Speakeasies were a huge part of Chicago’s past and remain popular today. These hidden gems harken back to the Prohibition Era when 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 1920s. There are so many cool hidden gems around the city, so we rounded up our favorite speakeasy Chicago bars for you!
1. 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
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
3. 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
4. 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
5. 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
6. Room 13
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 your cocktail’s history and its cultural significance 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.
📍Address: 3222 N Sheffield Ave, Chicago, IL 6065
📲 Reservation: Make a reservation at Room 13 here
7. 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
8. 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
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
10. 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
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
12. 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
13. The Lounge
The new nightlife hot spot near Fulton Market. Upstairs at Nisos, The Lounge is an alluring, tranquil space hidden behind a bookshelf. It’s the perfect place to have a carefree late-night experience and be transported to the liveliest nightlife of the Mediterranean. This decadent party spot will offer nightly DJs, table experiences, and a unique craft cocktail program.
📍Address: 802 W Randolph St Floor 2, Chicago, IL 60607
📲 Reservation: Make a reservation at The Lounge here