one of the Chicago speakeasy bars that doesn’t take reservations, so your best bet is to opt for a walk-in after dining at the upstairs Moonflower. The bar is only open Friday and Saturday from 6 p.m. to 1 a.m. Offering shaved ice cocktails, beer, wine, and cocktails with names like Up All Night and Picture Perfect.
📍Address: 359 N Milwaukee Ave, Chicago, IL 60641
📲 Reservation: Make a reservation at Nightshade here
Three Dots and a Dash
Beneath the streets of River North, the Three Dots and A Dash team dish up a tropical island getaway in the middle of Chicago. Head down an alley off W. Illinois Street—watch 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. 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.
📍Address: 435 N Clark St, Chicago, IL 60654
📲 Reservation: Make a reservation at Three Dots and a Dash here
Sushi By Bou
While not exactly a Chicago speakeasy bar, this restaurant will wow you. Prepare for an experience unlike any other– a new Chicago sushi speakeasy serving delicious omakase at the Emily Hotel is open and ready to impress. Transporting guests to the 90s brings an intimate dining experience to the masses with a unique drink list and menu options meant to surprise and delight!
📍Address: 311 N. Morgan St, Chicago, IL 60607
📲 Reservation: Make a reservation at Sushi by Bou here
Mezcalito
Located in the basement of the popular Mexican restaurant Mercadito, Mezcalito is a speakeasy-style bar with upscale Mexican cuisine and masterfully crafted margaritas. Succulents hang from the ceiling, and neons light up Mexican art sculptures’ bar and aquarium tanks.
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, allowing the culinary team to show off their skills and try out mouthwatering recipes.
📍Address: 108 W Kinzie St, Chicago, IL 60654
📲 Reservation: Make a reservation at Mercadito here
Pigtail Cocktail
The River North speakeasy is below Chef José André’s renowned restaurant, Jaleo. Similarly, the hidden bar channels the flavors of modern-day Spain, but this time, it draws inspiration predominantly from Spain’s trendy cocktail scene. The Pigtail cocktail menu from Miguel Lancha featured drinks made from Andrés’ favorite ingredient, jamón ibérico.
Try out the Consomé Cocktail, which combines a house-made pork consomé, the Negroni Cristal, which is fat washed in ibérico ham, or a mezcal distilled with an entire jamón ibérico leg hanging in the still. Vegetarians, this one might not be for you!
📍Address: 500 N Clark St #465, Chicago, IL 60654
📲 Reservation: Make a reservation at Pigtail here
The Violet Hour
The Violet Hour’s entrance is a discrete single door blended into the exterior’s ever-changing mural. Once you find the handle, you’ll find three salon-inspired rooms with a cluster of candlelit tables reminiscent of the prohibition era. Their seasonally rotating cocktails are refreshing and award-winning.
📍Address: 1520 N Damen Ave, Chicago, IL 60622
📲 Reservation: Make a reservation at The Violet Hour here
Dorian’s
A record store by day and cocktail lounge by night. Once you enter Dorian’s, the space transforms into a low-lit, cozy lounge that echoes elegance and a lively atmosphere. Dorian’s has a center stage with nightly live music from disco beats to a Jazz band.
📍Address: 1939 W North Ave, Chicago, IL 60622
📲 Reservation: Make a reservation at Dorian’s here
Bodega Taqueria y Tequila
Bodega Taqueria y Tequila brings a relaxed vibe composed of a front ‘shack’ where customers can pick up fast, delicious eats and a speakeasy-style lounge in the back filled with high-quality drink options in a swanky setting. Whether you choose to stop by the front-facing Airstream trailer (located inside a casual brick-lined space) for a quick bite to eat or make reservations for the decked-out lounge in the back, Chicago’s new Bodega is sure to please.
📍Address: 912 W Randolph St, Chicago, IL 60607