Chicago

13 Things to Do in Chicago After Dark

See a different side of the city with these fun nighttime activities in Chicago.

BigPineapple/Shutterstock
BigPineapple/Shutterstock
BigPineapple/Shutterstock

Chicago may not be the city that never sleeps, but it’s definitely a night owl. By day, this world-class metropolis dazzles with museums, boat tours, buzzy brunches, and daredevil skyscraper attractions, but after dark, the city comes alive in a whole new way. Under the twinkling glow of one of the best skylines in the world, twilight is a time for luminous boat rides, sexy speakeasies, and radiant art shows. Far beyond the confines of Chicago’s soaring downtown, after-bedtime attractions can be found throughout its neighbourhoods, from clandestine magic shows and intimate improv sets to bars crawls, 24-hour taquerias, and al fresco movies. Whatever your fancy, this is one city worth staying up late for, as evidenced by these 13 things to do in Chicago after dark.

The Adler Planetarium
The Adler Planetarium
The Adler Planetarium

Linger a little later at the Adler Planetarium

South Loop
In case you’ve ever wanted to pull a Night at the Museum at the Adler Planetarium, you’re in luck. Adler at Night is a weekly late-night series, for adults only, which extends hours well past normal closing time, to allow for a different experience after the sun sets. Every Wednesday, the Museum Campus planetarium is open until 10 pm, offering special sky shows, experiences, and activities that make it sound like the dreamiest date night for science-lovers and stargazers. Added bonus: It’s free to attend for Illinois residents, so it’s also a cheap date night.

The Underground Cocktail Club
The Underground Cocktail Club
The Underground Cocktail Club

Pair sexy sushi with a sexy speakeasy

River North
For that quintessential see-and-be-seen downtown vibe, it’s hard to out-strut Sunda. Normally, sexy new Asian fusion restaurants like this one tend to lose their luster over the years, waning in popularity in the face of the hot new spot in town. But Sunda is as sexy, chic, and feverishly popular as the day it debuted in 2009. Still the hot ticket for a late-night feast of miso cauliflower, tuna truffle pizza, and pork adobo fried rice, it’s the prime launching point for a night out downtown-the nightlife-savvy restaurant group, Rockit Ranch Productions, recently opened The Underground Cocktail Club nearby, as a Roaring Twenties-inspired quasi-speakeasy, awash in rose gold fixtures and sultry feathers. Complete with jazzy live music, high-end cocktails, and enough Champagne to cater a Royal Jubilee, it’s the kind of place you can linger until the wee hours (4 am on Fridays and 5 am on Saturdays).

Mercury, Chicago's Skyline Cruiseline
Mercury, Chicago’s Skyline Cruiseline
Mercury, Chicago’s Skyline Cruiseline

Set sail after sunset

Chicago River
With its sea-sized lake and iconic-and occasionally infamous-river, water activities are a prime attraction in Chicago, and we’re not just talking about beach volleyball with college bros on North Avenue Beach. Boat tours are an incredible way to drink in the skyscraping sights from a stunning vantage point, especially as guided excursions weave along the Chicago River through a veritable canyon of world-class architecture. At night, the sights take on a totally new twinkle. Companies like Mercury Cruises offer night cruises along the river and lake, featuring bar snacks and drinks, along with insightful commentary along the way. Sailings depart from the Chicago Riverwalk around 8:15 pm through October, so you’ll get to see the city aglow in the sunset before things get dark and the buildings light up like 70-story Christmas trees.

Velvet Taco
Velvet Taco
Velvet Taco

Go on a twilight taco crawl

Various locations
Chicago has so many incredible taquerias, that it’s impossible to try them all in the span of a day. Fortunately, several are open later than most nightclubs, so you need not confine your carnitas cravings to the daylight. Try the hulking burritos and al pastor tacos at Humboldt Park staple Birria Huentitan Restaurant (open until 2 am), keep the party going with margarita pitchers and lengua tostadas at 24-hour Arturo’s Tacos in Bucktown, go bougie with Nashville hot tofu tacos and red velvet cake at Velvet Taco in the Gold Coast (open until 3 am on weekends), or chow down on chips and juicy chicken tacos at Chavas Tacos, a 24-hour Ukrainian Village taqueria with the cozy look and feel of an all-night diner.

Zanies Comedy Club Chicago
Zanies Comedy Club Chicago
Zanies Comedy Club Chicago

Enjoy some late-night laughs at hallowed comedy venues

Various locations
Home to The Second City, Zanies, and the iO Theater, Chicago has long been a keystone for comedy in the US. And since the idea of seeing a crass stand-up set in the middle of the afternoon seems weird, most of said comedy takes place after dark. In addition to the aforementioned hallowed venues, which regularly feature big comedic acts, Emmy-worthy improv, and special shows, Chicago abounds with more indie comedy halls throughout the city. Places like The Comedy Clubhouse in West Town, The Lincoln Lodge in Bucktown, Annoyance Theatre in Lakeview, and The Comedy Bar in Streeterville are all great places for a more intimate, affordable experience-and the exciting chance to spot up-and-coming talent before they ascent to Tiny Fey levels of fame.

Chicago Magic Lounge
Chicago Magic Lounge
Chicago Magic Lounge

Mix magic with mixology at the Chicago Magic Lounge

Andersonville
Describing itself as part speakeasy and part magical theatre, the Chicago Magic Lounge is a singular experience that’s truly worth staying up late for. With Harry Potter-levels of trickery and whimsy, the clandestine adults-only lounge is located in a converted laundry building from the ‚Äė40s, which has since been transformed (presumably via magic wand) into a Vaudeville-inspired space with a performance bar, cabaret theatre, and the intimate 654 Club, all offering sleight of hand magic and parlour tricks, from dapper magicians with an apt flair for the eccentric. Tinged with plenty of comedy, the venue also offers small plates, wine, and cocktails, with events and hours lingering well after dark-until 2 am on weekends.

Art on the MART
Art on the MART
Art on the MART

See art on a grand scale

River North
Times Square, eat your heart out. While the neon lights of places like Manhattan and Las Vegas may be well-trod, if a bit touristy, Art on theMART is a luminous display like no other that emphasizes art over, say, a glowing pyramid hotel. Displayed nightly on the side of theMart (formerly the Merchandise Mart), a commercial building so mammoth it once had its own zip code, Art on theMart is the largest permanent digital art projection on the planet, casting contemporary displays across 2.5 acres worth of architecture. Best viewed from across the Chicago River, rotating musical shows are held nightly at 9 pm or 9:30 pm, celebrating everything from historic African American parade marches to a dance-filled performance art film by Nick Cave.

Chicago Park District
Chicago Park District
Chicago Park District

Pack a picnic for Movies in the Parks

Various locations
While summer days in Chicago can be downright scorching and drowning in humidity, evening brings a peaceful respite with warm breezes, breathable air, and wholesome activities like outdoor films. Movies in the Parks is an annual summertime go-to for Chicagoans, as the Chicago Park District transforms the city’s myriad green spaces into a veritable al fresco film festival. Free to attend, with multiple genres of family-friendly fare screened in parks across the city, all movies are projected on pop-up screens around 8:30 pm, giving the sun enough time to set and the movie stars time to shine. Peep the calendar for a movie near you all summer long-this year’s slate runs the gamut from Clifford the Big Red Dog in Rosenblum Park and The Princess Bride in Loyola Park to the latest Spider-Man in Augusta Park.

Outside Voices
Outside Voices
Outside Voices

Go on a bar crawl through Logan Square

Logan Square
Practically all Chicago neighbourhoods have their share of CTA-worthy bars, pubs, taverns, and dives, but perhaps nowhere is the drinking scene more dynamic-and worthy of a bar crawl-than Logan Square. The northwest side neighbourhood, conveniently accessed right off the Blue Line (so you can save money on regrettably tipsy Uber expenses), Logan Square is home to Instagrammable cocktail haunts like tropical Estereo, swanky Billy Sunday, tavern-inspired Spilt Milk, and The Heavy Feather, a retro-glam fern-filled bar above dance club Slippery Slope. The same folks behind the latter put the spotlight on wine at artsy, wood-filled bar Outside Voices, while Union is an impressive beer bar with an equally stunning food menu from the meaty minds behind nearby Lardon. The neighbourhood has its fair share of timeworn dives too, like Whirlaway Lounge and Bob Inn, while The Owl and Cole’s Bar are the kinds of dives with dance tunes. For an alluring speakeasy vibe, descend into Golden Teardrops, a nondescript basement bar underneath Lonesome Rose that’s so dark it feels like a haunted house that just happens to make a killer nightcap. If you’ve got room for one more, sip some whiskey at Longman & Eagle and then stumble upstairs, where the hipster tavern doubles as an inn with a few beautifully designed rooms.

Pequod's Pizza Chicago
Pequod’s Pizza Chicago
Pequod’s Pizza Chicago

Enjoy a deep-dish late-night snack

Lincoln Park
You never know when a sudden, undeniable hankering for deep-dish pizza is going to ensue, and when it hits, you don’t want to go hungry. Conveniently, one of Chicago’s best deep-dish spots is open long after the tourist traps shut down for the night, so the next time it’s 1 am and you’re dying for a whole pan-sized disc of sausage, head to Pequod’s. Known for its caramelized, cheese-lined crust, it’s a pizza icon that’s perfected the form in Chicago, and become a go-to icon for connoisseurs near and far. The dimly lit, tavern-esque pizzeria in Lincoln Park is open until 2 am most nights, in case you want to take your late-night snack situation to the next level.

Snakes & Lattes
Snakes & Lattes
Snakes & Lattes

Play board games until midnight

Bucktown
Game night just got a glow up, thanks to Bucktown’s Snakes & Lattes, a self-described board game restaurant featuring various themed rooms, a full menu of snackable treats, trivia nights, and all the board games-new and old-that you could dream of. The main floor is home to the game library, with more than 3,000 to choose from for on-site play (and another 1,000 available to purchase and take home), while immersive private rooms are themed so as to make you feel like you’re playing on an Italian terrace or in a pastoral forest. Open until 11 pm on Wednesdays and Thursdays, and until midnight on Fridays and Saturdays, with a full food menu of Americana plates, you’ll have plenty of time to bankrupt your friends at Monopoly.

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Matt is a recent transplant to Oklahoma City after two and a half years of RV living, Matt Kirouac is a travel writer working on a memoir about the epic ups and downs from life on the road as a gay couple-and the lessons learned along the way. Follow him on IG @mattkirouacofficial.

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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