11 secret speakeasy bars to discover in Chicago

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, porto. After you're done with the boozy history lesson, get some fresh air and take in the views upstairs at rooftop lounge Cindy's.

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.

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 several bespoke cocktails and food pairings (ideal for pre- or post-dinner tipples). Booze aficionados can spring for the Dusty Bottle Experience, with three vintage classic cocktails that are mixed using spirits from 1960 to 1980—a blast from the past in liquid form.

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.

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 sandwich served on artisan country white bread. A rotating cast of DJs keeps the dance floor packed into the wee hours of the morning.

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.

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.

Located below Dusek’s Board & Beer, 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, Luxardo bitters, black pepper, sparkling wine and sage.

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. Staff are eager to help indecisive visitors sort through the not-insignificant cocktail list, but we're particularly fond of the bar's tea-based concotions; Becky on the Beach pairs toasty genmaicha with rum, bitters and lime for an earthy-yet-tropical sipper. A word to the wise: Don’t show up without a reservation, especially on the weekends.