Chicago

How to Get Into Chicago's Best Speakeasies and Secret Bars

From celebrity chef-backed cocktail dens to bonafide Prohibition-era holdovers.

Bordel Chicago
Bordel Chicago
Bordel Chicago

While the term “speakeasy” has arguably been so overused it’s devolved into little more than a marketing ploy, feeling like you’re in on a boozy secret remains undeniably irresistible. And in a city like Chicago, with our rich history of illicit hooch, opportunities to pair your booze with a smidge of mystery run as rampant as disappointed Cubs fans at the trade deadline. It might take a little extra work to track down these “secret” Chicago bars, but, hey, 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.

Bordel Chicago
Bordel Chicago
Bordel Chicago

Bordel

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.

Blind Barber
Blind Barber
Blind Barber

Blind Barber

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.

The Alderman
The Alderman
The Alderman

The Alderman

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.

Brando's Speakeasy
Brando’s Speakeasy
Brando’s Speakeasy

Brando’s Speakeasy

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.

The Violet Hour
The Violet Hour
The Violet Hour

Violet Hour

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.

Chicago Magic Lounge
Chicago Magic Lounge
Chicago Magic Lounge

Chicago Magic Lounge

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 slight 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.

The Drifter Chicago
The Drifter Chicago
The Drifter Chicago

The Drifter

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.

Booze Box
Booze Box
Booze Box

Booze Box

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.

Matilda & BabyAtlas
Matilda & BabyAtlas
Matilda & BabyAtlas

Baby Atlas

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 neighbour, 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 Beyonc√© 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.

Irish American Heritage Center
Irish American Heritage Center
Irish American Heritage Center

The Fifth Province

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.

Old Chicago Inn featuring Room 13
Old Chicago Inn featuring Room 13
Old Chicago Inn featuring Room 13

Room 13

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.

The Aviary
The Aviary
The Aviary

The Office

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.

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Raf Miastkowski always likes to divulge secrets to thousands of people at a time. Send him your most-guarded tips @RafFoSho.

Jay Gentile is a Thrillist contributor and equally terrible at keeping secrets.

Chicago

Robyn DaCultyre Is Doing It for the Culture

"The cool thing about Ohio is that there is literally a place for everyone."

Photo by Kayode Omoyosi
Photo by Kayode Omoyosi
Photo by Kayode Omoyosi

I was introduced to Robyn DaCultyre at an Untitled Queen show at C’mon Everybody in late January, and it was one of the most unique drag shows I’d seen in a while. Afterwards, I tracked down this self-described “drag creature” and video chatted about her drag origin story, the state of drag in her native Ohio, and the dual identities that make up her persona. Thrillist: I want to ask you about how Robyn DaCultyre came about and your point of view behind your performance.

Robyn DaCultyre: I’ve been travelling around the country from a young age in ministry and Christian studies. I moved to Chicago right after high school. Four years later, moved back to Columbus and decided I didn’t really want to do church anymore; that wasn’t where my heart was.

I had a really low point in my life and had a suicide attempt and then really found drag and started doing drag as a coping mechanism and way to let off steam. I started in July of 2019, and it was really a lot of punk and metal music. I created this drag creature of sorts and they were really out of this world and celestial and all of those fun alien type terms.

And then we went into a global pandemic and I had a lot of time to figure out who I wanted to be. Digitally I was still doing a lot of drag creature-esque numbers and all of that, but I had this moment where we’re on the front lines getting hit with pepper spray and rubber bullets and pepper spray-all of those lovely things. And I said, I have this platform and I need to start showcasing what’s happening.

Untitled [Queen] stepped in at the right time and messaged me and said, “I’m doing this show for Independence Day called Untitled in America with 52 different performers and I want you to be a part of it.” It was at that moment I was able to take the footage I had been recording on the front lines and incorporate it into digital content. I did a song called Black Like Me by Mickey Guyton that talks about white picket fences, but if you want to see how America is, then you should try being Black like me. The imagery of what’s literally happening in Columbus in that digital performance really spearheaded me into focusing on people who look like me.

Nina Simone is one of my biggest inspirations, and one of her quotes that resonates with me is that it’s the duty of the artist to resonate with the times. My art is politically charged. I like to entertain, but there will definitely be a time when you come to a show expecting to have your drink and be chill and that might not be the case.

How did the name Robyn DaCultyre come about?

I was smoking with Ursula Major, who was on season one of Dragula, and the first time I introduced myself to her I was Robyn Banks, which is my drag name originally. She said, “Well, do you just not want to be original at all?” [Laughs] And I sat with that for a couple of months, and I got really stoned one day and was listening to Janelle Monae, and she talks about doing it for the culture, and I said “I do it for the culture, too!” And the rest is history.

And you started a series called Melanated.

We started Melanated last February. I told the idea to my show director that there were no shows specifically run by Black people that only featured Black entertainers. I wanted to do this show for a night and she said, Why don’t we do it once a week for the whole month? The first show happens, and it’s a sold out crowd, and [my director] comes back and says we should do this every month. So I sucked it up and here we are a year later.

Melanated is the only fully Black show in all of the state. It’s a horrible marketing tool and not something I want to promote, but it is just a fact. It amazes me that we are the 13th largest city in America and there’s nothing here that’s fully focused on Black entertainers. The name also comes from Janelle Monae; she says she’s highly melanated and I said, that works.

Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)

You refer to yourself as a drag creature, as opposed to drag queen or king…

This is actually the first time I’m making this public. I am in this place where I want to separate the alternative creature from who this melanated goddess or whatever is. DaCultyre is definitely the person who runs Melanated and then Robyn is this drag creature that is out of this world and really loves punk and alternative music. And both intertwine to make Robyn DaCultyre.

You also do pageants. Tell me about that.

In 2020 I was appointed by Nina West, who is from Columbus, as the representative from Ohio for National Entertainer of the Year in Louisville, Kentucky. I placed ninth out of 13 contestants and I really fell in love with the system and fell in love with the pageantry and loved the idea of reigning and being different. I want to show that we as alternative performers, as bearded performers, you can come into these systems and shake things up.

Is there a uniquely “Ohio” style of drag?

No, and I think that’s one of the things that makes it so amazing is that everyone has their own unique style, and it’s all pretty much accepted. I started as a performer and a drag creature and there was space that was afforded to me and I transitioned to more glamor and pageantry and that’s afforded to me as well. I’ve been a bearded entertainer for a year now. The cool thing about Ohio is that there is literally a place for everyone.

I think I have everything I need. Is there anything else I didn’t ask you about that you want to bring up, or‚Ķ

I don’t think so. Are there any generic questions you haven’t asked?

Generic questions‚ĶI think I asked all of them already [laughs]. I like to ask what you’d be doing if you weren’t doing drag?

It’s a great question. I have a day job that is very demanding so I need drag to get away. I’m also very creative and artistic. I used to do web design and all these other things to pull into my creativity. Drag is the longest thing I’ve stuck with in all parts of my life, so I don’t think it’s going anywhere anytime soon.

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John deBary¬†is a drinks expert and writer. His first cocktail book,¬†Drink What You Want, is available now, and his next book,¬†Saved by the Bellini, is expected in early 2023. He is also the co-founder and president of the¬†Restaurant Workers’ Community Foundation, which is dedicated to improving the lives of hospitality industry professionals through advocacy, grant making, and impact investing.

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