13 Things to Do in Chicago After Dark

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 neighborhoods, 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.

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.

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).

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.

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.

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.

Andersonville
Describing itself as part speakeasy and part magical theater, 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 ‘40s, which has since been transformed (presumably via magic wand) into a Vaudeville-inspired space with a performance bar, cabaret theater, and the intimate 654 Club, all offering sleight of hand magic and parlor 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.

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.

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.

Logan Square
Practically all Chicago neighborhoods 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 neighborhood, 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 neighborhood 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.

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.

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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