How to Get Into Chicago’s Best Speakeasies and Secret Bars
From celebrity chef-backed cocktail dens to bonafide Prohibition-era holdovers.
It’s been nearly a century since Prohibition ended, but speakeasies nowadays are as popular as ever, and clandestine bars all over the world are partying like it’s 1933. The key difference, of course, is that speakeasies no longer operate out of discreet necessity, but rather as a fun way to differentiate, play coy, and dabble in eccentric themes and offbeat locales—like parking garages and adult video stores. While some speakeasies are so popular that the inevitable line down the block debunks the intended secrecy, there’s still something enchanting and appealing about disappearing into a sign-less watering hole. In Chicago, a city with a long history of secretive boozing that dates back to the Capone era, speakeasies are as integral to the local bar culture as Malört. Old and new, and with varying degrees of blatantly obvious popularity, these hidden haunts can be found across the city, nestled underground, down alleyways, and behind barbershops. Here are the best hidden bars in the city, as well as what you need to know about how to find them.
Chinatown
Chicago’s Chinatown has long been a haven of soup dumplings and chili chicken, but craft cocktails? Not so much. That all changed earlier this year, when Nine Bar emerged as the neighborhood’s first cocktail bar, a dimly lit speakeasy nestled behind Moon Palace Express. Housed in what was once a dining room for the restaurant, the alluring bar is marked only by a blink-and-you’ll-miss-it sign that bears the Chinese characters for “Nine Bar,” which gives way to a sexy den filled with lounge chairs, stools, a DJ booth, and flashes of neon. This being Chinatown, look for Chinese-inspired tipples and spirits, including lots of highballs, sakes, and a masterful Mai Tai made with almond cookie orgeat. Come hungry too, ‘cause the snackable food menu is packed with heavy-hitters like mapo hot fries, a McKatsu fried pork sandwich, and crispy cauliflower in Chinese orange sauce.
How to book: Nine Bar does not take reservations, so arrive on the earlier side (pre-7 pm) to stake out a seat.
Portage Park
With a name like Nightshade, it’s safe to expect a bar with as much mystery as an Agatha Christie whodunit. Hidden below its sister bar, Moonflower, Nightshade is a subterranean newcomer in Portage Park, a neighborhood whose culinary clout has been on the rise of late (looking at you, Bluebird, Hot Dog Box, etc.). Open only on Fridays and Saturdays, it’s a sultry nook filled with cozy couch-clad corners, flickering tea candles, soft lamps, and strong drinks. With an entirely different menu from upstairs, options down here include signature shaved ice drinks, including a nightcap-worthy Pineapple Boulevardier, and bracing originals like the Up All Night, a caffeinated quaff of cold-brew, vermouth, tonic syrup, elderflower, Topo Chico, and orange oil.
How to book: Neither Moonflower nor Nightshade take reservations, so your best bet is to have a casual dinner upstairs and then mosey down.
Logan Square
A stark antithesis to the bright and cheery confines of Lonesome Rose, Logan Square’s mod Mexican hot spot that achieves Wes Anderson levels of pastels and photogenic twee, Golden Teardrops is the decidedly darker sister bar located behind the back of the restaurant and down a short set of stairs. You may need to adjust your eyes before finding a seat at the long L-shaped bar, because the space is so dark it feels like a haunted house—but instead of zombies and killer clowns, it’s hipsters and Tinder dates. Most of the light source comes from the “Weddings & Funerals” sign glowing behind the bar, the source for booze-forward beverages like Boulevardiers and Canadian Cocktails (essentially a maple-splashed Old Fashioned).
How to book: Golden Teardrops does not take reservations, but your best bet for finding a seat is on Wednesdays and Thursdays. Just rely on your other senses to help navigate the space and find a seat.
River North
One surefire sign that speakeasies are as mainstream as ever is the fact that the genre now boasts a basement bar slinging Jamón Ibérico-infused cocktails from one of the most famed chefs on the planet. Pigtail is a Spanish-influenced hideaway from José Andrés, a world-renowned chef/superhero who added the subterranean expansion after bringing Jaleo to River North and deciding that Chicago needed more Ibérico fat-washed Negronis in its life. Intricate, elaborate, and often hammy, cocktails are served up in a sophisticated, sleek room alongside equally porcine plates like ham tartare and fried pig ears. Feeling extra? This is one speakeasy that offers multi-course food and cocktail pairings.
How to book: Reserve via Tock.
Logan Square
Perfectly indicative of a speakeasy’s innately romantic ambience, Soif Wine Lounge is prettier and more colorful than those typically dark dens, a sentiment marked by the neon glow of the words “Soif de Vivre” at the foot of a flight of stairs. Tucked away in the basement of Testaccio, this chic nook puts the spotlight—or rather, the neon pink light—on French wine, with a velvety atmosphere designed to whisk guests away to a Parisian parlor. It’s an intimate oasis with seating for just 26, making this a prime spot for dates looking to swoon over a bottle of Champagne and a plate of salmon rillettes.
How to book: Reserve via Resy.
River North
When it first opened its hidden alleyway door in 2013, at the forefront of the nationwide tiki renaissance, Three Dots and a Dash quickly cemented itself as one of the most quintessential bars in the country. That’s thanks as much to its masterful mixology, its immersive Pirates of the Caribbean-esque atmosphere, and its groundbreaking premise—guests follow a series of flickering tiki torches down a River North alley, then enter an unmarked door into a long hallway lined with glowing skulls. It all culminates in a sprawling windowless room that feels more Disney World than Chicago, albeit decidedly more adult. Rum-centric drinks are served in elaborate—and highly sought-after—tiki mugs, along with gussied-up Polynesian faves like crab rangoon and spring rolls. Doubling down on the secrecy, Three Dots added a speakeasy-within-a-speakeasy, The Bamboo Room. It’s a far more intimate and subdued space, where beverage director Kevin Beary can spotlight more refined drinks anchored by esoteric rums and rhum agricoles.
How to book: Reserve via Tock.
Loop
Speakeasies have come a long way since Prohibition, when the bill of fare was low-rent hooch chugged in a dark corner. Case in point: It’s the year 2022 and you are free to spend $100 per cocktail at an eight-seat “micro bar” across from Millennium Park. That’s the M.O. at Milk Room, a tiny splurge-worthy speakeasy hidden behind frosted glass doors on the second floor of the Chicago Athletic Association hotel. Here, dapper mixologists work with some of the rarest, vintage spirits in the world, ensuring your Manhattan will be as life-changing as it will be expensive.
How to book: Reserve via Resy.
Wicker Park
This long-running den of sneaky delights is perched atop a red stairwell via an unmarked door above Mama Delia on Division, and does it ever take its speakeasy bonafides seriously. With live acts including fire eaters and burlesque performers, Bordel seeks to bring the energy of a sultry night in Paris to the mean streets of Chicago for a night of romance and intrigue. Bonus? Boozy punch served in fancy French tea sets—just try not to break anything.
How to book: Reserve via Resy.
Fulton Market
Alcohol and skin fades have always seemed to go pretty well together—as long as the customer’s the one doing the drinking. Turn your next haircut into something to actually get excited about at this dimly lit little gem tucked away behind an actual working barber shop. You don’t need to book a trim to get inside, but it certainly couldn’t hurt. As an added incentive, it’s located across the street from The Office, another local speakeasy gem, making for the easiest mini-bar crawl imaginable.
How to book: Reserve via Tock.
Pilsen
There are roughly three times as many actual aldermen on the Chicago City Council as there are seats at this supremely intimate (we’re talking 16-seat intimate) new bar-within-a-bar at the ever-hip Pilsen Yards. Plush velvet banquettes? Check. Classic cocktails served from Chicago’s most highly awarded mixologist, Lance Bowman? Check. You? If you’re lucky.
How to book: Reserve via OpenTable.
Loop
This more-touristy speakeasy offers everything you might expect when imagining such a venue, including something you might not: karaoke. The entrance is technically signless, but the large neon martini glass in the window is a dead giveaway to those who might be stumbling around the Chicago Board of Trade in search of booze for some odd reason. Hey, to each their own.
How to book: Stop by for first come, first served seating.
Wicker Park
We know, we know. Everyone and their uncle’s in on the “secret,” mural-strewn Damen Avenue entrance to this longtime cocktail hideaway. But while this Wicker Park institution may fall on the more obvious side of the speakeasy spectrum, it’s still difficult to unearth a better cocktail in the city. Sleek curtains and a sense of decorum round out this bucket list-worthy (or should it be coupe list-worthy?) mixology experience.
How to book: Reserve via Tock.
Andersonville
If you like your secret cocktail speakeasies served with a side of close-up magic, this absurdly unique performance space has your number. Enter through the laundromat to discover a large theatre space where shows like Music & Magic (music on stage, magic at your table) are doing their part to make sleight of hand illusions cool again. You don’t need a ticket to the show to hit the bar, where they’re slinging drinks like How Houdini Died and Sleight of Hand alongside small plates including Toulouse sausage boards and pork belly sliders. Knock back a few then head up the road to classic Andersonville hangs like Hopleaf and Simon’s.
How to book: Stop by for first come, first served seating, or purchase tickets for a show in the theater via the Chicago Magic Lounge website.
River North
The Green Door Tavern is a historic watering hole with a notably vintage vibe. And beneath it you’ll find The Drifter, which somehow actually feels even more vintage. That’s because it wasn’t designed as a speakeasy—it’s an actual, real-deal speakeasy left over from the tragically thirsty days of Prohibition. Restored to a sparkling sheen, this subterranean escape offers a rotating list of over 100 cocktails presented on Tarot cards alongside quirky entertainment that runs sporadically throughout the evening. Enter the Green Door Tavern, walk through the bar and down the back stairs, and you’ll come to a waiting room. (Capacity is 37, so emphasis on the word “wait.”)
How to book: Stop by for first come, first served seating.
West Loop
Located in Sushi Dokku’s basement, Booze Box is a dark and sexy bar where you’ll find Eastern-inspired drinks like Japanese highballs served alongside Japanese “trail mix” and a laid-back vibe. Hip-hop on the speakers is pretty common and the sultry lighting emanating from red lanterns makes this a great spot for a date night and/or million-dollar diamond heist planning session. Two words: sake flights.
How to book: Reserve via Tock.
Lakeview
On the exterior wall of Matilda bar, there’s a curious sign that simply reads “Baby Atlas.” While it sounds like a clothing line for plus-sized toddlers, it’s actually the turnt-up basement lounge that pumps the vibes every Friday and Saturday night. A night-and-day difference from its upstairs neighbor, Baby Atlas is a small, loud boozery where you’ll probably have to shout-talk, but also probably won’t even care because you’ll be busy CRUSHING IT like a Beyoncé backup dancer. Lace up your dancing shoes, stroll inside Matilda, find the stairs in the back of the bar, and head on down.
How to book: Stop by for first come, first served seating.
Irving Park
The Fifth Province is a traditional Irish pub, but its positioning is about as traditional as wearing clown shoes to a non-clown wedding. Located in the southern wing of the Irish American Heritage Center, the pub is completely hidden from view. The building itself looks very much like a local high school, so finding a bar inside really makes it seem like you’ve stumbled upon an after hours teacher’s lounge. Enter through the main doors of the center, take a left and head down the hall. (It can also be accessed via the pub doors.)
How to book: Stop by for first come, first served seating, or book the whole place for a private event via their website.
Lakeview
With a discreet alleyway entrance just to the left of the Old Chicago Inn, this is perhaps the most “secret” bar in town, literally. To get in, you can either apply for membership for a yearly fee or earn an invite by staying at the hotel (where special cocktail flight packages are also on offer.) Your reward? Mixology-perfect drinks from the 1920s (did someone say Manhattan?), served with a healthy side of historical insights. All they ask is that you dress decently, for once in your life.
How to book: Request a reservation online.
West Loop
Located below The Aviary is one of the most exclusive rooms in town. The entrance to this Grant Achatz-backed den of high-priced cocktailery requires an advance reservation, but is well worth the effort if you’re looking to impress someone with your expert taste in classically inspired cocktails served with rare, antique spirits. Can’t decide? Order a dealer’s choice and let the supremely qualified barkeeps do the work for you.
How to book: Reserve via Tock.