The Raddest Speakeasy Bars in Chicago

Speakeasy Bars in Chicago

Chicago has a storied history with speakeasies, and even though prohibition ended in 1933, Speakeasy-inspired bars continue to thrive. The city’s undercover bars offers its own twist from hidden entrances, daily changing drink menus to a Luke Danes policy of no cell phone usage. We’ve created a list of the most rad speakeasy bars in Chicago including where to find them.

The difference between a speakeasy and a bar

Both places serve booze, but Speakeasies have a few distinct qualities. Today’s speakeasies are inspired by the prohibition era during the 1920s when selling alcohol was illegal. For that reason, speakeasies are often unmarked, underground or password protected. Many modern speakeasies will incorporate 1920s decor and popular drinks from that decade such as Old Fashions and Sidecars. Some speakeasies even offer live entertainment inspired by the prohibition era; think cabaret, jazz, and burlesque. 

 

The Library inside Gilt Bar

230 W Kinzie St, River North
Just like its name, The Library is lined with vintage books and elegantly styled with red velvet seating. Once inside Gilt Bar in River North, ask the staff to guide you downstairs to this intimate speakeasy. Enjoy classic cocktails and feel free to stay for dinner. Gilt Bar’s food menu (including vegetarian and gluten-free options) are available at The Library as well. Keep in mind, it is only open three nights a week: Thursday, Friday, and Saturday. Seating is limited, so try making reservations at the Gilt Bar and swap out to snag a seat for The Library.

 

Image source: Gilt Bar 

Booze Box inside Sushi Dokku

823 Randolph St. West Loop

A Japanese inspired speakeasy is one of the most original speakeasy concepts in Chicago. Come here for Japanese bites, an extensive sake menu, and Japanese beer.  Independent artists spinning vinyl and glowing red lights create a sexy, laid-back vibe. Find Booze Box beneath Sushi Dokku on Randolph Street in the West Loop. Enter through the back alley of Sushi Dokku and look for the giant red arrow.

 

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Bordel

1721 W Division St, Wicker Park

Hidden inside Black Bull, this lively Spanish speakeasy brings back the glamor of burlesque, the tap of cabaret dancers, a belief in magic, and the swing of jazz music. Walk through the mural wall inside of Black Bull and lead yourself to the excitement upstairs. You’ll find velvet galore in this eclectic and sexy speakeasy.  Visit Wednesday-Friday for live jazz, vaudeville, and cabaret shows. (BTW you might also check out “Things to do on a Wednesday in Chicago“)

Three Dots and a Dash

435 N Clark St. River North

Tiki torches guide you down the stairs where you’ll find this underground tiki bar.  Enjoy craft cocktails made with fine rum and spirits, fresh exotic fruit, and cold-pressed juices made in-house every day. Drinks are creatively served in themed glasses such as conch shells, tiki heads, and skulls. They are beautifully garnished with hibiscus flowers, brightly-colored straws, and pineapple leaves.  Look for the entrance in the alley, east of Clark Street between Hubbard and Illinois in River North. If you go on a Saturday night, the line forming outside this popular spot may give away the location.

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The Bassment Beneath the Hampton Social

353 West Hubbard Street Lower Level, River North

Don’t be fooled by the “tobacco shop” signage in the alley next to Hampton Social in River North. Peel back the black curtain, to enter a cocktail lounge with live music inspired by the 1960’s British invasion.  Offering signature cocktails named after powerful musical influencers, you can enjoy a Queen Bey, Adele, Tupac, the list goes on! The Bassment is open Wednesday-Saturday. Reservations are encouraged.

 

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A post shared by The Bassment (@thebassmentchi) on Oct 6, 2018 at 2:00pm PDT

Room 13

3222 N Sheffield Ave., Lake View

From the rotary phone to the bartender’s stories, Room 13 is a 1920s time warp. Dress to impress at this members-only cocktail bar which serves libations from the prohibition era (think whiskey, champagne, and gin cocktails). You’ll need to book a room at the Chicago Inn or become a Room 13 member to get this exclusive speakeasy. Just like Beyońce said, “to the left, to the left” of the alley of the Old Chicago Inn on Sheffield and Belmont is where you’ll find this Speakeasy. It’s marked with a red light and a sign reading “RM-13.” Knock on the door, provide the password, and you are in!

 

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A post shared by Room 13 at The Old Chicago Inn (@room13chicago) on May 9, 2018 at 6:54pm PDT

Violet Hour

1520 N Damen Ave, Wicker Park

Bring your most well-behaved pals to this elegantly decorated speakeasy in Wicker Park. To find it, look for an ever-changing mural and a singular light bulb. Once inside, candlelight illuminates this chic speakeasy complete with chandeliers, a long marble bar, and James Beard Award-winning cocktails. Be sure to follow the house rules (posted on the wall) which include a strict no cell phone policy. Note, there are no reservations here and the last seating is one hour before close. Check it out Sunday-Friday 6pm-2am and Saturday 6pm-3am. Happy hour goes until 8 pm Monday-Thursday.

The Drifter

676-8 N Orleans St, River North

Hate routine? So does The Drifter. Their daily-changing menu creates a unique experience for Chicagoans. Menus are printed on tarot cards and live performances create a lively atmosphere. It is also the only remaining speakeasy from the Prohibition Era; can this place be any cooler? Their slogan of  “Come as you are. Leave the way you want to be” invites consumers to enjoy an everlasting feeling of confidence. Located beneath the Green Door Tavern, remember your manners, and (if there isn’t a waitlist) lead with a knock first.

 

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A post shared by The Drifter (@thedrifterchicago) on Oct 3, 2018 at 7:18pm PDT

 

Watershed Bar

601 N State St, River North
This secret bar below Pops for Champagne offers Midwestern spirits and craft beers in a comfortable, no-frills setting. Lounge on a striped couch or opt for a wooden two-seater booth along the brick walls. This low-key lounge is a great escape from the hustle and bustle of the city, and conducive to good conversation. To find this speakeasy-style bar, enter Pops for Champagne, head to the right and look for the door with a “W” on it.

Milk Room

12 S Michigan Ave, Loop
The more intimate, the better. The Milk Room offers a night of eight patrons and an elegant atmosphere. Purchase tickets in advance ($50). If you’re lucky you may be able to walk in without a reservation. The Milk Room leaves two open seats each night. The vibe is moody with candelabras lighting the space. This speakeasy is located on the second floor of the Chicago Athletic Association.

 

 

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A post shared by Milk Room (@milkroomchicago) on Jun 29, 2017 at 9:31am PDT

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