12 Things to Do in Chicago After Dark

Compared to other sleepless cities, like Las Vegas and New York, Chicago may not be the most obvious destination for late-night revelry, but the Second City is really second to none when it comes to past-your-bedtime fun. During the day, this mighty metropolis is well known for its world-class museums, festivals, shopping, parks, and restaurants. Come sunset, the city continues to awe. Under the twinkling glow of one of the country’s best skylines, you’ll find all manner of activities and attractions worth staying up for, from bougie billiards and after-hours museums to sleight of hand with a side of goat cheese. The all-night entertainment isn’t confined to summer, either. Just because the winter weather outside is often frightful doesn’t make nightlife in Chicago any less action-packed—plus there’s the added bonus of “after dark” in winter meaning “any time after, like 4:30 pm.” Which means more time to partake in any of these 12 things to do in Chicago after dark.

Loop
Bocce gets a serious glow up at Game Room, a retro-chic billiards bar nestled inside the Chicago Athletic Association hotel downtown. A far cry from the endearingly dusty dive bar stereotypes, this modestly dubbed bar is a sprawling adult playground filled with classic games like bocce, chess, shuffleboard, and checkers—all served up with food and drink menus that go far beyond the call of checkers duty. Owned by the same folks behind some of Chicago’s most beloved late-night haunts, like Parson’s Chicken & Fish and Lonesome Rose, you’ll find crowd-pleasing snacks like Parson’s fried chicken sandwiches, Lonesome Rose beef tacos, whitefish patty melts, and foot-long hot dogs, plus frozen Malort cocktails (if you know you know) and other classic-inspired tipples. It’s game on until 11 pm Monday - Thursday, and until 2 am Friday - Saturday.

Ukrainian Village
Late-night live music is a rite of passage in Chicago, and while there are always new venues popping up all over town, there’s always something nostalgic about revisiting an old haunt. For the most heartwarming, intoxicating blast from the past, head to the Empty Bottle, a Ukrainian Village institution that’s been pumping out live shows and dirt-cheap beer since 1992. Today, the gritty corner bar is still as popular as ever, the drinks are practically as cheap as ever, and many shows are still free. Its dark and cozy confines make it particularly apt for a winter night, and as an added bonus, barflies can order Sicilian-style pizza from adjoining Pizza Friendly Pizza.

Avondale
The calendar may say 2023, but it still feels like the ‘70s at Avondale Bowl, a new-ish retro-inspired bowling alley that combines elevated cocktails with vintage aesthetic and Big Lebowski vibes. 21+ after 7:30 pm, the eight-lane venue is open until midnight nightly, and until 1 am on Fridays and Saturdays. At once old-school (each lane is manual scoring) and newfangled, this is the kind of bowling alley that combines Old Style and local craft beer on draft, along with a deep whiskey list and cocktails that are worth the price of admission alone. The Dude would approve of the frozen White Russian, served slushy-style with vodka, coffee liqueur, coconut cream, and oat milk.

Various locations
Combining theater and comedy with scantily-clad sex appeal, drag shows are a singular type of entertainment that pairs equally well with late-night debauchery as it does with mimosas. While the epicenter of drag culture is still anchored in LGBTQIA-centric neighborhoods like Northalsted, drag shows are now ubiquitous throughout Chicago, which means you’re never more than an “L” stop away from gender-bending theatrics. Some iconic spots include The Baton Show Lounge in Uptown and Lips, a South Loop dinner show staple where guests can dine on grilled salmon while playing “Bitchy Bingo.” In Northalsted, the most historically queer neighborhood in town, cornerstones like Kit Kat Lounge & Supper Club, Sidetrack, Berlin, and Roscoe’s Tavern feature drag shows well past the witching hour.

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 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.

Fulton Market
If your idea of late-night snacks includes Vietnamese duck wings, Wagyu skewers, and $2,000 worth of caviar, then After is the after-dinner bar of your dreams. Designed as a kind of decadent digestif for its adjacent sister restaurant, the Michelin-starred tasting menu temple Ever, you’d expect nothing less from one of the most acclaimed chefs in town. The posh lounge is the handiwork of chef Curtis Duffy and Michael Muser, who’ve put together a gorgeous space with equally gorgeous drinks and small plates. Along with a curated menu of cheffy nibbles, the deep cocktail list offers something for everyone—classic cocktails like Manhattans, calamansi-infused Cosmos, and the prettiest Margarita you’ve ever seen share menu space with spirit-free drinks, rare spirits, and original creations like Fig Sazeracs and coconut-kissed Haitian Daiquiris. The lounge is open until midnight Tuesday-Thursday, and until 2 am Friday - Saturday.

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 offbeat small plates like baked goat cheese and potato pancakes, along with wine and cocktails, with events and hours lingering well after dark—until 2 am on weekends.

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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