While the term "speakeasy" has been so overused that it’s devolved into little more than marketing, it’s always fun to feel like you’re in on a secret. And in a city like Chicago with such a rich history of illicit hooch, the possibilities for a little good old-fashioned bar mystery remain as plentiful as disappointed Bears fans on Sunday. These “secret” Chicago “speakeasies” may make you work a little harder to find them, but that’s all part of the fun. Here are the best hidden and speakeasy-themed bars in Chicago, with tips on how to get into them.
This Valentine's Day Milkshake Is Topped With a Slice of Red Velvet Cake
Logan Square Chicago has a new Red Light District. It starts and ends in the back of the bakery next to Fat Rice, where a small red-lit room of saucy Cantonese delights tugs at the heartstrings with vintage Asian pin-up art on the walls, drinks with names like The Bizarro Jerry and Run the Jewels, and flaming bowls of booze including the notorious Burning Bird. The intimate space only seats about 20, so you’ll most likely need a reservation. Might we suggest the crucial third date with that cute new co-worker? Hard to find a better closing act in the city. How to get in: Enter through the bakery.
Wicker Park We know, we know. Everyone knows the “secret” entrance to this longtime cocktail speakeasy can be found by locating the door handle in the mural along Damen Avenue. (Well not everyone, but you get the idea.) But while this Wicker Park institution may be on the more well-known 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 rocks glass list-worthy?) mixology experience. How to get in: Located the door handle in the mural along Damen Avenue.
Loop It doesn’t get much more exclusive than this intimate eight-seat “microbar” on the second floor of the Chicago Athletic Association, which was once used as an actual speakeasy during Prohibition. With a beverage program helmed by local bartender extraordinaire Paul McGee, Milk Room is serving up exactly the type of spirit-forward cocktails you would expect, featuring rare vintage elixirs and a deep whisky selection. Knock bar a few and then head upstairs to Cindy’s for more cocktails overlooking Grant Park as you survey the scene like Gordon Gekko. How to get in:RSVP here.
Andersonville If you like your secret cocktail speakeasies served with a side of close-up magic, this new performance space could be just your ticket to a weird night of fun. Enter through the laundromat to discover a large theatre space where shows like David Parr’s Cabinet of Curiosities are doing their part to make magic 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 Publican 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 get in: Enter through laundromat.
Hyde Park Located in the gorgeous Ida Noyes Hall on University of Chicago’s campus, The Pub is a historic bar that looks like the kind of place Harry Potter and all his broom-riding wizard friends would hang out. Also: students, faculty, and staff of the university, because those are the only people who can buy a membership to this private club. If you manage to tag along with a member, inside you’ll find old-timey photos, 28 beers on tap, and mixed drinks in pint glasses -- plus pub grub and “goblets” of Lagunitas, New Belgium, Stone, and North Coast ales, if you’re into that sort of thing. How to get in: Find a member, follow them to The Pub (with their permission, obviously), and once you get there, purchase a visitor’s day pass for $3.
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-ier. That’s because it wasn’t designed as a speakeasy: It’s an ACTUAL speakeasy from the tragically thirsty days of Prohibition. Restored to a sparkling sheen, The Drifter offers a rotating list of over 100 cocktails presented on Tarot cards and quirky entertainment that includes burlesque shows curated by Michelle L’amour. How to get in: Enter the Green Door Tavern, walk through the bar, head down the stairs in the back, and you’ll come to a waiting room. Capacity is 37, so you may have to wait a bit.
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” snacks and a laid-back vibe. Hip-hop on the speakers is pretty common and the sexy lighting illuminated by red lanterns makes this a great spot for a date/million-dollar diamond heist planning session. Two words: sake flights. How to get in: Head to the alley located just south of Sushi Dokku and find the door with a Booze Box sticker near its handle.
River North River North has plenty of loud spots that are about as wallet-friendly as a munchies-induced visit to Whole Foods. Watershed is not one of them. This subterranean lounge is definitely a looker, and the comfy booths and sofa seats have a tendency to make time melt away. You won’t mind one bit though, since the cocktails here are great and a $6 Old Style-and-Bulleit-bourbon shot special is available daily. They’re also serving up a wide range of snackables from steak tartare and brisket sliders to deviled eggs and chocolate brownies. How to get in: Head into Pops for Champagne and find the stairs in the Southeast corner of the bar.
Rogers Park Unlike other student-frequented bars that you're not allowed to go to anymore, we fully encourage you to check out this unique drinkery located in the basement of Loyola University Chicago’s Damen Student Center. It’s actually a student-run operation, and the ones working here are getting hands-on experience on how to run a full-blown bar. Expect a menu of pizzas and paninis, rotating tap brews, and a few communal tables. It’s also a solid spot to grab a beer before, during, or after a (reigning Final Four champion!) Ramblers basketball games. Non-boozers or youngins are also welcome to hang as long as they stick to sipping the pub’s French press, drip, and cold brew coffee. How to get in: Find the stairs next to the food court inside the Damen Student Center and head down. Also, the bar is closed when school isn’t in session.
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 lounge located in the basement of Matilda open Friday and Saturday nights. 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. How to get in: Walk inside Matilda, find the stairs in the back of the bar, and head down.
Irving Park The Fifth Province is a traditional Irish pub, but its location is about as traditional as wearing clown shoes to a non-clown wedding. Located in the South wing of the Irish American Heritage Center, the pub is completely hidden away from plain 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 a Stonemasons hangout. In addition to hearty pub fare and pints of Guinness, you can expect live music on weekends after 8 p.m. How to get in: Enter through the main doors of the center, take a left and head down the hall. (It can also be accessed through the pub doors.) The bar has limited hours, however: Tuesdays and Thursdays from 6 p.m.-10 p.m.; Fridays and Saturdays from 6 p.m.-1 a.m.
Lakeview With a discreet alleyway entrance just to the left of the Old Chicago Inn, this is perhaps the most traditionally “secret” bar in town. To enter, you can either apply for membership for a yearly fee or earn an invite by staying at the hotel (where “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. Open Wednesday-Saturday from 5 p.m.-1 a.m., all they ask is that you dress decent. How to get in: Apply for a membership at the Old Chicago Inn, or book a room there.
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 cocktail art requires an advance reservation, but is 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 bartenders do the work for you. How to get in: RSVP here.
Logan Square If you define “secret” as “not having a sign,” this Logan Square hotspot fits the bill nicely, with nothing but a black alley door and red light enabling you access to a dimly lit lair of exposed brick, black curtains, and ubiquitous PBRs. But it’s not all dark and brooding inside, as you can also grab a wooden picnic table on its bright outdoor patio space surrounded by graffiti art during warmer months. Stop by for live bands and DJs most nights as well as regular tequila and punch specials. How to get in: Locate the nondescript side entrance off Medill, and look for the red light above the door, which is lit when the bar is open.
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Raf Miastkowskialways likes to divulge secrets to thousands of people at a time. Send him your most-guarded tips @RafFoSho.