Chicago’s River North neighborhood pulses with the same underground energy that once defined the city during Prohibition. Behind unmarked doors and down narrow alleyways, a network of secret bars continues the legacy of those who dared to keep the drinks flowing when the law said otherwise. These aren’t your average watering holes—they’re carefully crafted experiences that transport you back to an era when a good cocktail required knowing the right people and finding the right door.
Today’s River North speakeasies blend authentic 1920s atmosphere with modern mixology, creating spaces where history meets innovation. Here is a list of 17 secret speakeasies that capture the rebellious spirit and sophisticated charm of Chicago’s most storied drinking tradition.
The Library at Gilt Bar
Located below Gilt Bar in River North, The Library creates the perfect scholarly drinking den. The dark, book-lined space feels like sneaking into a university professor’s private study after hours. This candlelit refuge features shelves of leather-bound volumes and red-velvet booths. Reservations for weekends are released on Wednesdays, though you can try snagging limited walk-in slots.
The atmosphere hits that sweet spot between intimate and intellectual, making every conversation feel more profound than it probably is.
Three Dots and a Dash
This River North speakeasy nails the secretive aspect, with an alley entrance, subterranean location, and low lighting. To enter this tiki paradise, walk down the alley directly next to Firecakes on West Hubbard and look for tiki art painted on the building. The name comes from Morse code for V, as in victory, referencing a drink created to celebrate World War II’s end.
Despite being post-war themed rather than Prohibition-era, this tropical hideaway masters the art of concealment that defines any proper speakeasy.
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The Bamboo Room
At the foot of the stairs in Three Dots and a Dash, swoop right to find the intimate Bamboo Room, a compact 16-seat bar offering its own menu of simple yet refined rum creations. This micro-speakeasy within a speakeasy takes exclusivity to another level. The space feels like discovering a secret compartment inside an already hidden treasure chest.
Unfortunately, you’ll have to first contend with a forbidding Wall of Skulls before finding this gem. It’s the kind of place where every seat feels like the best seat in the house.
The Drifter
In the basement of The Green Door Tavern in River North, look for shelves full of tchotchkes where one knick-knack is actually a door knob revealing the entrance to The Drifter. This authentic 1920s-era speakeasy sits on the same floor where drifters have treaded for over 100 years. With over 100 cocktails presented on tarot cards and nightly performances, this hidden gem attracts both cocktail enthusiasts and history buffs.
The mystique deepens when burlesque curtains double as projection screens for vintage entertainment between acts.
Milk Room
What once was a speakeasy during Prohibition is now a hidden eight-seat microbar with a curated selection of whiskey and other rare vintage spirits at the Chicago Athletic Hotel. The seating is unique—you sit along the micro-bar at a slightly lower level, creating a private, intimate vibe.
There’s a welcome drink of champagne, and the space specializes in vintage spirits and whiskies that will elevate your palate. This isn’t just a bar—it’s a whiskey education disguised as a night out.
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Untitled Supper Club
Untitled Supper Club in River North combines a restaurant, whiskey bar, and live entertainment venue, evoking the spirit of a speakeasy with its Prohibition-inspired decor. The space manages to feel both sophisticated and slightly dangerous, like stepping into a gangster’s private dining room.
Live entertainment adds an authentic touch that reminds you why speakeasies became cultural landmarks beyond just drinking. The whiskey selection rivals any serious collector’s private stash, making each visit feel like a masterclass in American spirits.
The Roar Chicago
Head below The Hampton Social in River North for this speakeasy and music lounge with a swankier vibe than most typical nightclubs. You’ll hear everything from live jazz and acoustic sessions to DJ sets, creating a soundtrack that spans generations. Comfy leather couches and chairs provide perfect spots to take breaks from the action.
If you need refreshment, try The Bathtub—a cute vodka-based cocktail served in a tiny bathtub. The venue strikes that rare balance between classy and playful that keeps things interesting all night.
Booze Box
In the back alley of sushiDokku restaurant, look for a bright red neon sign and don’t be alarmed that the door is between dumpsters. Descend the staircase to find yourself in a secret Japanese oasis offering an incredible selection of sake and Japanese whiskey.
The Booze Box doesn’t have a website—if you try to Google the location, only the restaurant pops up. This deliberate invisibility makes discovering it feel like uncovering a genuine secret rather than following a trendy recommendation.
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Pigtail
The River North speakeasy below Chef José Andrés’ renowned restaurant Jaleo channels the flavors of modern-day Spain, drawing inspiration from Spain’s trendy cocktail scene. Miguel Lancha’s cocktail menu features drinks made from Andrés’ favorite ingredient, jamón ibérico, including the Consomé Cocktail with house-made pork consomé and the Negroni Cristal fat-washed in ibérico ham.
Even the mezcal gets the full treatment, distilled with an entire jamón ibérico leg hanging in the still. This isn’t just Spanish-inspired—it’s a full immersion into Iberian drinking culture.
W Lounge
An old jazz lounge in River North caters to fans of craft beers and artisanal spirits, featuring stone walls, high-backed booths, cushy seats, and carpet for an upscale, modern look. Enter the Pops for Champagne bar and look for a W above the stairs. Each of the 16 house cocktails is served in a different vintage glass.
The attention to glassware might seem like a small detail, but it transforms every drink into a mini ceremony that honors both the cocktail and the drinker.
Bordel
Up leopard-print stairs and behind a hidden door, Wicker Park’s Bordel seeks to revive the intrigue of Paris’s belle époque with plush red seats and nightly entertainment. Inspired by old Paris and Prohibition Chicago, Bordel is Moulin Rouge meets Midwest, featuring red velvet, jazz, cabaret, and magic acts. The large format porróns provide perfect accompaniment to watching scantily-clad fire dancers and burlesque performers.
The Spanish coffee deserves special mention—it’s a theatrical drink that matches the venue’s over-the-top energy.
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Room 13
Perhaps one of Chicago’s most exclusive speakeasies, Room 13 is accessible to members and guests of the Old Chicago Inn, where the bar is housed. You’ll need to make friends with someone in the know and obey the strict dress code before sidling up to the bar for classic cocktails crafted from Jazz Age recipes.
Hotel guests can experience Room 13’s cocktail flight—a tasting of four tipples with historical commentary from the bartender. This level of exclusivity feels both pretentious and genuinely special, depending on your tolerance for velvet ropes.
Lulu White
Named for one of the most successful French Quarter madams, the basement space below New Orleans-inspired restaurant Storyville creates a boudoir vibe with couches, gilded mirrors and tasseled lamps. Order classics like a negroni or sidecar, or try signature drinks such as Be My Druidess, featuring mezcal blended with papaya, lime, and activated charcoal. Burlesque dancers, magic shows, and live music add to the sultry atmosphere.
The New Orleans influence creates a distinctly different flavor from typical Chicago speakeasies, bringing Gulf Coast sensuality to Midwest sensibilities.
The Office
Tucked away beneath the former space of Split-Rail sits this LGBTQ+ cocktail den decked out in vintage furniture and 70s-style decor. You’ll find good vibes all around and a rotating selection of intriguing libations, such as the Cup of Cheer made with baking spice bitters, persimmon and bubbles. Regular events include Fruit Salad, Dorothy’s monthly queer open mic night.
The community aspect sets this spot apart—it’s not just about the drinks, but about creating space for connection and self-expression.
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The Violet Hour
Located in Wicker Park, The Violet Hour is an iconic speakeasy known for its creative cocktails and intimate atmosphere. There’s an art to finding the door to this Wicker Park bar, which is usually camouflaged with street art and marked by a lone lightbulb. Inside, observe the posted rules, including no cell phone usage.
The phone policy isn’t just about atmosphere—it forces genuine conversation and presence that most modern bars can’t achieve.
The Cauldron Vault
Housed inside an old bank in Wicker Park, The Cauldron offers immersive potion-making experiences, but the highlight is the Vault—a speakeasy located inside the bank’s safety deposit vault. Exchange wizard currency for a wand-poured drink from the bank teller.
The magic theme could easily feel gimmicky, but the commitment to the concept creates an experience that’s genuinely enchanting. The vault setting adds authentic gravitas that grounds the whimsical elements in real history.
The Gatsby
Although there’s a sign for The Gatsby on the street, it’s hidden inside the Bourgeois Pig café, where you check in at the front desk and receive a riddle to solve. The entrance requires solving the riddle to figure out how to gain access, featuring the best entrance of any Chicago speakeasy.
Inside, the 1920s theme is perfectly executed with interesting artwork, a big wooden bar, and a series of rooms wrapping around for a cozier feel, plus a library room in the back. The riddle element adds genuine mystery that most ‘secret’ bars have lost in the Instagram age.
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Where History Meets Mystery
The River North speakeasy scene proves that some traditions never go out of style. These hidden gems continue Chicago’s legacy of creative defiance, where the best experiences happen behind unmarked doors and below street level. Each speakeasy reveals a unique facet of Chicago’s Prohibition-era heritage, but they also create new stories for every guest willing to seek them out.
From hidden alleyway entrances to glamorous underground lounges, these establishments offer more than just cocktails—they provide a captivating journey into the city’s storied past. The next time you’re wandering River North’s bustling streets, remember that the most memorable night might be waiting just behind that innocent-looking door you almost walked past.
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