Looking to add a certain je ne sais quoi to your weekend routine? Speakeasies have just the right kind of mystique to make your night out one-of-a-kind.Once upon a time, when the Feds put a ban on alcohol, Chicago was the nation’s breeding ground for speakeasy bars. Though legislation repealing Prohibition was ratified back in 1933, our cultural fascination with the Prohibition era (and with much of the mob activity that marked it) keeps us going back to basements and backrooms made to emulate that time in our history.
Not only can one find a swanky, dimly-lit environment that evokes the shady underworld of Al Capone, but creative and delicious cocktails have also become a hallmark of the (sometimes) password-protected, contemporary speakeasies in Chicago. Better yet? We’ve got all the keys to getting inside even the most hidden of speakeasies bars.
The Drifter
676-8 N Orleans St, Chicago, IL 60654
This bar is everything a speakeasy should be, with an intimate space, hidden entrance, unique performances, creative drinks, and the right amount of kitsch. In fact, it’s an original, dating back to the Prohibition Era. Just enter the Green Door Tavern and head down the stairs in the back to find this speakeasy bar in Chicago. You’ll be placed in a waiting room, most likely, since the bar’s capacity is a meager 37, but trust us, a visit here is sure to be a memorable one.
Watershed
601 N State St, Chicago, IL 60654
We’d consider this bar to be a more subdued version of a speakeasy—perfect for a relaxed gathering. The underground, dimly lit space has comfortable seating and a menu that exclusively features regional spirits and beers. Just stroll into Pops for Champagne and take the stairs at the back corner of the bar to discover Watershed.
Three Dots and a Dash
435 N Clark St, Chicago IL 60654
Over a summertime weekend, the line for this tiki-style speakeasy bar in Chicago can easily stretch down the alley outside. Luckily, the fruity concoctions are pretty fantastic and the bar bites are delicious, so it really is worth it to brave the line. Keep it classic with a Mai Tai, or try something new with the Trouble in Paradise: Japanese whiskey, toasted sesame, and Sirop de Canne.
Brando’s Speakeasy
343 S Dearborn St, Chicago, IL 60604
For those curious enough to venture into the Loop, Brando’s Speakeasy is the perfect first stop. Enjoy a fine-crafted cocktail from their sumptuous drink menu, or join the party at the karaoke lounge. Not a night owl? No problem. Check out Brando’s for their awesome happy hour specials: Monday–Thursday, 5–7 pm. And, to be fair, this one isn’t all that hard to find. We won’t even tell you how.
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Booze Box
823 W Randolph St Downstairs, Chicago, IL 60607
For small bites and sake aplenty, there’s Booze Box. Located under Sushi Dokku, this hangout is great for those looking to indulge in late-night Japanese cuisine. Relax under the cozy red lamps and sample small plates, like the spicy tuna maki and crab deviled eggs. First head to Sushi Dokku, then take the alley around the corner until you find a door with a little sticker that reads “Booze Box.”
Milk Room
12 S Michigan Ave, Chicago IL 60603
The Milk Room is a tiny speakeasy bar in Chicago that sits on the second floor of the Chicago Athletic Association. It accommodates just 8 chairs, serves up “spirit-forward” cocktails, and prides itself on using high-quality and hard-to-find ingredients.
The Franklin Room
675 N Franklin St, Chicago, IL 60654
Whiskey aficionados, this one’s for you. Located in the River North neighborhood, The Franklin Room features fare for all; whether you’re looking to indulge in their exquisite tavern menu or take a look at their exclusive whiskey collection, there’s something for every party. Sure, the door is hiding in plain sight, but the bar itself is subterranean, making it feel like a retreat away from the hustle and bustle of the city. And as an added bonus, oysters are $1 every day, from 5–6:30 pm!
Chicago Magic Lounge
5050 N Clark St, Chicago, IL 60640
Chicago Magic Lounge is sure to make your night out anything but dull. Serving up magic tricks in a speakeasy-style atmosphere, it can’t get any weirder than downing a How Houdini Died cocktail and watching it fill up again on its own (just kidding, this doesn’t actually happen here… but it’d be cool). Enter this unassuming speakeasy bar through a laundromat on Clark Street and find a massive theatre space hiding just beyond the washing machines.
Bordel
1721 W Division St, Chicago, IL 60622
Featuring Prohibition-style cocktails, burlesque shows, and a warm-lit ambiance that takes you back to the early years of the 20th century, Bordel is one of the most authentic-feeling speakeasies in Chicago. You’re almost convinced this place really has been here for 100 years, but this modern concept is just a seriously good disguise for a great cocktail bar. You’ll find this on the second floor of Black Bull, a Spanish restaurant on Division. The unmarked door to the right of the Black Bull entrance leads up a flight of stairs, where you’ll be treated to all kinds of burlesque entertainment.
Janitor’s Closet
312 W Chestnut St, Chicago IL 60610
Located at the Fieldhouse Jones, this intimate space includes just 15 seats for its guests to experience intriguing craft cocktails, which include flavors from both around the world and close to home in the Midwest.
Room 13
3222 N Sheffield Ave, Chicago, IL 60657
The Old Chicago Inn is secretive enough without its hidden speakeasy, but Room 13 just builds the allure. The recipes used in the cocktail-making here are as ancient as the Prohibition itself, but still totally enticing, and with a dress code that encourages 1920s style, Room 13 is, in the best way, stubbornly faithful to its theme. Book a room at the Old Chicago Inn to get exclusive access to this speakeasy bar.
The Violet Hour
1520 N Damen Ave., Chicago, IL 60622
Easily the classiest speakeasy on this list, The Violet Hour takes on an ambiance worthy of the Great Gatsby. Featuring inventive and tantalizing cocktails like Alpha, Bravo, Charlie, Delta and Penguin’s Suit, you’ll be transported back to the scandalous Prohibition-era as you sip on your gin.
There’s a mural on Damen Avenue that looks like a series of steam-punk clockwork. Find the handle by feeling your way along and you’ll be rewarded by the best speakeasy in Chicago.
Dead Plants
1134 W. Washington Blvd., Lower Level, Chicago, IL 60607
Dead Plants at The Press Room brings the speakeasy experience from the 1920s into this century by launching a live music series on the second Saturday of each month. Priced at $45 per person, each ticket will include a 90-minute show and one cocktail. Doors open at 8:30pm and the show will start at 9pm. Only 26 tickets will be available per show, guaranteeing an intimate live-entertainment event.
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Featured Image Credit: The Franklin Room Instagram Page
