I’m going to let you in on something: some of the best nights I’ve had in Chicago started with walking past what looked like a laundromat, a record shop, or a completely blank wall — and ending up in a candlelit basement with a cocktail I didn’t even know I wanted. That’s the magic of Chicago’s speakeasy scene.
This city basically invented the modern speakeasy during Prohibition (thanks, Al Capone), and that energy is very much alive today. The difference is you don’t need to know a gangster to get in — you just need to know where to look. And that’s exactly what I’m here for.
🥃 Here’s the Deal
Chicago has over 20 speakeasies and hidden bars, but the 15 on this list are the ones actually worth the hunt. The best overall experience is The Drifter (River North) for its tarot-card cocktail menu and live entertainment. For the most hidden entrance, try Booze Box in the West Loop — no website, no signage, just a red neon arrow in an alley. For romance, The Alderman in Pilsen seats just 16 people by candlelight. And for pure spectacle, Chicago Magic Lounge hides inside what looks like a laundromat. Most cocktails run $16–$22, reservations are recommended everywhere, and smart casual dress is the move.
🏆 Quick Picks
- 🥇 Best Overall: The Drifter — tarot card menus, live entertainment, actual Prohibition history
- 💑 Most Romantic: The Alderman — 16 seats, candlelit, Pilsen
- 🔍 Hardest to Find: Booze Box — no website, no Google listing, follow the red arrow
- 🎭 Best Entertainment: Chicago Magic Lounge — live magic shows + cocktails
- 💃 Best for a Group Night Out: Bordel — burlesque, cabaret, craft cocktails
- 🌴 Best Tropical Vibes: Three Dots and a Dash — tiki cocktails in a hidden basement
- 🆕 Best New Addition: Club X — opened Dec 2024, Prohibition-era building, molecular cocktails
The Best Chicago Speakeasies & Hidden Bars
1. The Drifter
Okay, I’m putting this one first because it genuinely has everything you want in a speakeasy — and it’s housed inside a building that was an actual Prohibition-era speakeasy. The Drifter is hidden in the basement of Green Door Tavern, one of the only wooden buildings to survive the Great Chicago Fire (built 1872 — you can still see the building leaning slightly from settling). During Prohibition, a green door meant a speakeasy was inside. Walk through the tavern, find the staircase in the back, go down, and look for the entrance. It’s not obvious, which is the point.
Once you’re in, the experience is unlike anything else in the city. Instead of a regular menu, your cocktails are served from a rotating deck of custom tarot cards — each card is a different drink. The bartenders shuffle through over 100 cocktails and present a different selection each night. On top of that, there’s live entertainment most nights — think burlesque dancers, contortionists, belly dancers, and close-up magic. It’s theatrical, intimate (capacity is only 37), and genuinely fun. This is the speakeasy I bring every out-of-town friend to.
💡 Pro Tip: The Drifter fills up fast and the capacity is tiny. Book through Tock in advance, especially for Friday and Saturday. If you go on a Wednesday or Thursday, you’ll have a much easier time getting in.
2. The Alderman
If you want to feel like you’ve discovered something truly special, The Alderman is it. There are only 16 seats in the entire place, and it’s tucked inside Pilsen Yards (a great Mexican restaurant with a big outdoor patio). Look for the neon sign that just says “The Alderman” — it’s not exactly hidden, but you absolutely have to know it’s there to find it.
Inside, it’s dark in the best way. Flickering candles, dim ceiling lights, and a carefully curated cocktail menu that changes regularly. The bartenders here are incredible — they know every drink inside and out and love talking you through the menu. What I really appreciate is that the cocktails feel elevated without being pretentious. You can get a beautifully crafted espresso martini or a whiskey sour that’s been given a creative twist, and it all just works. This is my top pick for a date night or a quiet evening where you actually want to talk to the person you’re with.
💡 Pro Tip: Come on a Sunday and you’ll get 35% off your bill. The Alderman also opens at 3pm on weekends, making it one of the few speakeasies where you can grab an early afternoon cocktail.
3. Chicago Magic Lounge
Here’s where it gets really fun. From the outside, Chicago Magic Lounge looks like a laundromat. Seriously — there are washing machines and dryers and fluorescent lighting and everything. But find the right “machine” and you’ll walk through into one of the coolest hidden bars in the city.
The main attraction here is the magic, and it’s legit. This isn’t a tourist trap — these are professional magicians performing close-up sleight-of-hand right at your table and full stage shows in the theater. The cocktails are well-crafted, there are small plates, and the whole vibe feels like you’ve stepped into a 1920s magic club. Even if you’re not a “magic person,” I promise you’ll leave here grinning. It’s the kind of place where everyone in your group will be talking about it for weeks.
If you just want to pop in for a drink without the full show, you can hang out in the front lounge where magicians do tableside tricks. But I’d recommend booking the full experience at least once.
4. Booze Box
This is the one the locals don’t want me telling you about. Booze Box has no website of its own, no social media page, and for a long time didn’t even show up on Google Maps. It’s hidden in the basement of Sushi Dokku on Randolph Street in the West Loop, and finding it is half the fun.
Here’s how to get in: walk into the alley behind Sushi Dokku and look for the red neon arrow pointing toward a door. Head down what looks like a maintenance stairwell, and suddenly you’re in this moody, red-lit underground lounge with DJ sets, Japanese cocktails, and some of the best sushi in the neighborhood. The vibe is very underground Tokyo — intimate, cool, effortlessly stylish. You can order the full Sushi Dokku menu down here, and I highly recommend the lamb chops and the dressed nigiri bites alongside your cocktails.
💡 Pro Tip: It gets packed on Friday nights by 7pm. Show up early or make a reservation — and try to grab one of the booths along the edges for the best experience. DJs spin live on Friday and Saturday nights.
5. Dorian’s
Walk past Dorian’s during the day and you’d swear it’s just a tiny record shop in the Flatiron Arts building. There’s vinyl in the windows, a few crates to flip through, and the whole indie-record-store aesthetic. But head toward the back, past the “Listening Booth,” and you’ll find yourself in one of Wicker Park’s best hidden cocktail bars.
What makes Dorian’s special is the music. They have an Italian-made hi-fi sound system and a proper stage that’s hosted performances from serious jazz, funk, and soul artists. On vinyl DJ nights, the sound quality is incredible — this is a place designed for listening, not just background noise. The cocktail menu is tight and creative (the “DayTime TV” with bison grass vodka and hibiscus water is a standout), and the atmosphere walks that perfect line between sophisticated and laid-back. No pretension, just good drinks and great sound.
6. Nine Bar
Nine Bar was Chinatown’s first craft cocktail bar, and it still might be the coolest. It’s hidden behind Moon Palace Express — one of the neighborhood’s oldest and most beloved takeout spots. Walk through the restaurant to the back and you’ll find this moody, neon-lit space that feels like something out of Blade Runner.
The cocktails here lean into Asian-inspired flavors in the most delicious way. Try the Paradise Lost — cachaça, mango brandy, ube, pineapple, and Thai coconut milk, all clarified to crystal-clear perfection. The bar bites are fantastic too (the spicy dumplings are a must). Owners Lily Wang and Joe Briglio have created something really special here — it’s intimate, the bartenders are genuinely passionate, and you’ll feel like you’ve found a secret that most people don’t know about.
7. The Gatsby
This is the closest you’ll get to a true “solve-the-puzzle” speakeasy experience in Chicago. The Gatsby is hidden on the second floor of Bourgeois Pig, a cozy Lincoln Park cafe. When you check in at the front desk, they hand you a piece of paper with a riddle to solve. You head upstairs, find a room with a bookcase, figure out the riddle, and when you do — a little light goes off inside the bar and they let you in.
Inside, it’s gorgeous. A 1920s theme done right — not the dark, drab version some speakeasies go for, but warm and inviting with a big wooden bar, interesting artwork, and cozy rooms wrapping around the space including a library room in the back. The cocktails are bespoke, the jazz and electro swing music sets the mood perfectly, and there’s a fireplace. If you’re planning a date night in Chicago, this one is hard to beat.
💡 Pro Tip: I won’t spoil the riddle, but I will say this — it’s clever but not impossibly hard. Book your reservation in advance, as there are limited seatings each night.
8. Bordel
Bordel just celebrated its 10th anniversary, and honestly, it keeps getting better. This Parisian-inspired cocktail bar and cabaret is located above Mama Delia (a fantastic Spanish restaurant — so you can do dinner downstairs and drinks upstairs for a perfect evening). Find the unmarked door to the right of the restaurant entrance, head up the stairs, and enter a world of burlesque, live jazz, and craft cocktails.
What makes Bordel stand out is the entertainment. On Thursday, Friday, and Saturday nights, you’ll see world-class burlesque and cabaret performances curated by the amazing Shimmy LaRoux. The staff is enthusiastic and engaging, the cocktails are creative and beautifully presented, and the whole vibe is sexy, theatrical, and undeniably fun. It feels like you’ve stepped into a Parisian cabaret from another era — in the best possible way.
9. Three Dots and a Dash
If you’re looking for something completely different from the dark-and-moody vibe, Three Dots and a Dash is your spot. This hidden tiki bar is tucked down an alley in River North — look for the small sign and follow the path to what feels like a tropical underground paradise. The name comes from Morse code for the letter “V” — as in “Victory” — a nod to the WWII-era tiki bars that inspired the concept.
The cocktails here are spectacular. We’re talking exotic fruits, fresh spices, house-made spirits, and presentations that include flaming garnishes, fresh flowers, and glasses you’ve never seen before. The group drinks — tropical cauldrons loaded with passionfruit, guava, and pomegranate — are the stars of the show and perfect if you’re out with friends. Don’t miss the Bamboo Room, a speakeasy-within-a-speakeasy that seats about 22 and specializes in rare, high-end rum cocktails. It’s a calmer, more intimate spot where you can start your evening before things get lively upstairs.
10. Golden Teardrops
Start with tacos and truck stop nachos upstairs at Lonesome Rose (one of Logan Square’s best Tex-Mex spots), then head downstairs to find this dark, intimate basement bar. A neon sign reading “Weddings & Funerals” glows behind the mahogany bar, which honestly sets the tone perfectly — this is a place for all of life’s moments, big and small.
The cocktails are spirit-forward and beautifully made — mostly creative riffs on classics. There aren’t many seats, so grab one quickly and settle in. Golden Teardrops has that rare quality where you walk in planning to stay for one drink and end up closing the place down. The combination of great cocktails, the intimate space, and the fact that you just ate incredible tacos upstairs makes for a near-perfect night out.
11. Club X
This is one of Chicago’s newest speakeasies, and it opened on December 5, 2024 — the exact anniversary of Prohibition’s repeal. That’s not a coincidence. The space it occupies used to be Club 226, an actual 1920s restaurant with a speakeasy and brothel operating upstairs. The building has real history, and the new owners (second-generation operators of the adjacent Exchequer pub) have leaned all the way into it.
Walk through the unmarked front door, push past floor-length red velvet curtains, and you’re in a retro-mod space that feels fresh and exciting. The cocktails are inventive — beverage director Robertas Plynius does some playful molecular mixology that’s more fun than fussy. The Bee’s Knees (a Prohibition-era classic with lemon, honey, and gin) literally buzzes on your lips. They also pour natural wines and unique liqueurs, which makes it feel more like a neighborhood hangout than a scene. This is a great option if you’re exploring the Loop’s hidden gems.
12. Osito’s Tap
Osito’s Tap is the kind of place that makes you feel like you’ve been let in on a neighborhood secret. It’s hidden inside Moreno’s Liquors, which has been stocking Little Village with hard-to-find tequila and mezcal for over 40 years. Walk to the back of the store, look for the neon Chihuahua sign, and you’ll find a tucked-away bar that once housed a Bohemian drinking spot (a nod to the neighborhood’s old Czech heritage) and an underground bookie joint.
Today it’s one of the most acclaimed bars in Chicago — seriously, it regularly shows up on “best bars” lists — but it’s kept that unpretentious, neighborhood-joint energy. The agave cocktail program is outstanding (this is tequila and mezcal country), the micheladas are legit, and the food menu is inspired by Little Village’s Latinx community. There’s also a not-so-secret patio out back that’s perfect when the weather cooperates. If you want to experience Chicago beyond the typical tourist neighborhoods, this is where to go.
💡 Pro Tip: Pair your visit with a walk through Little Village — Pilsen is right next door, and you can easily make a day of exploring both neighborhoods.
13. Rose Lounge
Take the golden elevator at Adalina (a gorgeous Italian restaurant in the Gold Coast) and descend to Rose Lounge. It’s one of the more glamorous speakeasies in Chicago — think horseshoe-shaped central bar, plush velvet couches, chandeliers, and floral artwork everywhere. The bar has an extensive Champagne and sparkling wine selection alongside complex cocktails like the Walnut Old Fashioned (walnut liqueur, hazelnut, and chocolate-walnut bitters).
Rose Lounge is a great choice when you want to feel fancy without being stuffy. The reservations keep the crowd manageable so it never gets too loud for conversation, and the candlelit atmosphere is romantic without trying too hard. Combine it with dinner at Adalina upstairs and you’ve got yourself one seriously impressive evening.
14. Room 13
This one comes with a caveat: Room 13 is one of Chicago’s most exclusive speakeasies, primarily open to guests of the Old Chicago Inn and its members. But if you can get in (befriend someone who’s in the know, or simply book a night at the inn), you’re in for a treat. The cocktails are crafted from Jazz Age-era recipes, the dress code is cocktail or business casual (they’re serious about it), and the whole experience feels like stepping back in time.
Hotel guests can experience Room 13’s cocktail flight — a tasting of four drinks paired with historical commentary from your bartender. It’s part cocktail bar, part history lesson, and it’s genuinely fascinating. If you’re the kind of person who loves both a great drink and a great story, make it happen.
15. The Library at Gilt Bar
The Library is where you go when you want to feel like you’re at a place where nobody knows your name — and that’s exactly the point. Located in the basement below Gilt Bar in River North, this dark, book-themed space serves classic cocktails and hearty bites from the restaurant upstairs. The energy is mellow, the drinks are strong, and the whole room feels like a private club that somehow lets you in.
The trick with The Library is getting a reservation. Weekend slots are released on Wednesdays, and they go fast. Your other option is to try for one of the limited walk-in spots, which is easier to pull off on a weeknight. Either way, it’s worth the effort — especially if you’re already exploring River North and want somewhere that feels worlds away from the packed bars on the street above.
More Hidden Bars Worth Knowing About
Chicago’s speakeasy scene is always evolving, and these spots didn’t quite make the top 15 but are absolutely worth a visit:
Dorothy Downstairs (Ukrainian Village) — A cozy LGBTQ+ cocktail den with vintage ’70s decor, a rotating cocktail menu, and regular events like “Fruit Salad,” a monthly queer open mic night. Super welcoming vibe.
Nightshade (Portage Park) — Hidden beneath Moonflower, this subterranean grotto serves creative cocktails and shaved-ice drinks on Friday and Saturday nights only. Worth the trip to the neighborhood.
Lulu’s Chambre Privée (River North) — Beneath New Orleans-inspired Storyville, this boudoir-style basement bar features burlesque, magic, live music, and cocktails made with mezcal and activated charcoal. Gilded mirrors, tasseled lamps, the whole vibe.
Sparrow (Gold Coast) — An Art Deco gem tucked inside an apartment building that’s been serving cocktails since 1927. One of the few original-era speakeasies still standing.
Punch House (Pilsen) — A basement bar beneath Thalia Hall with a cozy vibe, DJ sets, and creative punch cocktails.
Tips for Visiting Chicago Speakeasies
After visiting all of these (some of them many, many times), here’s what I’ve learned:
Make reservations whenever possible. These are small spaces. The Alderman has 16 seats. Booze Box fills up by 7pm on Fridays. The Library’s weekend reservations drop on Wednesdays and vanish. Don’t wing it on a Saturday night and expect to waltz in.
Dress smart casual. You don’t need a suit, but leave the gym shorts at home. Room 13 is the strictest (cocktail or business casual required), but even the more relaxed spots have a “date night” energy that you’ll want to match.
Go on a weeknight if you can. Wednesday and Thursday are ideal — shorter wait times, easier reservations, and the bartenders have more time to chat and customize drinks for you.
Budget $40–$60 per person for two cocktails and a small bite. Speakeasy drinks typically run $16–$22 each, and they’re worth it — these are handcrafted cocktails, not well drinks. The exception is Chicago Magic Lounge, where your ticket ($45–$65) includes your first drink.
Pair with dinner nearby. Several of these bars are attached to excellent restaurants: The Alderman to Pilsen Yards, Golden Teardrops to Lonesome Rose, Booze Box to Sushi Dokku, Rose Lounge to Adalina, and Bordel to Mama Delia. Dinner + speakeasy = a perfect Chicago night.
Recently Closed Chicago Speakeasies
Chicago’s bar scene moves fast. A few beloved speakeasies have recently closed their doors, so I want to save you the trip:
The Violet Hour (Wicker Park) — Closed permanently in June 2025 after 18 years due to a landlord dispute. A true Chicago institution that won a James Beard Award and helped launch the craft cocktail movement in the city. Its owners have hinted the brand may resurface somewhere new.
Milk Room (The Loop) — This legendary 8-seat microbar at the Chicago Athletic Association closed in early 2025. It’s been replaced by Midōsuji, an omakase restaurant from the Boka Restaurant Group.
Pigtail (River North) — Chef José Andrés’ pig-themed cocktail bar beneath Jaleo closed in January 2025 when Jaleo shuttered.
Soif Wine Lounge (Logan Square) — This Parisian-inspired wine bar closed in April 2024.
