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Guide to Chicago Speakeasies

Updated: May 10, 2024
 By Mel

Though the Prohibition Era is thankfully long gone, Chicago remains fascinated by the idea of speakeasies. There are many around the city that can be found through hidden doors, in back alleys, and behind murals.  These now legal drinking establishments will bring you back in time and remain some of the best kept secrets in Chicago. Read through this guide to find the best speakeasy in a neighborhood near you!

Wicker Park Speakeasies

Wrigley Field Speakeasies

Top 10 Rooftop Bars in Chicago


History of Chicago Speakeasies

River North Speakeasies

West Loop Speakeasies

History of Speakeasies in Chicago

In 1920, the United States passed the 18th Amendment, the Volstead Act, more commonly known as Prohibition.  With the passing of this Act, the production, transportation, and sale of alcoholic beverages was now illegal.  This new law, meant to make the United States more moral, only generated further criminal gang activity and corruption.  This also led to the invention of speakeasies, illegal drinking establishments.  

Also referred to as a blind pig or blind tiger, the root of the name comes from the fact that you need to speak easy, or quietly, in public about such places, and while inside the establishment, to not broadcast such illegal activity to the cops and neighbors.

During the 13 years of prohibition, speakeasies popped up across the country.  It is believed that for every legal bar pre-prohibition, 6 speakeasies materialized in its place during prohibition.  These were found in basements, warehouses, and hidden behind store fronts.  The easy money made speakeasies popular to start, and worth the risk. Owners and bartenders were often part of a gang, or conspiring with the gangs, to smuggle in the booze, and pay off the cops if need be.

Chicago is a city that is infamous for the gangs of the 20’s and speakeasies that erupted  across the city.  With gangsters such as Al Capone and Bugs Moran running the streets, it is no wonder why. But with the repeal of Prohibition in 1933, speakeasies were no longer necessary.  However, they are still living on in Chicago culture.

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River North Speakeasies

1. The Bassment - River North, 353 W Hubbard St, Lower Level

Hidden beneath The Hampton Social you will locate this secret bar that pays tribute to the 1960’s British Invasion in its decor. Beyond the velvet and leather couches is a full stage for the live entertainment that takes place each night.  From jazz to throw back bands, this space is great cocktail lounge to relish the drinks and live entertainment.

How to Enter: Go through the door marked as a tobacco shop in the alley to find the stairs leading down to this cocktail lounge.

2. The Drifter - River North, 676 N Orleans St

Unlike many speakeasies in the city today, this cozy space served as an authentic speakeasy during the years of Prohibition. This basement level bar provides a changing menu inspired by and written on tarot cards that are chosen each night. Be prepared for the random entertainment and burlesque shows that take place during the course of the night!

How to Enter: Go through the Green Door Tavern, past the bar, down the stairs towards the bathroom. Knock on the door to get inside, but be ready for a wait, as the capacity is only 37.

Photo: @the_traveling_zam 

3. Watershed - River North, 601 N. State St.

With a 1970’s decor, this lounge features an extensive cocktail menu, as well as craft beer, artisanal spirits, and wine from the Great Lakes region.  This warm and comfortable space has something for every kind of drinker, and provides a needed escape from the streets of downtown.

How to Enter:  Go through Pops for Champagne and go down the stairs in the southeast corner.  

4. Untitled Supper Club - River North, 111 W. Kinzie St.

This expansive space is divided up into various tastefully decorated rooms, including a Whiskey Library and Champagne Dinning Room. Live entertainment is another attraction to this secret space, including burlesque shows on Thursdays and live music throughout.  The impressive whiskey selection is another exciting feature.

How to Enter: This underground space is found through a secret door and down the stairs.  

Photo: @50proof

5. The Library - River North, 230 W. Kinzie St.

What better place to sip a craft cocktail then in the cozy Library found beneath Gilt Bar.  Surrounded by shelves and shelves of vintage books, this intimate space provides the food and drink menu of the bar upstairs, but a quieter atmosphere to enjoy your company.

How to Enter: Open only Thursday-Saturday, ask the hostess to bring you to the Library, found through the unmarked door downstairs by the bathrooms.

Three dots and a dash

6. Three Dots and a Dash - River North, 435 N Clark St.

Escape into this hidden tiki bar, with expert cocktails perfected with spices, exotic fruit, andcold pressed juice produced daily.  This tropical oasis provides an excursion as you sip cocktails from a skull glass in this speakeasy vibe bar between the bustling streets of River North.

How to Enter: Enter the alley east of Clark St., between Hubbard and Illinois by Firecakes Donuts.  When you see the line, you know you have arrived!

Photo: @cahill2

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West Loop Speakeasies

7. Booze Box - West Loop, 823 W. Randolph

Booze Box

This speakeasy-style is found in the back alley of Sushi Dokku’s.  Once you enter, you will discover a dark space lit by red lanterns, allowing for a perfect date spot with a laid back atmosphere.  Order Japanese drinks and street food with hip-hop playing on the speakers in the background.

How to Enter: Make your way through the back alley located south of Sushi Dokku.  Follow the red arrow through a door labeled with a Booze Box sticker on the handle, and the staircase beyond will lead you to the hidden bar.

Photo: @wheresshegoing

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Wicker Park Speakeasies

8. The Violet Hour - Wicker Park, 1520 N. Damen Ave.

Masked behind an ever-changing mural on Damen Avenue lies the Violet Hour.  Look carefully for the door handle, and soon you will be seated in the low-lit, intimate bar with towering booths, and award winning cocktails. These intricate drinks and the intimate atmosphere make it a spot you will not want to miss.  But do not forget to follow the house rules, including no talking on your cell phone!

How to Enter: Look for the lantern on the mural painted across the street from Big Star.

9. BordelWicker Park, 1721 W. Division St.

With an unmarked door, this hidden treasure takes a little more searching.  Perched above the Spanish Tapas restaurant, Black Bull, lies Bordel. Once you find your way inside, this cocktail lounge is a refreshing change of pace from the streets below, and a beautiful interior to enjoy some cocktails and the live entertainment, including burlesque shows and flamenco dancing.

How to Enter: Go through the door to the right of Black Bull, go up the stairs, then enter the door on your left.

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Wrigley Field Speakeasies

10. Room 13 - Lakeview, 3222 N. Sheffield Ave.

The number 13 is accompanied with some superstition, especially in the hotel industry.  The Old Inn Chicago takes advantage of this, and has their own 1920’s speakeasy bar named Room 13.  This secret bar is hard to enter though, as it requires an ever changing password to enter. Hotel guests and members will receive an invitation to Room 13. Serving traditional prohibition alcohol, such as whiskey and gin, this space really plays the part.

How to Enter: Apply for a membership to the the Old Chicago Inn, or stay at the Inn as a guest. The entrance is found in the all to the left of the Inn on Sheffield and Belmont.  Look for the red-lit gate with an “RM-13” logo.

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About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: May 10th, 2024
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