food & drink · music & nightlife ·
Published August 3, 2023
Chicago's Best Hidden Speakeasies
Throw it back to Prohibition days at these legendary Chicago hotspots. 🍸
by Chicago Bucket List
Chicago has a storied history with speakeasies stretching back to Prohibition when some of the country’s most notorious gangsters ran the city and opened secret spots throughout the city to keep the party going.
Speakeasies are no longer a necessity for revelers looking for a good time, but they remain a thriving part of Chicago’s nightlife scene. These days, you’ll find hotspots offering everything from legitimate Prohibition-era throwbacks to new spots offering cutting-edge cocktails and creative themes to transport you anywhere from Tokyo to a tropical paradise.
A password might not be required to get in, but we guarantee that these in-the-know spots will show you a one-of-a-kind night out in Chicago.
25 Secret Speakeasies You Need to Check Out in Chicago
Nestled in Wicker Park, you'll find a record shop with a wide selection of vinyl and a listening booth. If you keep going, though, you'll step through another door that leads to a cocktail bar with live performances and vinyl DJ sets over Hi-Fi Italian sound. Grab yourself a cocktail and sink into a plush, emerald booth while listening to live jazz and taking in the exposed brick and walls lined with records.
Where: 1939 W North Ave. Chicago, IL
The Violet Hour
If you’ve visited Violet Hour before but can’t seem to find it this time around, your eyes aren’t playing tricks on you. It’s intentional—Violet Hour’s exterior features an ever-changing mural facade that features different artists. No one would blame you for not realizing there’s a bar tucked away behind the art!
Once inside, enjoy a list of James Beard-award-winning prohibition-style cocktails that change seasonally, plus a menu of small plates, all served in an elegantly appointed space.
How to get in: Find the doorknob hidden in the wall of the mural (hint: let the light illuminate your way!) to step into this secret world.
Where: 1520 N Damen Ave, Chicago, IL
For more information on The Violet Hour.
The Library at Gilt Bar
After a decadent meal in the playfully elegant Gilt Bar, head downstairs to finish the evening with a nightcap in a booth at The Library. This romantic space, lined with books (of course) and flickering candles, will welcome you with cushy red velvet booths to sink into. With masterfully mixed cocktails and an extensive wine list, it’s a great place to while away an evening.
Don’t forget to stop by the photo booth to document your evening out. Leave a strip for the wall, and take one with you for the memories.
How to get in: Head down the hallway lined with photos and find the unmarked door on the right, which will lead you down into this intimate cocktail den.
Where: 230 W Kinzie St, Chicago, IL
For more information on the Library at Gilt Bar.
Are we in Chicago, or are we in Tokyo? When you step into Booze Box, an intimate space tucked under sushiDOKKU in West Loop, it’s hard to be sure! Booze Box transports guests straight to Japan with Izakaya-style street food-inspired small plates and an extensive list of creative cocktails, plus sake and Japanese whisky, of course.
The space has a lively atmosphere lit by red lanterns and hip-hop beats setting the ambiance for this killer late-night spot.
How to get in: Find the bamboo-lined door next to sushiDOKKU – the glowing red arrow will lead the way.
Where: 823 W Randolph St, Chicago, IL
For more information on Booze Box.
The Bamboo Room
If you’re looking for a tropical paradise to escape the bitter Chicago cold without boarding a plane, we’ve got you. Three Dots and a Dash draws crowds of its own, but it’s worth visiting its bar-within-a-bar, The Bamboo Room. With lush tropical foliage and glowing pineapple lamps, the cozy 22-seat room mirrors the aesthetic of the larger bar but with a calmer ambiance—you’ll feel like you’re running on island time when you step inside.
Rum is the star of the show at The Bamboo Room, where the mixologists serve up a variety of libations featuring some of the world’s most exclusive and unique rums.
How to get in: Head past the velvet ropes inside Three Dots and a Dash to be transported to this tropical paradise.
Where: 435 N Clark St, Chicago, IL
For more information on The Bamboo Room.
If you want to get into this exclusive speakeasy, it’ll cost you. The price? Either a stay at the historic Old Chicago Inn or a yearly membership for those aspiring to become regulars. But it’s worth the hassle—once inside, you’ll find yourself sipping on a bevy of Jazz Age-inspired cocktails whipped up by the joint’s resident bartenders, served with a side of Prohibition history and anecdotes.
How to get in: Find the alleyway entrance just to the left of the Old Chicago Inn on Sheffield and Belmont – but remember, you’ll need the secret password to get in.
Where: 3222 N Sheffield Ave, Chicago, IL
For more information on Room 13.
Experience The Bassment, a live music cocktail lounge located below The Hampton Social! Enjoy live music while savoring their handcrafted cocktails in an unforgettable atmosphere. Guests enter through a secret door, and the whole place has decor that's styled with the 1960's British Invasion movement in mind.
How to get in: Located below The Hampton Social. Reservations required. Business casual dress code.
Where: 353 W Hubbard St, Chicago, IL 60654
For more information on The Bassment.
Exclusivity is the name of the game at this tiny eight-seat microbar tucked into the Chicago Athletic Association hotel. This intimate spot is a bonafide holdover from Prohibition days when members of the exclusive athletic club used to stop in for glasses of “milk” mixed with alcohol to evade the watchful eyes of policemen.
Nowadays, you’ll find an extensive list of spirits, including a selection of some of the rarest vintage spirits in the country. For those looking for a one-of-a-kind bespoke cocktail experience with exquisite craftsmanship, there is no comparison.
How to get in: Reservations required. Look for the ornate stained glass doors on the second floor to find this cozy nook.
Where: 12 S Michigan Ave, Chicago, IL
For more information on Milk Room.
If you’re in the mood for a mystery, The Drifter is the place to go. The bar has a stacked lineup of 100 cocktails written on tarot cards, and each night, their team of bartenders chooses just a handful of cards from the deck. You never know what will be on the menu that evening!
This spot also hosts regular jazz and burlesque performances, and the most adventurous visitors can opt for a fortune cookie surprise. For $10, you receive a fortune cookie, and the bartenders will craft you whatever drink is listed inside!
How to get in: Head through Green Door Tavern, follow the staircase downstairs and look for the bookshelf with oddities to find the hidden door.
Where: 676-8 N Orleans St, Chicago, IL
For more information on The Drifter.
Chicago Magic Lounge
The Chicago Magic Lounge is helping to usher in a new wave of magic bars in Chicago, carrying on a longstanding city tradition of close-up magic and bringing lighthearted fun to an evening out. While most speakeasies are known for close quarters, inside this sprawling space, you’ll find the Magic Bar, the Blackstone Cabaret for larger performances, and the 654 Room, focused exclusively on close-up magic.
Of course, at a venue dedicated to sleights of hand, you have to expect the secret entrance is going to be amazing—and it does not disappoint.
How to get in: No dirty laundry here, but you’ll need to choose the right washing machine in the laundromat up front to make your way inside.
Where: 5050 North Clark Street, Chicago, IL
For more information on the Chicago Magic Lounge.
Type in “the Alderman” on Google, and you’ll come away with pages of local councilmen but scarce information on this next spot on our list. Yet, if you can find it, this intimate speakeasy tucked in the back of the new Pilsen Yards restaurant is serving up some of the best cocktails in the city at the moment.
With a cocktail menu curated by award-winning beverage director Lance Bowman, who rotates half of the selections every two months, there’s always something new to pique your interest.
How to get in: Look for the glowing red sign at the back of Pilsen Yards.
Where: 1163 W 18th St, Chicago, IL
For more information on The Alderman.
Looks can be deceiving at this clandestine cocktail lounge. When you walk up to this modern barbershop tucked inside Fulton Market, you’ll find yourself wondering if you’re in the right place. Head inside and through a discreet door in the back to find a casual and lively rec room-inspired space with luxurious leather sofas, wood-paneled walls, and live music.
Just like its sister locations in New York and Los Angeles, the Chicago outpost of the Blind Barber serves up carefully crafted cocktails alongside decadent plates.
How to get in: Find the discreet door at the back of the barbershop and head through the velvet curtains to enter the hippest “rec room” we’ve ever seen.
Where: 948 W Fulton Market, Chicago 60607
For more information on Blind Barber.
The vibe is Paris’ Belle Epoque meets Chicago’s Prohibition Era at this happening bohemian speakeasy and cabaret. You’ll feel like you stepped straight into the Latin Quarter at this bar, which features a rotating cast of jazz musicians, burlesque performers, fire-eaters, magicians, cabaret dancers, comedians, and more.
Absolutely don’t miss the famous punch, served in true Prohibition-style Royal Albert tea sets. As the old saying goes: where there’s punch, there’s always a party!
How to get in: Open the unmarked door next to Black Bull and head up the red stairwell.
Where: 1721 W Division St, Chicago, IL
For more information on Bordel.
Pull up a leather bar stool in the warm, brick-walled lounge at Meadowlark in Logan Square. The 30-seat cocktail haven may be roomy, but it still manages to feel cozy and full of vintage Chicago charm. Plus, it serves delicious bar food—the empanadas are a must-try—along with the original cocktails.
How to get in: Enter through the unmarked door in the back alley of Lardon and Union.
Where: 2812 W Palmer St, Chicago, IL
More information on Meadowlark.
Hidden inside the Hoxton is a teal blue wrap-around bar serving brightly colored drinks in the tropically-infused, upscale Lazy Bird. The spot is soundtracked with live music from jazz, to rock, to soul every Thursday, Friday, and Saturday night! The only hard thing in this hidden oasis might be choosing from their excellent 52 classic cocktail list.
How to get in: Located in the cellar level of The Hoxton.
Where: 200 N Green St, Chicago, IL
More information on Lazy Bird.
The electric Momotaro Izakaya takes guests back to the post-war black market in Tokyo. The pub is lined with street signs lit by red Japanese lanterns and serves sake and Japanese whiskey to its few dozen seats, along with sashimi, sushi, and ramen. Try the A5 Cup Noodle for a fun “top ramen” presentation.
How to get in: Located underneath Momotaro restaurant. Enter on the street side of the restaurant, where there is a door sign that says “Bar” and “Izakaya” painted on the door.
Where: 820 W Lake St, Lower Level Chicago IL
More information on Momotaro Izakaya.
Mile High Cocktail Club
Perched in the clouds—that is, on the 46th floor of the Four Seasons—this cocktail club will show you the wonders of the world through themed drinks. The “highest speakeasy in Chicago” is lavishly designed to emulate an Orient Express railcar. Visitors begin in a pre-departure lounge and move into the luxe Cocktail Club where they can get a side of epic views with a bespoke beverage.
How to get in: Reservations are required and start at $65-125 per person.
Where: 120 E Delaware PL Chicago IL
More information on Mile High Cocktail Club.
Although it's the first speakeasy to open in Chicago’s Chinatown, Nine Bar is steeped in neighborhood history and located in the decades-old locally loved restaurant, Moon Palace. The elegant bar serves Asian liquor and classic American cocktails but really shows out with its fusion cocktails, like the Calpico, a mai tai with Chinese cookie orgeat syrup.
How to get in: Head into the Moon Palace Express kitchen and follow the neon accent lights down a dark narrow hallway.
Where: 216 W Cermak Rd, Chicago, IL
For more information on Nine Bar.
Sip rare, antique spirits and chef-designed bites in the ultra-refined Office, located behind a locked door directly below the swanky restaurant The Aviary. Two bartenders will mix personalized drinks with ancient alcohols on the spot, which helps this spot earn its descriptor as the hardest speakeasy to get into in Chicago. Seriously—the drinks are so complex, there’s a dedicated Ice Chef who makes over thirty different types of ice to best complement each drink.
How to get in: Since The Office is notoriously hard to get into, we recommend booking a paid experience online, then going to The Aviary and asking your server if it's possible to go downstairs. But rumor has it you may get lucky with a spontaneous invitation while at dinner at the Aviary.
Where: 955 W Fulton Market, Chicago, IL
More information on The Office.
Logan Square’s Soif (meaning “thirst” in French) is a romantically-lit brasserie-style speakeasy with red velvet booths and vintage wood and marble tables, giving the feeling guests are suddenly in a warm Parisian salon. In fact, the wine menu focuses on French gems and different champagnes, along with a rare and stellar collection of German beers.
How to get in: A door inside Testaccio is open until 7 PM, but after that, the only entrance is located down an exterior stairwell below Testaccio on Altgeld St, glowing with a neon "Soif" sign.
Where: 2456 N California Ave, Chicago, IL
More information on Soif.
Underneath the Moonflower—a sandwich and cocktail bar full of deeply creative ingredients and globally-inspired drinks and bites, lies another hidden, darker botanical gem: Nightshade. The cocktail menu is steeped in bright notes of grapefruit, cucumber, and botanist Gin—plus really cool shaved ice cocktails and shaved ice shots.
How to get in: Look for the back door in Moonflower, with a flashing red light.
Where: 4359 N Milwaukee Ave, Chicago IL
More information on Nightshade.
There’s a subterranean speakeasy bar in Jaleo Chicago from world-famous Chef José Andrés that no foodie wants to miss. Pigtail serves ibérico pork and bespoke cocktails in a sultry LED-lit lounge. The Spanish tapas menu is filled with delicious churros, house-ground pork and steam buns, bone-in jamón, and many more delights—all along with a primo cocktail and Spanish Sherry drink list.
How to get in: Guests enter through the Jaleo entrance on Illinois Street
Where: 500 N. Clark St, Chicago IL
More information on Pigtail.
It’s not a night out without sharing a punch bowl, right? Head to Punch House, hidden below landmark music venue Thalia Hall, for the ultimate fix. The basement bar is aptly decorated to look like your childhood buddy’s downstairs living room, has nightly “song selectors,” serves a variety of boozy punch by the glass/carafé/bowl, and sells bar snacks, tasty sandwiches, and ice cream to boot! In other words, you'll be living out your rebellious teen dreams here.
How to get in: Enter through an unmarked staircase in the front restaurant area of Thalia Hall or behind a single unmarked black door in the back.
Where: 1227 W 18th St, Chicago, IL
More information on Punch House.
Seeking a little Tex-Mex in midwestern Chicago? Start at the sunny taco bar Lonesome Rose, then head downstairs to a moody, vintage, and black-walled, 40-seat cocktail bar. The drinks-only menu is spirit-forward, reminiscent of the borderlands (Northern Mexico and Southwestern U.S.), and includes an excellent assortment of mezcal.
How to get in: Check the alley outside Lonesome Rose and head down the building’s back steps. Look for a small black “Golden Teardrops” sign.
Where: 2101 N California Ave, Chicago, IL
More information on Golden Teardrops.
The Franklin Room
This speakeasy is as classic as it sounds: The Franklin Room celebrates all that’s great about the American tavern, serving classic cocktails along with meat and seafood dinner plates. The drink menu favors whiskey (there’s even a Whiskey Keep Club with a members-only menu) and a wine and beer menu that focuses on indie distillers and limited-edition rare releases.
How to get in: This one isn't so hidden—look for the street-facing sign above the door.
Where: 222 W Adams St.
More information on the Franklin Room.
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