Chicago's Hidden Speakeasies

Chicago Bucket List By Chicago Bucket List

Where magic meets cocktails (and a ton of hidden doors). 🍸


Something special happens when you walk into your favorite bakery, but instead of ordering that gorgeous everything bagel you've been pining after, you walk straight through to a secret bar hidden downstairs.

By our calculations, speakeasies are the most effective way to impress a date or your group of friends. Not only will you look like the most knowledgable kid in town, you'll also get to experience another era. Japan, Paris, or even Prohibition time Chicago - take your pick and saddle up for some strong vibes, and even stronger cocktails. 

 
 
 
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Violet Hour

One of our favorite speakeasy bars in the city. Walking down Damen, you could have easily walked past this large wall numerous times without knowing that there is a secret bar hidden behind it. On par with the neighborhoods murals and graffiti culture, there is a door hidden behind a colorful wall. Once you walk in, you'll feel transported into an Alice in Wonderland fantasy of sorts, where mixologists take care of your every need. But remember, no cell phones allowed.   

How to get in: If there isn't a large line to give it away, play a game of Where's Waldo and locate the door knob on the large mural on Damen. 
Where: 1520 N Damen Ave, Chicago, IL 60622 | Wicker Park 

For more information and reservations.

 
 
 
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The Library at Gilt Bar

After stuffing your face at the cozy Gilt Bar, best recommended with a side of burnt brussel sprouts, you may be searching for a nightcap. Oh, where could you go?

Make your way downstairs, past the photo booth (where you'll most ultimately make a pit stop later after a bottle of red), through a long hall filled photos (where you'll leave your mark in speakeasy history), to The Library. This dimly-lit room, lined with bookshelves and wooden moldings, will welcome you with arms wide open and cushy velvet booths to sink into. With a stacked cocktail menu and wine list, last call will come sooner than you think.

How to get in: Down the stairs you go, below Gilt Bar. 
Where: 230 W Kinzie St, Chicago, IL 60654 | River North  

For more information and reservations.

 
 
 
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The Ladies Room

First of all, do yourself a favor and stop by Fat Rice Bakery, the egg tarts are divine and may even treat you better than the ones in Portugal. Okay, back on track. Once you have an egg tart in hand, walk through the curtains near the bathroom to find The Ladies Room (pun intended).

The ambiance hits you like someone flipping the lights on after a dark movie - but in reverse. This reservations-only spot feels straight out of the Macau red light district. Once your eyes have adjusted to the dim lights, you'll notice the pin up posters covering the walls and the intimate space that will take you back into the early 20th-century for some unconventional cocktails.

How to get in: Enter the bakery and walk towards the bathroom where you'll find a curtain to the bar. 
Where: 2957 W Diversey Ave, Chicago, IL 60647 | Logan Square 

For more information and reservations.

 
 
 
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Milk Room 

It may come as a surprise to learn that the Cindy's Rooftop isn't the only hopping spot inside the Chicago Athletic Association. What was once a speakeasy used by members during Prohibition, is now an eight-seated microbar found on the second floor of the hotel. Make a reservation and enjoy some extremely rare liquors that could run dry by the end of the year, giving ‘last call’ an entirely new meaning.

How to get in: 2nd floor of The Chicago Athletic Association. 
Where: 12 S Michigan Ave, Chicago, IL 60603 | The Loop

For more information and reservations.

 
 
 
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Booze Box

*Siri, please define Izakaya* - Japanese bar in which a variety of small, typically inexpensive, dishes and snacks are served to accompany the alcoholic drinks.

Located beneath sushiDOKKU, Booze Box is a Japanese small-dish and drinking establishment, Japanese Izakaya-style small plates and street food. A space lit by red lanterns and surrounded by wood paneling, bring your friends by and define Izakaya for them while sipping back some saki. Impressed yet?  

How to get in: Enter through the back alley door of its parent restaurant, sushiDOKKU.
Where: 823 W Randolph St, Chicago, IL 60607 | West Loop

For more information and reservations.

 
 
 
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The Bamboo Room

From the team that brought you the ever popular Three Dots and a Dash, comes Bamboo Room. The "bar-within-a-bar" holds with a calmer environment than it's boisterous counterpart. The 22-seat bar room mirrors the tiki aesthetic of Three Dots but focuses on a calm ambiance and rum, mon. The minute you walk in, you'll get transported to a tropical place that serves some of the country's most high-end and rare rums. A reservation is suggested. 

How to get in: Look for the Tiki torch and velvet rope in the alley behind the building on Clark Street.
Where435 N Clark St, Chicago, IL 60654 | River North

For more information and reservations.

 
 
 
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The Drifter

If you're looking for an authentic speakeasy experience (and by authentic we don't mean a dimly lit room with a speakeasy tag) then head over to The Drifter. Located in an authentic (let us say the word authentic once more) 20s-era speakeasy, Green Door Tavern brings you 100 years worth of drifters. Grab a tarot card as a cocktail menu and find a seat in front of the massive FDR portrait. Big brother will be watching. 

How to get in: Walk through Green Door Tavern, head downstairs and enter through the wooden door that’s next to the restrooms - knock and he’ll let you in.
Where: 676-8 N Orleans St, Chicago, IL 60654 | River North

For more information and reservations.

 
 
 
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Room 13

You want in? It's gonna cost ya. A stay at the Old Chicago Inn or a payment for a yearly membership.

This Prohibition era-inspired speakeasy is no easy feat if you just want to sip on a cocktail. To get in, you'll look for the discreet alleyway entrance just to the left of the Old Chicago Inn on Sheffield and Belmont. Once located, whisper the ever-changing password to the man at the door, but halt - if you aren't a guest at the hotel or a guest of a member, you shall be turned away. The good news, if you ever find yourself inside, is you'll enjoy a resident bartender with a world's knowledge of cocktails and cultural anecdotes. Proper dress required. 

How to get in: Alleyway entrance just to the left of the Old Chicago Inn on Sheffield and Belmont. 
Where: 3222 N Sheffield Ave, Chicago, IL 60657 | Lakeview

For more information.

 
 
 
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The Office 

Just when you thought you couldn't love Grant Achatz any more, he opens a speakeasy. Beneath his innovative cocktail lounge, The Aviary, comes a speakeasy that stands in contrast to his current repertoire of restaurants. With the theatrics of serving food removed, you strip The Office down to its core of great ambiance and even greater cocktails. If you need to use the restroom, be sure to grab the key, otherwise you may be locked out with the plebeians on the outside (totally kidding, we love you Grant). 

How to get in: Through The Aviary, you'll find a locked door that will require someone to let you in. 
Where: 955 W Fulton Market, Chicago, IL 60607 | Fulton Market 

For more information and reservations.

 
 
 
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Janitors Closet 

What was once a janitors closet is now a janitors closet with a bartender. Here you'll find all the tools necessary for a good night like wrenches, power tools, tequila, and a 15-seat bar. Your friends might think you've lost it the minute you open a janitors closet for a night out, but they will be ecstatic to see the custodian behind the bar - trust us. 

How to get in: Located within River North boutique hotel FieldHouse Jones, this speakeasy is in the most literal sense, a janitor's closet. 
Where12 W Chestnut St, Chicago, IL 60610 | River North 

For more information and reservations.

 
 
 
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Bordel

Fringe, lights, ACTION! From the restaurant group that brought you the majestic Beatnik on the River, is Bordel. They've set out, once again, to transport you into a different period - Paris' Belle Époque mixed with Chicago's Prohibition Era. The bar features a rotating cast of jazz musicians, burlesque performers, magicians, cabaret dancers, comedians, *takes deep breath* and more. The velvet-lined chairs, bohemian styled wallpaper, and nipple tassles are sure to leave you with a night you won't forget...

How to find it: Above Black Bull via an unmarked door and a red stairwell.
Where: 1721 W Division St, Chicago, IL 60622 | Wicker Park 

For more information and reservations.

 

 


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