Chicago speakeasy bars
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 Fernet Branca, 1980s Campari and 1960s Benedictine. 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 laundry list of "house rules," which prohibit cell phone use, enforce the dress code (no baseball hats) and outline contraband (Jager bombs, light beer, Grey Goose and Cosmopolitans). 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.
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 nerds 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.
The aptly named Ladies' Room can be accessed through a curtain near the bathroom at Fat Rice in Logan Square. The space is so small that you might just miss it—which would be a huge mistake. The talented team behind the bar mixes elixirs with house-made infusions and syrups, rare spirits and funky flavors. Expect to see eyebrow-raising ingredients on the menu, like avocado leaf tincture, salted coconut foam, sherry butter and smoked maple syrup. Because seating is limited and insiders love this place, you typically need a reservation to snag a seat.
If you're up for a challenge, the members-only Pub at the University of Chicago is right up your alley. To get there, you'll walk into Ida Noyes Hall with the confidence of a college kid, turn left and go down the stairs. You'll be deposited in a nondescript hallway, to the right of which is the Pub. The bar itself has a tiny entrance, so "sneaking" in is truly impossible. Instead, stand outside and wait for members to arrive and politely ask a friendly face to be your escort in. It'll cost you a $3 cover and a peek at your ID. Just be sure to buy your host a beer once inside as a token of your gratitude. But believe us, the beer selection and the nachos are worth it.
Named for the attempted bribe of former Cubs pitcher Mordecai Brown by the Black Hand Mob, Hush Money is a stylish cocktail den above Mordecai in Wrigleyville. In addition to a plentiful roster of beer (this is Wrigleyville, after all) and a curated wine list, the menu flaunts creative cocktails that are rooted in seasonal flavors. As a boozy bonus, fans of rare spirits can peruse one of the country's largest selections of collectible vintage liquors.
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. A highlight of the menu is the daiquiri program, which allows patrons to select one of four house rum blends, which are mixed and poured tableside over hand-shaved ice.
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.
There's only one way to get into Janitor's Closet, a secret speakeasy that's hidden inside boutique hotel FieldHouse Jones. Guests walk through the hotel lobby and take a staircase to the lower level before entering a door marked "Employees Only." Once inside, curiosity seekers are rewarded with intriguing cocktails and an ultra-intimate setting. The aptly named bar is housed inside an actual former janitor's closet, a relic of the building's past as Borden Dairy Depot. Janitor's Closet has just 15 seats, including stools at the bar and booths made to look like seats from an old school bus. The interior design goes the extra mile, with antiques from flea markets and thrift shops, Pine-sol boxes, shaggy mops and vintage paint canisters.
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 saddling 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 is open Thursday through Saturday, slinging classic cocktails and hearty bites from upstairs. Pro tip: Though you can't make reservations at the Library, you can reserve a table at Gilt Bar and ask to be seated downstairs.
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.