The best Chicago speakeasy bars to discover

The Green Door Tavern used to be patronized by Chicago gangsters, taking its name from the discreet entrance on the side of the building. If you walk down the metal staircase leading to the bathroom, you’ll notice a knickknack-covered door to a room that housed a speakeasy in the ’20s. Today it's the entrance to the Drifter, a craft cocktail bar with live entertainment and funky decor. Guests are invited to order from a stack of custom-made tarot cards that act as a constantly rotating menu. Sit back, sip your drink and take in old-school entertainers like contortionists and belly dancers.

Many of the watering holes on this list are intimate, but the Chicago Athletic Association's Milk Room is a true micro-bar, with just eight seats available to guests. Though the cocktails here cost a pretty penny (upwards of $40–$50 a pop), they're crafted with rare vintage spirits like 1970s Cointreau, 1960s rum and 1950s Fernet Branca. After you're done with the boozy history lesson, get some fresh air and take in the views upstairs at rooftop lounge Cindy's.

You won't see any signs for Violet Hour, only a long line of people waiting outside of an ever-changing, abstractly painted building. Once inside, the first thing you'll spot is a list of "house rules," which limits cell phone use (take your calls outside the bar) and outline contraband (domestic beer, White Claw, top shelf vodka and late ‘90s club cocktails). Seating areas are designed to be cozy and private so that guests don't have to shout over ambient noise. Plus, the crew behind the bar comprises some of the city’s most talented bartenders, who mix classics and seasonal concoctions.

Moreno's Liquors has stocked Little Village with shelves upon shelves of tough-to-find tequila and mezcal for more than 40 years. Head to the back of the store, though, and you'll find a neon Chihuahua sign guiding you to Osito's Tap, a tucked-away space that once housed a Bohemian bar (true to the neighborhood's old Czech heritage) and an underground bookie joint. Nowadays, the bar serves a drink and food menu inspired by Little Village's Latinx community, with an especially strong showing of agave cocktails and michelada options, plus a hefty selection of draft beer. Cozy up in high-backed leather booths indoors or venture outside to the not-so-secret patio for a drink in the sunshine.

You won't soon forget an evening at the Office, a tiny speakeasy hidden below lauded cocktail bar the Aviary in the West Loop. Your best bet is to reserve one of four bar stools for the Office Hour, a 60-minute guided experience that includes two bespoke cocktails and snack pairings (ideal for pre- or post-dinner tipples). Can’t decide on a drink? Opt for the Dealer’s Choice and let the expert bartenders craft a concoction tailored to your preferences.

Tucked away beneath the former space of Split-Rail sits this LGBTQ+ cocktail den that’s 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. There are also regular events and programming like Fruit Salad, Dorothy’s monthly queer open mic night.

Located in the basement of Tex-Mex restaurant Lonesome Rose, this dark and intimate establishment welcomes guests in for a cozy nightcap after a round of tacos and truck stop nachos. Belly up to the mahogany bar, which is illuminated by a neon sign that reads “Weddings & Funerals,” order a drink—mostly spirit-forward riffs on classic cocktails—and then try to grab one of the few available seats. It’s an inviting hideout that beckons you to stay a while.

Venture through a petite record shop storefront in Wicker Park to discover Dorian’s, a cocktail bar built around music (or behind music, if you want to get literal). The elegant space boasts an Italian-made hi-fi sound system for vinyl DJ nights and a stage for live music—where the bar has hosted performances from luminaries like Jeff Parker and Makaya McCraven—plus a narrow menu of house cocktails perfect for sipping while you listen. 

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. Make friends with someone who's in the know and obey the strict dress code (cocktail or business casual) before sidling up to the bar for classic cocktails that are crafted from recipes that date back to the Jazz Age. Hotel guests can opt to experience Room 13's cocktail flight, a tasting of four tipples along with historical commentary from your bartender.

Ever feel like going somewhere where no one knows your name? That's the vibe at the Library, which is located below Gilt Bar in River North. The dark, library-themed bar slings classic cocktails and hearty bites from upstairs. Reservations for each weekend are released on Wednesdays, though you can also try your hand a snagging one of the bar’s limited walk-in slots. 

Hidden away on the second floor of Lincoln Park’s Bourgeois Pig, this intimate cocktail den is filled with bookshelves, 19th and 20th century oil paintings, chandeliers and a fireplace. To gain access, you’ll first have to solve a riddle to find the secret entrance and then recite a password. Once inside, indulge in bespoke concoctions and light bites while being serenaded by jazz, electro swing and crooner tunes. If you’re looking for a romantic date night destination, this is it.

On Friday and Saturday nights, visitors to Moonflower in Portage Park can saunter down to the bar’s subterranean space to discover Nightshade, a speakeasy-style grotto serving a sophisticated selection of cocktails. Choose from creative sippers like the Late Bloomer (purple rice-washed Ford’s Gin, coconut, cinnamon, lime) and Sneaking Suspicion (chamomile, cinnamon, lemon, clarified yogurt, rum, vodka and “fancy ice”) or go all-out and order from a menu of fanciful cocktails made with fluffy mounds of shaved ice.

Try googling “The Alderman Chicago” and you’ll be lost in a sea of city websites—and maybe that’s intentional. The 16-seat speakeasy-style bar, tucked away in an tiny, candlelit side room of Pilsen Yards, offers an intimate hideaway for sipping through beverage director Lance Bowman’s sophisticated cocktail menu, plus a long list of spirit pours. Overwhemed by the thick menu and dim lighting? Staff are eager to help indecisive visitors sort through the not-insignificant cocktail list. A word to the wise: Don’t show up without a reservation, especially on the weekends.

Take the golden elevator at Adalina down to Rose Lounge, where you can grab a seat at the horseshoe-shaped central bar or the plush velvet couches around the perimeter. Lit by candles and chandeliers and decorated by floral art to go with the name, the bar offers an extensive selection of Champagne and spirits plus complex cocktails. You’ll also find premium spins on classics like the Walnut Old Fashioned made with walnut liqueur, hazelnut and chocolate-walnut bitters. Reservations are required for most of the night to ensure it doesn’t get too crowded for intimate conversations.

Chinatown’s first cocktail bar doubles as one of the city’s coolest speakeasies. Located in the former dining room of longtime neighborhood restaurant Moon Palace (now offering takeout as Moon Palace Express), Nine Bar is a moody, Blade Runner-esque space—think neon lighting, sleek furniture and touches of industrial decor—with a killer menu of cocktails and bar bites that owners Lily Wang and Joe Briglio have dubbed “Asian-ish.” We’re especially fond of Paradise Lost, a buttery-smooth concoction made with cachaçha (a fermented sugarcane spirit from Brazil), Rhine Hall mango brandy, ube, pineapple and Thai coconut milk, then clarified to crystal-clear perfection.

The folks behind Three Dots and a Dash surprised us with a bar-within-a-bar concept called the Bamboo Room, where guests can sip cocktails mixed with rare and high-end rums. The 22-seat area offers a menu curated by beverage director Kevin Beary; expect simple, well-balanced beverages that are more refined than their Three Dots counterparts. In the mood for something bespoke? Order a Dealer's Choice and your bartender will create a custom, off-menu rum cocktail based on your imbibing preferences. 

Named for Lulu White, one 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. Settle in and order a classic cocktail like a negroni or sidecar or a signature sipper such as Be My Druidess, mezcal blended with papaya, lime and activated charcoal. Burlesque dancers, magic shows and live music add to the sexy fun.

Up leopard-print stairs and behind a hidden door, Wicker Park’s Bordel is a speakeasy that seeks to revive the intrigue of Paris’s belle époque. Order one of the classics, like the Spanish coffee, and settle into the plush red seats as you take in the bar’s nightly entertainment. The large format porróns are the perfect accompaniment to watching the scantily-clad fire dancers and burlesque performers that frequent the stage at this lively bar late into the evening.

True to form, Brando’s Speakeasy is not what it seems. It’s a lounge, yet conversation flows more like a neighborhood haunt. The cocktail menu features interesting drinks, like the root beer old fashioned. The decor and vintage posters throw it back to yesteryear, but the karaoke and late-night dance music add modern flair.

Hidden behind a fully functioning barber shop, this raucous late-night spot is dark and outfitted with wood paneling, a checkered floor and divey lounge furniture. It's where the beard trims end and the imbibing begins. Grab a seat at the bar and order a cocktail and a grilled cheese. A rotating cast of DJs keeps the dance floor packed into the wee hours of the morning.

Concealed in the depths of Thalia Hall, this dark, ’70s-themed bar is decorated with a fish tank, wood paneling and a huge fish on the wall. Think of it as an upgraded, boozy version of your grandparents' basement. Like its name suggests, punch is the main draw here—and you can order most cocktails by the glass, carafe or bowl. Whether you go big or small, you'll experience the genius and precision happening behind the bar at Punch House. If you're looking for a good place to start, order Space Juice for Jered, a blend of tequila, grapefruit, lime, black pepper, sparkling wine and sage.

The menu at this underground speakeasy—located beneath celebrity chef José Andrés' flagship restaurant, Jaleo—centers around one ingredient: Jamón ibérico, the dry-cured Spanish ham that's prized for its smooth, nutty taste. You'll find the jamón nestled into dishes like a "taco" with caviar, quail egg and ibérico de bellota as well as on the drink menu, which includes savory beverages like the Consomé Cocktail, a combination of a house-made pork consomé with palo cortado and amontillado sherries topped with egg foam. 

Styled after the intimate bars of Paris, Soif—pronounced "swaf," like the French word for thirsty—is a romantic hideaway for wine lovers, with a rotating wine list of around 50 to 60 bottles served in a subterranean space below Testaccio in Logan Square. Sidle up to one of the bar's plush velvet banquettes to peruse a menu that highlights small batch and limited production wines (like grower Champagne, which is produced in small volumes by the same person who grew the grapes) as well as natural and orange wines.

From the outside, you wouldn’t guess that Sushi Dokku in West Loop has something to hide, but insiders know about the subterranean bar with izakaya-style small plates that waits below. Once you know what you’re looking for, you’ll feel like a covert spy on a mission for boozy cocktails and quality hip-hop music. Head to the alley just behind Sushi Dokku (not sketchy at all) and look for the red light above a door—you've successfully found Booze Box. Psst! If you can’t find it, the staff will be happy to escort you downstairs.

Have you ever wanted to be a witch or wizard? Well, make your dreams come true at this magic-themed concept in Wicker Park. Housed inside an old bank, The Cauldron is a full-service restaurant and bar offering immersive potion-making experiences—cocktail classes–plus British comfort fare and a creative selection of concoctions. The highlight of the space, though, is the Vault: a speakeasy located inside the bank’s safety deposit vault. There, you can exchange wizard currency for a wand-poured drink from the bank teller.

Head below The Hampton Social in River North for this speakeasy and music lounge with a swankier vibe than most typical nightclubs. Expect to hear everything from live jazz and acoustic sessions to DJ sets, plus there are comfy leather couches and chairs for when you want to take a break. If you need a refreshment, try The Bathtub—a cutesy vodka-based cocktail served in a tiny bathtub.

In addition to its library and museum, both packed with historical acquisitions, the Irish American Heritage Center boasts a cozy limited-hours pub with free live music (Irish, of course) and Guinness-absorbing classics like fish and chips. If everyone were as beer-minded as the Irish, cultural institutions would be flooded with the thirsty and eager to learn.