Speakeasies were a huge part of Chicago’s past and remain popular even today. These hidden gems harken back to the Prohibition Era 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 1920s. There are so many cool spots based in Chicago, so we rounded up 10 of our favorites!
1. The Grand Cabaret Speakeasy 1132 W Grand Ave.
When the weather dips to unbearable temperatures, experience the light and heat indoors with a tantalizing spectacle of top-rated Grand Cabaret shows taking place this winter in a hidden back room space in the West Loop’s Porkchop restaurant at 1132 West Grand Avenue.
Read more about Grand Cabaret here.
2. Room 13 at the Old Chicago Inn, 3222 N Sheffield Ave
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. Find more information about Bar 13 here.
3. Nine Bar, 216 W. Cermak Road, Chicago, IL 60616
Nestled in the back of Chinatown’s oldest restaurants sits Nine Bar, a new lounge that’s hidden speakeasy-style right behind Moon Palace Express (formerly known as Moon Palace Restaurant) signature countertop. The bar is the first of its kind to exist in the area. While there are plenty of karaoke options and mixed drinks available at restaurants in the area, Nine Bar is the only place dedicated to serving up a one-of-a-kind bar atmosphere. With a full menu of bites and entrees, the ambient space is extraordinary, serving up specialty cocktails, spicy dumplings, and strong drinks. Make a reservation at Nine Bar here.
4. The Green Mill Cocktail Lounge, 4802 N Broadway
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. Find out more information on Green Mill here.
5. Nightshade Bar, 4359 N. Milwaukee Ave.
Located in Portage Park, the small bar doesn’t take reservations so your best bet is to opt for a walk-in after dining at the upstairs Moonflower. The speakeasy is only open on Friday and Saturday from 6 p.m. to 1 a.m. Offering shaved ice cocktails along with beer and wine and cocktails with names like Up All Night and Picture Perfect. Make a reservation here.
6. Three Dots and a Dash, the alley of 435 N Clark St.
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 – 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. 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 can be found here.
7. Sushi By Bou, 311 N Morgan St.
Prepare for an experience unlike any other– a new sushi speakeasy serving up delicious omakase situated at the Emily Hotel is open and ready to impress. Transporting guests to the 90s, it brings an intimate dining experience to the masses with a unique drink list and menu options that are meant to surprise and delight! Book a reservation here.
8. Mezcalito, 108 W Kinzie St.
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 mouthwatering recipes. More information can be found here.
9. The Roar on Rush, 437 N Rush St.
The cocktails at this interactive hidden speakeasy in downtown Chicago are so delicious, it’s almost illegal. If you’ve ever felt enamored by Prohibition Era tales from the times of Al Capone, now is your chance to experience it at this hidden Prohibition-style speakeasy. Open in Chicago, this speakeasy experience includes drinks, food, and live performances that’ll transport you back in time. Sip on different delicious spirits in each room, courtesy of Chicago’s Wolf Point Distillery. With 4 different tasting rooms, you’ll have to enter a secret passageway to access this one-of-a-kind cocktail experience set in the Prohibition Era. For more information on The Roar on Rush, head here.
10. Pigtail Speakeasy, 500 N Clark St #465
The River North speakeasy is located right below Chef José Andrés renowned restaurant, Jaleo. The hidden bar, in a similar vein, channels the flavors of modern-day Spain only 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. Vegetairians, this one might not be for you! Make a reservation here.