Chicago was something of a speakeasy capital during the Prohibition years, fueled largely by the bootlegging of prolific gangster Al Capone. And although the speakeasy’s purpose ended with the 1933 repeal of Prohibition, demand for speakeasy-style bars never truly fizzled out. Today, “secret” bars requiring a password for entrance are as popular as ever, as well as those decorated with the trappings of the 1920s and Prohibition era. Here are 15 hip retro bars where you can get a taste of the times without fear of legal retribution.
The Bassment
Tucked beneath The Hampton Social, this hopping Chicago speakeasy hosts in-house jazz, R&B and throwback bands nightly. The Bassment is four blocks west of AMLI River North. Enter through the alley door marked as a tobacco shop and walk downstairs.
353 W. Hubbard St., 312-386-5778
Bavette’s Bar and Bouef
French-inspired steakhouse Bavette’s is one of the more difficult places to secure a reservation in Chicago. But even if the main dining room is booked months in advance, you may be able to snag a table at the basement speakeasy below. Upon entering, head to the back of the restaurant and down the stairs. A seven-minute walk from AMLI’s River North apartments, this Chicago speakeasy serves Bavette’s full dinner menu.
218 W. Kinzie, 312-624-8154
The Drifter
During Prohibition, a green-painted door often indicated the presence of a speakeasy. And popular River North bar and restaurant The Green Door Tavern claims to have the last remaining Prohibition era speakeasy room, The Drifter. In addition to a daily rotating cocktail menu, The Drifter hosts nightly entertainment.
676-8 N. Orleans St., 312-631-3887
The Franklin Room
Another buzzing River North speakeasy, The Franklin Room is a proper Chicago tavern serving some of the city’s finest New American cuisine and handcrafted cocktails. One highlight for regulars is The Franklin Room’s Whiskey Keep program. Purchase a bottle of exclusive spirits from The Franklin Room, and the speakeasy will store the bottle for you to enjoy at your leisure. The Franklin Room is a 10-minute walk from AMLI’s River North apartments.
675 N. Franklin St., 312-445-4686
La Mez Agave Lounge
This Chicago speakeasy has a reputation for having a deep roster of talented mixologists. Choose a cocktail that strikes your fancy, and don’t be shy about requesting modifications. You can even name your spirit of choice and ask the bartender to shake you up a surprise. La Mez Agave Lounge is located in the lower level of Mercadito, a two-minute walk from AMLI River North.
108 W. Kinzie St., 312-329-9555
The Library at Gilt Bar
Gilt Bar’s craft cocktails and contemporary American cuisine receive generally favorable reviews. But patrons wax lyrical about Gilt Bar’s downstairs speakeasy, The Library. The low-lit basement bar, just five minutes’ walk from AMLI River North, is open on Thursdays, Fridays, and Saturdays.
230 West Kinzie St., 312-464-9544
Milk Room
Located between the Chicago Athletic Association’s Drawing Room and Game Room, the Milk Room boasts one of the Windy City’s most exclusive speakeasy bar experiences. Make a reservation well in advance of your intended visit to secure one or two of the Milk Room’s eight available seats. This Chicago speakeasy is a 20-minute walk from AMLI River North and the South Loop apartment rentals at AMLI 900 and AMLI Lofts.
12 S. Michigan Ave., 844-312-2221
The Office at The Aviary
Another exclusive Chicago speakeasy bar, the Office is a splendidly decorated 14-seat basement room beneath The Aviary, Grant Achatz’ inventive West Loop cocktail bar. You can pay a pretty penny for a reservation on Tock or reserve a table at The Aviary and hope your server invites you to check out the Office.
955 West Fulton Market, 312-226-0608
Room 13
Located beneath The Old Chicago Inn, Room 13 is a members-only Chicago speakeasy. Even members and their guests must don proper attire and recite an ever-changing password upon arrival to get in. But once you’re inside, it’s live jazz, 1920s-inspired cocktails, and strong speakeasy vibes at Room 13.
3222 N. Sheffield Ave., 773-472-2278
Three Dots and a Dash
Tiki bar meets Chicago speakeasy at Three Dots and a Dash, which specializes in exotic cocktails made with fresh cold-pressed juice. The entrance is tucked away on the alley east of Clark Street between Hubbard and Illinois. In other words, you’ll find Three Dots and a Dash across the street from AMLI’s River North apartments.
435 North Clark St., 312-610-4220
Untitled Supper Club
Unlike most Chicago speakeasy bars, Untitled Supper club doesn’t want for space. The 18,000-square-foot bar contains several lavishly decorated cocktail rooms, including a library-themed space. Untitled regularly hosts events, including a weekly burlesque show on Thursdays and lots of live music. Untitled Supper Club is just one block south of AMLI River North.
111 W. Kinzie St., 312-880-1511
Uptown Underground
Branding itself a purveyor of “top shelf retrotainment,” this Chicago speakeasy routinely hosts burlesque, cabaret, comedy and magic shows. Uptown Underground is a 10-minute Purple Line ride from Evanston’s Main Street stop, a five-minute walk from AMLI Evanston.
4707 North Broadway, 773-867-1946
The Violet Hour
If it weren’t full nearly every night it’s open, this Wicker Park speakeasy might be too hip for its own good. If you want to get in, don’t wear a baseball cap. And if you want to stay once inside, don’t use your cell phone or the word “bomb.” Dim lighting and the ever-changing mural adorning The Violet Hour’s facade do a good job of concealing the speakeasy’s door handle. But it is there, you just might have to feel around for it.
1520 North Damen Ave., 773-252-1500
Watershed Bar
Rounding off our list is one last River North speakeasy. Located beneath Pops for Champagne, Watershed Bar maintains an extensive cocktail menu, fine wine list and well-curated craft beer selection. The Chicago speakeasy is a five-minute walk from AMLI River North.
601 North State St., 312-266-7677
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