If you thought Chicago’s nightlife was limited to trendy rooftop bars and deep-dish pizza joints, think again. Hidden behind unmarked doors, tucked down shadowy alleyways, and nestled below bustling restaurants lies a whole other world. One filled with flickering candles, vintage glassware, and the best cocktails you’ll ever have in your life.
From tiki-inspired hideaways with flaming rum cocktails to moody underground clubs where the only menu is a tarot card, Chicago’s speakeasies and hidden bars offer a nightlife scene unlike any other. Whether you’re in it for the innovative cocktails, the secretive ambiance, or the thrill of finding the entrance in the first place, these sparkling gems are guaranteed to shake up your night.
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The Drifter
The self-acclaimed “best speakeasy bar in Chicago”, the Drifter does things a little differently than other bars in the city. Instead of a set cocktail menu, this 1920s-era bar boasts more than 100 cocktails in rotation. Each night, the team chooses a number of cards from a tarot deck, each of which has a cocktail listed on it. This unique approach keeps things fresh and exciting, no matter how many times you’ve been before!
Between Wednesday and Friday there’s live entertainment from 7pm until midnight. Most sets are pretty short (around 5-15 minutes) and vary from burlesque shows to magicians and standup comedians. They’re the perfect thing to break up the evening and add a touch of old-school intrigue to your night.
It’s worth knowing that an $8 cover charge per person is added onto the bill and there’s no flash photography or cell phone flashlights allowed. This may seem a little harsh, but it helps keep the speakeasy vibe alive.
How to get there: Walk into the Green Door Tavern and take the stairs down into the basement.
Blind Barber
Don’t be fooled by this ordinary barbershop. By day, it’s a great place for a haircut or beard trim. But by night, the Blind Barber transforms into one of the coolest hidden bars in Chicago. Dark polished wood, exposed brickwork, and low mood lighting combine to create the perfect speakeasy atmosphere. There’s a DJ at the back of the room and, although the music can get a little loud, it creates lowkey party vibes.
Happy hour runs from 5pm to 7pm, Tuesday through Friday, when you can get cheap drinks for $5-$10. But even full-priced cocktails start at $15, making this place reasonable value for money for Chicago.
The Blind Barber is open from 9.30am to 2am. If you’re planning on getting a trim while you’re there, you can enjoy a drink in the bar before or after. A lot of the time the barbers will even ask you if you want a drink while getting your haircut!
How to get there: Walk into the Blind Barber barbershop and introduce yourself to the barbers, telling them if you have a reservation or you’re a walk-in. They’ll direct you to the door.
Three Dots and a Dash
Offering a tropical twist on the classic speakeasy vibe, Three Dots and a Dash is a 1940s-inspired tiki bar. Unlike the iconic sidecar and old fashioned cocktails that you get at classic speakeasies, this vibrant island-inspired venue serves over-the-top cocktails made with exotic fruits, fresh spices, and creative spirits made in-house daily.
The group drinks are the stars of the show — tropical cauldrons loaded with exotic flavors like passionfruit, guava, and pomegranate. The presentation is sensational, with one-of-a-kind glasses, fresh flowers, and slices of fruit that somehow act as candles.
Three Dots and a Dash has a secret — the Bamboo Room. A bar within a bar, this exclusive space serves sophisticated and innovative rum-based cocktails along with incredible rum flights. It’s a great place to start off early in the evening when the place is quiet and you can ask the bartender to make you something special. Move onto the main Three Dots and a Dash bar when things start to get lively.
How to get there: Turn into the alley on West Hubbard Street next to Firecakes Donuts. Open the doorway with the Three Dots and a Dash sign above it and walk through a dimly lit, jungle-meets-voodoo corridor painted with skulls, pirate ships, shrunken heads, and giant clams.
Nine Bar
Hidden within the Moon Palace Express restaurant, Nine Bar offers you the best of both worlds. It successfully honors Chinatown’s rich history while still managing to embrace today’s modern cocktail scene. The drink menu is overflowing with Asian craft cocktails that you’ll struggle to find anywhere else in the city. Ingredients like lychee, sichuan peppercorns, green tea, and pickled daikon make the drinks here seriously pop.
Nine Bar isn’t just a great place to grab a drink — it’s also a fantastic spot for a light dinner. The food menu boasts more Asian-inspired delights, from mapo hot fries with chilli pork sauce and wok-fried salt and pepper wings to grilled cheese sandwiches with housemade kimchi and bruleed toast with five spice condensed coconut milk.
Visit during the week if you want somewhere quiet you can chat or on the weekend for DJ sets and a more energetic, late-night vibe.
How to get there: Walk to the entrance of the Moon Palace Express restaurant. If you see a bouncer, you’re in the right spot.
The Alderman
One of the smallest speakeasies in Chicago, the Alderman has room for just 16 people, making reservations practically mandatory. Here you’ll find classic cocktails, like espresso martinis, strawberry daiquiris, and whiskey sours on the menu, each of which has a special twist that elevates the drink to a whole new level.
The Alderman is really dark and moody — in a good way. There are no bright lights. The whole place is lit by subtle flickering candles and dim ceiling lights, creating the perfect setting for a romantic date night. If you’re feeling hungry, extend your night by dining at the Pilsen Yards which is owned by the same people.
Most speakeasies in Chicago open at around 5pm at the earliest. The Alderman opens at 3pm on the weekend, making it a fantastic spot for an early cocktail. Stop by on a Sunday and you’ll get a whopping 35% off your bill.
How to get there: Walk into Pilsen Yards. The Alderman is hidden behind a secret wall. If you can’t spot it yourself, a member of staff will reveal it to you.
Golden Teardrops
Hidden away inside the basement of the Lonesome Rose, Golden Teardrops looks like a modern, industrial nightclub at first glance. But the more you look around, the more the bar’s quirky character comes out. A curious “Weddings & Funerals” neon sign, a taxidermy racoon rowing a canoe, and a single cowboy boot dangling behind the bar are among the hidden-in-plain-sight decorations.
Here you can choose from eight creative riffs on classic cocktails, where carefully-selected high-proof spirits shine. The menu changes every three months, giving you plenty of chances to return for a new sip. Despite being fairly large for a speakeasy (the venue has 40 seats), the low ceiling, black walls, and vintage lighting create a sultry, moody atmosphere.
The Lonesome Rose upstairs is an amazing place for fun Mexican fare. Their tacos are superb, with the baja fish taco being a solid favorite.
How to get there: Find the Lonesome Rose and walk around the corner until you’re on West Henry Court. Look for the black metallic stairs leading down on your left.
The Booze Box
One of the best-hidden speakeasies in Chicago, the Booze Box doesn’t have a website, social media channels, or even a location on Google Maps. This ultra-exclusive spot is hidden in the basement of the Michelin Star restaurant, Sushi Dokku on West Randolph Street. Here the gentle red lighting, lowkey DJ sets and creative Japanese cocktails come together to create a funky underground Tokyo vibe that feels effortlessly cool and intimate.
It is a little bit on the small side, so get there early or make reservations if you don’t want to be left standing.
Despite its name, the Booze Box isn’t just for drinks. You can order anything from the remarkably comprehensive Sushi Dokku menu and enjoy it here. The tuna tataki with Japanese pickles and dragon rolls with tempura shrimp and eel are incredible.
How to get there: Walk into the alley to the side of Sushi Dokku and look for the red neon arrow pointing the way. Alternatively, you can walk into Sushi Dokku, head straight behind the bar, and walk down a maintenance stairwell.
Fox Bar
Hidden on the mezzanine floor of Soho House, Fox Bar is an unassuming bar that serves up a fantastic seasonal menu of craft cocktails. The ingredients are carefully chosen to suit the time of year. Think cinnamon and pumpkin in fall — citrus and mint in spring. There’s also a decent choice of beers available year-round.
Fox bar feels pretty spacious compared to others on this list. There’s one large table in the center for big groups, with smaller tables for couples dotted around it, plus a limited number of seats at the bar.
One of my favorite things about this spot is that it doesn’t take reservations. It accepts people on a first come, first served basis. The friendliness of the staff, relaxed vibe, and edgy decor make this spot feel less like a speakeasy and more like an exclusive members club.
How to get there: Walk into the Soho House and look for a big fox painting on the wall by the staircase on your right. Go up the stars and walk through the door with “Bar Service Only” on it.
The Untitled Supper Club
For something bigger and bolder, consider the Untitled Supper Club. Boasting a classic 1920s Prohibition era design, this popular hotspot is less of a classic speakeasy and more of an entertainment and dining venue. It covers a huge space with plenty of seating, making reservations optional. Plush red walls, velvet-covered seats, and art-deco lighting will make you feel like you’re in a genuine speakeasy from 100 years ago.
There’s live entertainment every Wednesday through Saturday in the form of music tributes, burlesque shows, and acrobatic performances. There’s a small surcharge for tables within the main stage area, but the entertainment is so superb that it’s worth it.
The food menu is bursting with popular favorites, like crispy calamari, creamy burrata, juicy New York strip, and loaded smashburgers. There’s even a raw bar selection if you’re feeling fancy. The cocktail menu is small but perfectly curated, with all the classics, as well as some original creations.
If you’re watching your spending, visit between Tuesday and Friday at 5pm for happy hour.
How to get there: Walk along West Kinzie Street and look for a plain black door with a bouncer.
The Library
Tucked away in the basement of the Gilt Bar, the Library is the stuff book lovers’ dreams are made of. You walk through a dramatic hallway covered with black and white photobooth pictures of people (feel free to add your own!) to a non-descript door that opens out to one of the most beautiful speakeasies in the city.
Wine-colored wood-paneled walls, wrap-around velvet sofas, low retro lighting, and, of course, walls of books, create the ideal setting to relax and enjoy a good drink. The comprehensive drinks menu is filled with classic American cocktails like martinis and old fashions, as well as beers, wines, and spirits.
The food served in the Gilt Bar is also available to enjoy in the Library. So make an evening of it and enjoy the literary-chic atmosphere along with a double wagyu cheeseburger, housemade vodka rigatoni, or honey-peppered king salmon. Reservations open up each Wednesday for the following week, so get in fast.
How to get there: Walk into the Gilt Bar and ask to be seated in the Library.
There you have it! The best speakeasies and hidden bars in Chicago. Do you have a favorite that we’ve missed? Tell us about it and we’ll add it to our list!
