The Coziest Speakeasies in Chicago (and Where to Find Them)

Leah Fishman

Chicago's speakeasy scene is not just about hidden entrances, secret passwords, and creative cocktails. It's also about the vibes and the ambiance. From dimly lit corners to flickering candles, these Chicago speakeasies create the perfect atmosphere to unwind, relax, and enjoy a drink. Whether you're looking for a romantic date spot or a cozy night out with friends, these speakeasies offer a little something for everyone.

Tags: Cozy, Hidden Gems, Speakeasies

  • The Drifter in Chicago, United States

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    • leah

      The Drifter, located in the basement of The Green Door Tavern in River North, is Chicago speakeasy accessed through a secret door disguised as a knick-knack on the shelves of the tavern's bathrooms. Inside, you'll find an atmosphere straight out of the Prohibition era, complete with antiques, an old American flag, and occasional burlesque performances on a small stage.

  • Golden Teardrops in Chicago, United States

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    • leah

      Golden Teardrops, located beneath Lonesome Rose in Logan Square, can be accessed through the restaurant or a discreet alleyway entrance. With a cozy and dimly lit atmosphere, it's perfect for a chill catch-up with friends or letting loose during Wednesday night karaoke. The bar's string lights add ambiance without requiring the use of a smartphone flashlight.

  • Nine Bar in Chicago, United States

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    • leah

      Nine Bar, Chinatown's first speakeasy and cocktail bar, is located behind Moon Palace Express' kitchen door. The bar offers a fun and funky menu of Asian-inspired food and drinks, including unique takes on classic cocktails and must-try snacks like general jones' wings: wok-fried wings tossed in Moon Palace Express' general tso's sauce. With a cozy but spacious atmosphere, Nine Bar is perfect for a lowkey and cozy hangout during weeknights and energized by DJ sets on weekends.

  • The Alderman in Chicago, United States

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    • leah

      Located within the trendy Pilsen Yards, The Alderman is an intimate bar-within-a-bar speakeasy that seats 16 guests. Guests can indulge in classic cocktails created by Lance Bowman, one of Chicago's most highly awarded mixologists, while relaxing on cozy plush velvet banquettes.

  • Bordel | Cabaret & Cocktail Bar in Chicago, United States

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    • leah

      Bordel, located above Mama Delia on Division, is a long-running and secretive speakeasy accessed via an unmarked door atop a red stairwell. With fire eaters and burlesque performers, Bordel aims to transport guests to a sultry Parisian night for an cozy and intriguing experience in Chicago.

  • Room 13 in Chicago, United States

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    • leah

      Room 13, located inside the Old Chicago Inn, is a highly exclusive speakeasy accessible only to members and guests of the Inn. To enjoy classic cocktails crafted from Jazz Age recipes, make sure to befriend someone who knows the secret dress code. Opt for the cocktail flight, which includes four drinks and stories about the building's history from the bartender.

  • Blind Barber in Chicago, United States

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    • leah

      Blind Barber is a late-night spot hidden behind a functioning barber shop. It has a dark, divey atmosphere with wood paneling and a checkered floor. Order a cocktail and smash burger at the bar and enjoy the rotating DJs until the wee hours. To up the speakeasy's cozy vibes, the space features burnt-orange leather sofas, knotty pine walls, and glass block windows nodding to Fulton Market's meatpacking past.

  • Dorian’s in Chicago, United States

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    • leah

      Venture through a small record shop entrance in Wicker Park to unveil Dorian's: a music-centric speakeasy bar in Chicago This sophisticated establishment features a high-end Italian sound system, perfect for vinyl DJ nights, and a full stage with live music.

  • Soif Wine Lounge in Chicago, United States

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    • leah

      Soif, pronounced "swaf" like the French word for thirsty, is an intimate Parisian-style bar located below Testaccio in Logan Square. This romantic hideaway is perfect for wine lovers, offering a rotating wine list of approximately 50 to 60 bottles in its subterranean space.

  • The Office in Chicago, United States

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    • leah

      The Office is a tiny speakeasy located beneath the acclaimed cocktail bar, The Aviary, in the West Loop of Chicago. To have a super memorable experience, reserve one of the four bar stools during their Office Hour, a 60-minute guided session where guests can enjoy two personalized cocktails paired with food — perfect for before or after dinner drinks!

  • The Violet Hour in Chicago, United States

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    • leah

      Violet Hour is a bar with no signs, housed in a building with an ever-changing mural, and a long line of patrons waiting outside. Inside, the seating areas are private and cozy, and the bartenders are some of the most talented in the city, serving both classic and seasonal cocktails. The bar has house rules, that includes "no cell phones, no light beer, no O-bombs, no Jager-bombs, no bombs of any kind..."

  • Three Dots and a Dash in Chicago, United States

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    • leah

      Three Dots and a Dash is a tropical-themed bar located in Chicago's River North area, led by cocktail expert Kevin Beary. They specialize in crafting cocktails using fresh exotic fruits and spices, premium rums, and house-made juices and elixirs. Inside the bar, the Bamboo Room offers a guided tour of the world of rum.

  • Pigtail in Chicago, United States

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    • leah

      Pigtail is a basement bar located below Jaleo on 500 N. Clark Street, offering an intimate speakeasy-style experience with a Spanish influence. Created by world-renowned chef José Andrés, it is known for serving braised pig’s ears, and Jamón Ibérico-infused cocktails.

  • Moonflower in Chicago, United States

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    • leah

      Nightshade is a basement bar located beneath Moonflower in Portage Park. It features a cozy atmosphere with couches, tea candles, and strong drinks, and has a unique menu that includes shaved ice drinks like the Espresso Martini and original creations like the Son of a Gun. It's open on Thursdays, Fridays, and Saturdays.

  • Dorothy in Chicago, United States

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    • leah

      Dorothy is an underground lesbian cocktail lounge located in Chicago's West Town area, featuring a 70s-inspired decor and a welcoming environment for all friends of Dorothy. With exceptional event programming and creative cocktail offerings, it is the perfect cozy space to express yourself. Look for the entrance in the basement of Split-Rail.

  • The Blue Room in Chicago, United States

    • leah

      Located beneath the Chicago Firehouse Restaurant in the South Loop, the city's newest speakeasy is a basement bar with a cozy and romantic ambiance, complete with vintage decor, leather booths, and an Art Deco aesthetic. The whiskey-focused drink menu features smoked cocktails that align with the venue's former fire station identity.

  • The Milk Room in Chicago, United States

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    • leah

      Milk Room, a microbar with only eight seats, has a fascinating history as a former speakeasy in Chicago during Prohibition. It offers a specialized cocktail menu that focuses on the flavor of spirits, crafted exclusively from rare vintage spirits and elixirs, and an extensive collection of carefully curated whiskies.

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