The 10 best speakeasies in Chicago

Chicago bars that make you hunt for the door come in two kinds: rooms that actually poured during Prohibition, and newer bars built behind alleys, shops and basement shelves. This list ranks the 10 best inside Chicago city limits, for locals planning a night out and visitors who want more than a hotel bar. Each entry spells out how to get in.

The ranking favors bars with documented history and bars where the entrance takes some effort, from an alley off Clark Street to a basement door that needs a key. Costs swing widely. Late-night anniversary sets at the Green Mill carry a $5 cover, house cocktails at Bordel run $16, and the tasting menu at The Office is $198 per person.

How we chose

Bars with a documented Prohibition past rank first, ordered by how well that history is recorded. Next come bars with dated awards or outside recognition. The rest are ordered by how much the entrance asks of a guest, from a key and a booking down to a single concealed door, and the newest room sits last. Every bar was checked against a 2025 or 2026 source, most often the bar’s own site. Three entries also appear in the guide to Chicago cocktail bars, which covers the city’s drink programs more broadly.

Hours and prices below come from each business and change without notice. Call ahead if you are making a special trip.

Green Mill

Few Chicago rooms hold as much Prohibition lore as the Green Mill at Broadway and Lawrence in Uptown. The spot began as Pop Morse’s Roadhouse in 1907, and Capone henchman Jack McGurn was allegedly a part owner during the speakeasy years, according to a 2016 story from the National Trust for Historic Preservation. Dave Jemilo bought the club in 1986 and brought back regular jazz. That well-documented Prohibition story puts the club first. To see the room at full tilt, stay past 1 a.m. on a Friday or Saturday, when the 40th-anniversary late sets start.

Hours: Check current hours before you go.

Address: 4802 N Broadway, Chicago, IL 60640

Why they made the list

• Guests can still sit in the booth that Al Capone and his gang allegedly favored, the National Trust reported.
• The club dates the current Green Mill to June 19, 1986, and marked 40 years in 2026.
• The Friday late show is the Green Mill Jam Session with Marquis Hill, from 1 to 3:30 a.m., with a $5 cover.
• Early sets start at 5 p.m., with Andy Brown on Thursdays and Chris Foreman on Fridays.

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Simon’s Tavern

During Prohibition, Swedish immigrant Simon Lundberg ran a grocery called the Berwyn Food Shop, and local bootleggers asked him to sell whiskey with his coffee. He earned enough to buy the building by 1926 and opened a basement speakeasy, the N.N. Club, short for No Name Club, WTTW reported in 2024. After repeal, the grocery became Simon’s Tavern. That recorded history ranks the Andersonville bar second. These days the way in is the front door at 5210 N Clark St. In cold months, order the glögg, which owner Scott Martin brews 15 gallons at a time.

Hours: Check current hours before you go.

Address: 5210 N Clark St, Chicago, IL 60640

Why they made the list

• Simon’s became a legally licensed bar in May 1934, according to WTTW.
• Scott Martin bought the bar from Roy Lundberg, the founder’s son, and has run the place since 1994.
• The Infatuation describes the holiday glögg as hot mulled wine served with a spice cookie, with a slushie version in summer.

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The Drifter

Enter the main door of the Green Door Tavern in River North and go down the stairs: those are the directions The Drifter posts for lost guests. In the basement, near the bathrooms, one of the knickknacks on the shelves is a doorknob that opens the bar, The Infatuation reports. Green Door Tavern says the room is the only remaining speakeasy room from Prohibition, a claim from the tavern that ranks this bar third. More than 100 rotating cocktails come printed on tarot cards, and burlesque acts take a small stage during the night. Saturday hours run to 3 a.m.

Hours: Wed-Fri 5 p.m. to 2 a.m.; Sat 5 p.m. to 3 a.m.

Address: 678 N Orleans St, Chicago, IL 60654

Why they made the list

• James McCole put up the two-story, balloon-frame building in 1872, right after the Great Chicago Fire, according to Green Door Tavern.
• Green Door Tavern traces tavern service upstairs to 1921 and calls the place Chicago’s oldest tavern.
• When the stage curtains close, they double as a screen for vintage burlesque films, The Infatuation notes.

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Three Dots and a Dash

The address for Three Dots and a Dash reads 435 N Clark St “in the alley,” and the operator describes a secret alleyway entrance that leads underground to a room filled with Polynesian artifacts. Rum drinks come in themed mugs, with island-style plates such as coconut shrimp and pork skewers, per The Infatuation. The same space holds the Bamboo Room, a smaller rum bar that Esquire named one of the best bars in America and North America’s 50 Best listed as One To Watch, according to the bar. That outside recognition ranks the River North tiki bar fourth. Book a weekend table on OpenTable.

Hours: Sun-Wed 4 p.m. to midnight; Thu-Fri 4 p.m. to 1 a.m.; Sat 2 p.m. to 1 a.m. (Bamboo Room: Wed-Sat 4 p.m. to midnight; Sun 4 to 11 p.m.)

Address: 435 N Clark St, Chicago, IL 60654

Why they made the list

• The Bamboo Room keeps shorter hours than the main bar and closes Mondays and Tuesdays.
• Every check carries a 3.5% surcharge, which staff will take off on request.
• Guests must be 21 or older, so bring ID.

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The Alderman

Pilsen Yards, the restaurant and bar on West 18th Street, hides a 16-seat cocktail room that The Alderman describes as sitting behind “a very cool wall.” The room has a four-seat counter and a velvet banquette, and the cocktail list riffs on American classics with seasonal changes. The bar lists a 2022 Jean Banchet Award for Best Bar, a dated honor that places the Pilsen room fifth. Start with the Sichuan Panda, made with baijiu, sesame oil and peppercorn. With so few seats, The Infatuation recommends a reservation.

Hours: Wed-Thu 4:30 to 10 p.m.; Fri 4 to 11 p.m.; Sat 3 to 11 p.m.; Sun 3 to 9 p.m.

Address: 1163 W 18th St, Chicago, IL 60608

Why they made the list

• A neon sign marks the entrance once guests are inside Pilsen Yards, The Infatuation wrote in 2022.
• The Blind Luck mixes gin with chai vermouth, according to The Infatuation’s 2026 speakeasy guide.
• Pilsen Yards runs vinyl DJ sets Thursday through Sunday and closes Mondays and Tuesdays.

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The Office

Below The Aviary on Fulton Market, The Office is a speakeasy in the strict sense: guests need a key to get in, The Infatuation reports, and seats are booked through Tock. The Aviary describes the room as an intimate speakeasy pouring classically inspired cocktails and vintage spirits, and The Infatuation puts cocktail prices at $25 and up. A door that requires both a key and a booking puts The Office sixth, at the top of the bars ranked by entrance. For a shorter visit before dinner, the Office Hour is an hour-long booking that starts at $96 per person.

Hours: Check current hours before you go.

Address: 955 W Fulton Market, Chicago, IL 60607

Why they made the list

• The Office Tasting Menu is prepaid at $198 per person for parties of one to four.
• A standard Office Reservation holds a table for up to 10 guests with a $50-per-person deposit toward drinks and bites.
• For a splurge, The Infatuation points to a $400 Brooklyn made with vintage 1940s whiskey.
• Valet parking is available, according to the Tock booking page.

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Nine Bar

Chinatown’s entry starts at a kitchen door. Guests pass through the kitchen area of the restaurant storefront at 216 W Cermak Rd into a narrow, dark back room, where Nine Bar mixes drinks such as an Old Fashioned with Chinese five-spice, The Infatuation reports. The food runs to mapo fries and a pork cutlet sandwich with tonkatsu sauce. A kitchen door is the next-hardest entrance on this list, which ranks the bar seventh. Plan around Tuesday, the one night the bar is closed.

Hours: Sun-Mon 5 p.m. to midnight; Wed-Thu 5 p.m. to midnight; Fri-Sat 5 p.m. to 1 a.m.; closed Tue

Address: 216 W Cermak Rd, Chicago, IL 60616

Why they made the list

• Hip-hop on the sound system gives the room a lively feel, according to The Infatuation’s 2022 review.
• The bar’s site lists pop-ups and private events on a separate events page.
• The Cermak-Chinatown Red Line stop is about a block away.

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Dorian’s

From the sidewalk, the storefront at 1939 W North Ave in Wicker Park looks like a record shop. Tell the staff you are looking for Dorian’s and they will let you into the bar at the back, The Infatuation wrote in 2018; the outlet’s 2026 speakeasy guide puts the door at the back of the listening room. The bar books live performances and vinyl DJ sets played through an Italian hi-fi system. Walking through a working shop to reach the bar ranks Dorian’s eighth. Arrive early to get a seat for a performance.

Hours: Check current hours before you go.

Address: 1939 W North Ave, Chicago, IL 60622

Why they made the list

• Happy hour runs 6 to 8 p.m. Wednesday through Sunday, according to the bar’s event page.
• Tuesdays are B.Y.O.V. vinyl nights.
• Time Out Chicago has named Jeff Parker and Makaya McCraven among the performers on the stage.
• The Infatuation recommends the Lonesome Cowboy, a rye cocktail with hints of bell pepper.

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Bordel

Upstairs from a Spanish restaurant on Division Street, Bordel keeps an entrance that The Infatuation describes as concealed, in speakeasy fashion. The bar takes the Pigalle and Montmartre districts of Paris as the theme, and the nightly stage brings jazz musicians, burlesque performers, flamenco artists, magicians and cabaret dancers, with DJs between acts. Time Out Chicago covered Bordel in 2014, and the bar is now marking a 12th anniversary. One concealed door is a smaller hunt than a shop or a kitchen, so Bordel ranks ninth. Plan for Thursday through Saturday, the only nights the doors open.

Hours: Thu-Fri 6 p.m. to 2 a.m.; Sat 6 p.m. to 3 a.m.; closed Sun-Wed

Address: 1721 W Division St, Chicago, IL 60622

Why they made the list

• The Spanish Coffee and the Old Fashioned are $16 each on the house cocktail list.
• A porrón of strawberry daiquiri for the table costs $60.
• Groups of up to 14 can book through OpenTable.
• Time Out Chicago lists the Blue Line’s Division stop and the 9, 56 and 70 buses as transit options.

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Culebra

Logan Square’s entry sits under Lonesome Rose, the Tex-Mex-inspired restaurant at 2101 N California Ave. Culebra is a Caribbean and Puerto Rican-themed bar, and the restaurant’s site gives one hint about getting in: “find the entrance, it’ll all sort out.” The Infatuation reported in May 2026 that people outside ask strangers where the entrance is. Order the highball made with Malta, or the plantain shot. Culebra ranks 10th because the bar had just opened when The Infatuation reviewed the room, the shortest track record here.

Hours: Check current hours before you go.

Address: 2101 N California Ave, Chicago, IL 60647

Why they made the list

• The food menu includes a jibarito and a rice crab cake, per The Infatuation.
• A rum swizzle is also on the drink list.
• Lonesome Rose opened in Logan Square in 2017 and added an Andersonville location in 2023.
• The Infatuation added Culebra to the outlet’s speakeasy guide, last updated August 7, 2026.

See the full directory listing

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