From the bar behind a laundromat to the hidden bookshelf door in a basement, these are the speakeasies locals actually go to.
Chicago has more good speakeasies than any other American city, and that makes sense. This is the city Al Capone built his empire in, where a thousand actual speakeasies operated during Prohibition.
Today’s version is different from the 1920s original, but the feeling is similar. You walk into what looks like a barbershop, a laundromat, or an unmarked alley door. You give a password, knock on a hidden bookshelf, or solve a riddle. The room behind the door is intentionally mysterious. The cocktails are some of the best in the city.
We asked our Facebook regulars for the best speakeasies in Chicago. Here are the 13 that came up, organized by what kind of night you’re planning.
1. The Drifter
📍 676 N Orleans St, Chicago, IL 60654 (River North)
The most genuinely historic speakeasy in Chicago. The Drifter sits in the basement of the Green Door Tavern, the oldest wooden bar building in Chicago, built in 1872 right after the Great Fire. The basement was an actual Prohibition-era speakeasy in the 1920s, on Dean O’Banion’s bootlegging circuit (not Capone’s, despite what some guides claim). The space was used as storage for decades after Prohibition ended, until the current owners discovered the original hidden door behind a credenza during a renovation and reopened the basement as a working speakeasy in 2017.
You enter by walking into the Green Door Tavern, going down the back stairs as if you’re heading to the restrooms, and finding the bookshelf at the bottom. Knock on the bookshelf. The door opens. Inside is a 37-seat space with original 1920s tapestries, a working stage, and a bar that pours classic cocktails alongside the rotating tarot card menu (each drink corresponds to a card from a deck of 100+).
The room runs nightly burlesque performances, magic acts, and live music every 30 to 55 minutes after 6:30pm. There’s typically a $6 cover to support the performers. Open Wednesday through Saturday, 5pm to 2am.
Local tip: Reserve through their website. The space fills up fast, especially on weekends. The burlesque shows are part of the experience, not optional, so know what you’re getting into.
2. The Meadowlark
📍 2812 W Palmer St, Chicago, IL 60647 (Logan Square)
The most acclaimed new cocktail bar in Logan Square, hidden in plain sight on a quiet side street. The Meadowlark shares a 110-year-old building with sister concepts Lardon (a sandwich shop) and Union (a beer-focused restaurant), but the bar has its own separate entrance off the back alley on Palmer Street. Look for the small bird silhouette sign above an unmarked door. Knock on the metal door, the host opens it.
The bar was founded by the team behind Lardon and Union along with beverage director Abe Vucekovich, an alum of the legendary Violet Hour (which closed in June 2025). The cocktail program runs in fully themed menus that rotate every several months. Past menus have included “Birds of the Midwest” (with cocktails inspired by individual bird species, paired with vintage Audubon watercolors and pocket guide booklets you can take home) and “Chicago World’s Fair” (drinks based on the 1893 Columbian Exposition).
The space is 825 square feet, 30 seats total. Exposed brick. Leather Chesterfield couches. Brass library lights. Bookshelves. The whole thing feels more like a private library than a bar.
Local tip: Walk-ins welcome at the bar, but lounge reservations through Resy are smarter on weekends. The themed cocktail menus are worth ordering through entirely. Ask the bartender to recommend three drinks in sequence rather than picking individually.
3. Three Dots And A Dash (And The Bamboo Room)
📍 435 N Clark St, Chicago, IL 60654 (River North)
The most famous tiki speakeasy in the United States. Three Dots and a Dash sits underneath Bub City, the country-music-themed restaurant on Clark Street. To find it, walk down the alley off Hubbard Street. Look for the wall of skulls. Walk through the unmarked door. A staircase descends into a basement done up in full-throated tiki style, with a thatched bar, hand-carved tiki gods, hanging grass, and Polynesian decor everywhere.
The cocktails are some of the best tiki drinks in America. The bar is run by Paul McGee, one of the most respected tiki bartenders working today, and the menu rotates between original creations and recreated classics from the original tiki era. Cocktails are usually served in elaborate vessels: hollowed pineapples, ceramic tiki mugs, smoking volcanoes meant for sharing.
Inside Three Dots, behind another curtain, is the Bamboo Room: a 12 to 14 seat reservation-only inner speakeasy that focuses on rare and vintage rums. Over 200 different rums on the menu. The Bamboo Room runs progressive tasting flights and pairs cocktails with small bites. It’s harder to get into and significantly more upscale than the main bar.
Local tip: Book the Bamboo Room through their website specifically if you want the quieter experience. Three Dots itself is loud and crowded on weekends, which is part of the charm but not for everyone. Don’t try to order off-menu. The bartenders know what they’re doing.
4. The Office (Beneath The Aviary)
📍 955 W Fulton Market, Chicago, IL 60607 (West Loop / Fulton Market)
The hardest speakeasy to get into in Chicago. The Office is a 21-seat (formerly 14-seat) speakeasy hidden behind a locked unmarked door in the basement of The Aviary, the molecular gastronomy cocktail bar from Grant Achatz and Nick Kokonas of the Alinea Group. The bar takes its name from the original architectural blueprints, which labeled the small basement room as “the office.”
For years, The Office operated by invitation only. Repeat Aviary, Alinea, and Next customers were given a private phone number to text reservation requests. Walk-in access from The Aviary upstairs was occasionally possible if a server invited you down, but it was never guaranteed. As of 2026, reservations can be booked through Tock with advance planning, though demand still vastly exceeds supply.
The cocktails are intentionally different from the upstairs experience. Where The Aviary trades in molecular gastronomy and theatrical presentations, The Office serves classically inspired cocktails built around individual spirits. The bar holds an extensive library of vintage and rare spirits, including pre-Prohibition bottles and rare whiskies that can run hundreds of dollars per pour. There’s also a small luxury food menu (foie gras, crab, oysters).
Local tip: Book via Tock weeks in advance. Closed Sundays and Mondays. Cocktails are around $20 each, vintage pours are significantly more. Eat at The Aviary upstairs first if you’re making a full evening of it, and ask the staff if they can extend your reservation downstairs.
5. Chicago Magic Lounge
📍 5050 N Clark St, Chicago, IL 60640 (Andersonville)
The entrance is a working laundromat. You walk in expecting to see washing machines. You push through a hidden door (a fake washing machine front), and you enter a 1930s-style supper club dedicated entirely to close-up magic.
We covered this in detail in our Hidden Gems guide, but it earns a spot on this list too. The Magic Lounge runs three performance spaces. Live magic happens at every table during dinner. A separate cabaret-style theater hosts the main shows. A speakeasy bar serves classic cocktails between performances. Performers range from sleight-of-hand experts to mind readers to internationally touring magicians.
Wednesday through Sunday. Tickets start around $40. Reservations are required and weekend shows often sell out a month in advance. Dress code is enforced.
Local tip: Wednesday “Resident Magician” shows are the most affordable entry point and showcase the regular performers. The 654 Club is the most exclusive private room and worth booking if it’s available. Don’t bring kids. The vibe is unapologetically adult.
6. Blind Barber
📍 948 W Fulton Market, Chicago, IL 60607 (Fulton Market)
By day, a working barbershop. By night, an unmarked back door leads into a 1970s-themed cocktail lounge with plush wood paneling, mood lighting, and a DJ booth. The original Blind Barber concept started in New York in 2010, and the Chicago location opened in 2018, occupying the same Fulton Market footprint as the rest of the neighborhood’s restaurant boom.
The barbershop is real. You can actually book a haircut. The cocktail bar in the back is also real, and locals do treat it as a regular Friday night spot rather than just a novelty. Cocktails are old-fashioned heavy and the music tends toward funk, soul, and classic hip-hop on busy nights.
Local tip: Walk-ins are usually fine on weeknights. Friday and Saturday after 9pm gets crowded. Order anything off the rotating cocktail list and you’ll be fine.
7. Nine Bar
📍 2138 S Archer Ave, Chicago, IL 60616 (Chinatown)
Hidden behind a takeout counter in Chinatown. You enter through what appears to be a food spot, walk past the kitchen, and find yourself in a vaporwave-aesthetic cocktail bar that genuinely doesn’t look like anywhere else in Chicago. Pink and teal neon. Asian-inspired cocktails using ingredients like baijiu (Chinese white liquor), Sichuan peppercorns, ume plum, salted plum, yuzu, and pandan.
The cocktails are precisely engineered and the bartenders treat the bar program like a kitchen. Drinks come with detailed printed cards explaining the ingredients. Many of the spirits used aren’t carried at any other bar in the city.
Local tip: Reserve through their website. The space is small and books up fast on weekends. Order something with baijiu if you’ve never had it. It’s the most distinctive thing on the menu.
8. The Gatsby
📍 2926 N Lincoln Ave, Chicago, IL 60657 (Lincoln Park)
The most theatrical entrance experience in Chicago. The Gatsby is a Lincoln Park speakeasy that requires you to solve a riddle to find the hidden door, then enter a passcode to get in. The riddle and code are sent to your phone after you make a reservation. Show up without doing the work and you’re not getting in.
The bar inside leans hard into 1920s glamour. Velvet booths, art deco lighting, jazz playing at conversation volume, and a cocktail menu themed around F. Scott Fitzgerald and the Jazz Age. The drinks are competent but the entrance experience is the real draw.
Local tip: Read the confirmation email carefully. Some groups arrive without solving the riddle and the staff will hold them at the door. Dress to match the theme. Casual will get you turned around at the threshold.
9. Bordel
📍 1721 W Division St, Chicago, IL 60622 (Wicker Park)
A Wicker Park speakeasy hidden above the tapas restaurant Black Bull. You enter through a curtained doorway and climb a flight of stairs into a space designed to feel like a Parisian bohemian salon. Velvet, candlelight, antiques, and a small stage that hosts live flamenco guitar, burlesque, and cabaret performances throughout the week.
The cocktails are Spanish and French-influenced. Sherry-based drinks. Gin and tonics built like the ones served in San Sebastian. A small absinthe program. The crowd is dressed up. The energy is closer to a private party than a bar.
Local tip: Reserve through their website, especially for performance nights. The flamenco evenings book up two weeks ahead. Dress sharply.
10. Dorian’s
📍 2008 W Division St, Chicago, IL 60622 (Wicker Park)
The entrance is through a record shop. You walk into Dorian’s Through The Record Shop, browse vinyl, push the right door, and find yourself in a candlelit cocktail bar that runs live jazz and soul music nightly. The space is named after Dorian Gray, and the aesthetic leans into that fully: gilded mirrors, dark velvet, antique chandeliers, and the kind of lighting that makes everyone look better than they actually are.
The cocktail program focuses on classic preparations done precisely. The food menu is small but excellent, with raw bar items and a few French-influenced plates. Music starts around 8pm most nights.
Local tip: The record shop section is genuinely worth browsing before you push through. The owners curate the vinyl carefully and you can buy what you find. Tuesday and Wednesday nights have the best music programming and the smallest crowds.
11. Club X
📍 The Loop, exact address available on reservation
A retro cocktail bar tucked into the Loop, focused on natural wine and modern classic cocktails. Club X leans into the cozy, moody aesthetic that Chicago does well, with red leather banquettes, low lighting, and a small but thoughtful drink list.
The bar is intentionally low-key. No social media presence to speak of. Limited online information. Reservations are released in narrow windows. It’s the closest thing Chicago has to a true insider’s bar in 2026.
Local tip: Reserve through their site directly. Walk-ins are not really a thing here. The natural wine list is the move if you don’t want to do cocktails.
12. Untitled Supper Club
📍 111 W Kinzie St, Chicago, IL 60654 (River North)
The largest speakeasy on this list, and the most theatrical. Untitled is a multi-room basement supper club that runs across roughly 10,000 square feet underneath Kinzie Street. There’s a main lounge, a “library” with leather chairs and a working fireplace, a dining room, multiple bars, and a stage that hosts live music throughout the week, ranging from jazz to soul to burlesque.
The cocktail program is solid but not the main draw. The vibe is. Untitled feels like a private club rather than a hidden bar, and the energy is consistently high without ever tipping into chaos. It’s where Chicagoans take out-of-town friends when they want to make Chicago look glamorous.
Local tip: Reserve through their website, especially for live music nights. The library room is the most photogenic. The full whiskey program is one of the best in Chicago, with over 400 expressions on the menu.
5 Essential Tips Before Visiting A Chicago Speakeasy
1. Make A Reservation
Most Chicago speakeasies are small, and walk-in availability evaporates after 7pm on any night ending in Y. Reserve through Resy, OpenTable, or directly with the venue. Weekend reservations book up two weeks ahead.
2. Dress For It
Most speakeasies enforce a smart-casual dress code at minimum. No athletic wear. No flip flops. No shorts after 6pm at the upscale ones. When in doubt, dress like you’d dress for a date at a nice restaurant.
3. Read The Entrance Instructions
Half the experience is finding the door. Read the venue’s website before you go. Some entrances are hidden behind retail businesses. Some require a knock. Some require a password sent via confirmation email. Showing up without doing the homework defeats the entire point.
4. Don’t Photograph The Other Guests
Speakeasies are designed for intimacy. Photography of your own table and drinks is fine. Photography of strangers is not. Most venues will ask you to put your phone away if you start filming the room. Respect that.
5. Tip Like You Mean It
Speakeasy bartenders are pouring $18 cocktails that take six minutes to make. They are not pulling pints. Tip 20% minimum. Tip more if the bartender clearly took time on your drink. The good ones remember regulars and good tippers, and you’ll get treated better on your next visit.
The Bottom Line
Chicago’s speakeasy scene is genuinely one of the best in America, and that’s not just marketing. This is the city where a thousand actual speakeasies operated during Prohibition, where Dean O’Banion ran his bootlegging operations, and where the modern American craft cocktail revival has produced bars that compete with anything in New York or San Francisco.
If you only have time for one, do The Drifter. It’s the most historically authentic, the cocktails are excellent, and the entrance experience is the real thing rather than a recreation.
If you want the cocktails-first experience, do The Meadowlark in Logan Square or Three Dots and a Dash in River North.
If you want the most exclusive experience and you’re willing to plan ahead, book The Office or the Milk Room.
If you want pure spectacle, the Chicago Magic Lounge and The Gatsby will both deliver.
Whatever you book, dress for it, reserve ahead, and put your phone away. Speakeasies work because they ask you to slow down. Let them.
