Chicago Nightlife: What to Do After Dark

We can’t all be early birds. Some of us come alive only after the sun sets, when it can be difficult to find things to do that are enjoyable, safe, and recurring. And let’s face it -- while we all love a good happy hour deal, it’s often impossible to leave work by 3, choose a bar, stake out a table, and order a drink before time mysteriously leaps forward and ruins all plans for discount daiquiris. But don’t fret, night owls. There’s plenty to do in Chicago at night, from trivia, midnight movies and art walks, to museum sleepovers, sword-swallowing, and -- gasp! -- even a late-night happy hour you can hit up without neglecting your to-do list. These are the best ways to keep entertained after dark in Chicago.

Spend the night in a museum 

Various locations
Or just visit one at night -- your choice. Basically, all the major museums in the city offer after-hours programming at select times during the year. You can have a legit sleepover with the family come winter during the Field Museum’s Dozin’ with the Dinos series, or ditch the kids for adult stargazing at Adler After Dark, which takes place every third Thursday of the month and is for ages 21 and up. The Shedd, Museum of Science and Industry, Museum of Contemporary Art, and Art Institute all have some type of nighttime offerings, so pick your cultured poison.

Sofar Sounds Chicago
Sofar Sounds Chicago

Discover your next favorite musician

It’s easy to get in a musical rut of listening to those same five songs on Spotify, but you just might discover your next favorite artist thanks to Sofar Sounds. Enter the lottery for a chance to purchase tickets and the day before the show, the performance location will be revealed. You might end up at a funky record shop or at someone’s swanky home (some shows are BYOB while others have cash bars), but it’s a great way to expand your music collection and catch a live show in a unique venue.

Check out a show from an artist you already know

It’s fair if you’d rather know which artist you’re seeing in concert and, luckily, the city is brimming with live concert venues. Hit up Reggies in the South Loop, Pilsen’s Thalia Hall, Aragon Ballroom -- excuse me, Byline Bank Aragon Ballroom -- in Uptown, or Subterranean in Wicker Park, just to name a few.

Dance shoes and drag shows

Berlin Nightclub
This late-night Boystown club opens at 8pm or 10pm, depending on which day you go, so it’s a top choice for night owls. Catch a drag show or just go for the DJ and dance floor -- the party doesn’t stop until 4am or 5am most days.

Actually, bar-hop in Boystown, period

Sure, lots of neighborhoods have multiple bars on each block, but in Boystown, you can go from a drag show at Berlin to bottle service at Sidetrack without missing a beat. If you’ve got time to spare and are up for a little adventure, wander up and down Halsted Street and see where the night takes you.

movie in the park
Chicago Park District

Catch a flick under the stars

The Chicago Park District has been hosting summer movies in parks all around the city for the past 19 years, so it’s a perfect movie date, whether you want to stay close to home or venture to another neighborhood. Catch an old favorite or the blockbuster from last year that you never quite got around to seeing -- movies are free so you won’t feel guilty about splurging on candy and snacks.

Have a night out in the Parks

The Park District’s summer movie series typically runs through the first week of October, but Night out in the Parks runs year-round. From roller skating parties to community bonfires to a midnight circus and stage play, there’s a variety of free or budget-friendly nighttime entertainment.

Test your trivia prowess

Who doesn’t like to brag about how smart they are over beer and a burger? Chicago loves trivia nights, with more than 100 different options in multiple neighborhoods throughout the year. Pop culture, history, sports, movies -- whatever you’re into, there’s a trivia night for that.

The Escape Game
Courtesy of The Escape Game

Plot your escape

Once upon a time, we relied on horror films and October haunted houses for our thrills, but why wait for Halloween when you can lock yourself in a room at any time of year? Trivia is fine and all, but if you want to get really competitive and flex your brain under duress, level up: Chicago has plenty of escape rooms to get stuck in.

chicago magic lounge
Chicago Magic Lounge

Capture a magical moment 

Chicago Magic Lounge
Magic shows aren’t just for kids anymore, especially when they’re presented with a side of booze in a lux space. There are various spots to catch a magic show in the city, but the Chicago Magic Lounge whisks you away the moment you enter through the faux-laundromat door. Have a cocktail and share a small bite or two as you settle in for an evening of illusion and mystery -- the lounge is open until 2am, Fridays and Saturdays. 

Visit a (quality) sex shop

Multiple locations
Whether you’re in the market for a new toy, want to stock up on lube or simply study up on the latest kinks, a stroll around the sex shop with an open-minded friend makes for a night full of laughs and maybe even a touch of pleasure. The Lincoln Avenue location of The Pleasure Chest is open till midnight and even offers workshops on topics like sex and disability, squirting, and pleasing the penis, while Early to Bed in Andersonville was founded with the mission of providing a safe space for folks of all genders.

Eat, drink, and sing in Chinatown

Chinatown is one neighborhood that never sleeps. Chi Cafe, for instance, is open until 4am during the week and 24 hours on Fridays and Saturdays. Even in the winter, you’ll spot people having bubble tea or ice cream, and if you’re not in the mood for food there’s always karaoke. Spots like Sakura Karaoke Bar and Zero Degree Karaoke Bar and Club are open until 2am or 3am.

Watch a midnight movie

Music Box Theatre
There are times for matinees, times for movies in the park and times for cult classics when the clock strikes 12. Around since 1929, the Music Box is a Chicago institution that hosts all types of events, including midnight showings of classics like The Room -- bring your own spoons! -- The Rocky Horror Picture Show, and other rotating features.

Chicago Arts District gallery
Chicago Arts District

Go on an art walk

The Chicago Art District’s 2nd Friday Gallery Night takes place every month, winter, spring, summer, or fall. How far you travel is up to you, as at least a dozen galleries usually participate, even though you could stay in one gallery drinking wine, eating small bites, and browsing various works from local artists for hours. 

Game time at the bar

Multiple locations
Not that kind of game. With bars like Emporium, Headquarters Beercade, Replay, and Logan Arcade sprinkled around Chicago, you never have to play video games alone on your couch again -- unless that’s your preference. If video games aren’t your thing, try a night of fancy darts at Point and Feather or Flight Club, or table tennis at Spin or AceBounce.

The Drifter Bar Chicago
Courtesy of The Drifter Bar Chicago

Steal away in a Speakeasy

It’s late, you want a drink and feel like being covert for whatever reason. Slide into a speakeasy like Watershed in River North (below Pops for Champagne), Hyde Park’s The Hyde, or the famed Violet Hour in Wicker Park. It doesn’t have to be a secret to be satisfying.

Dally at a diner

Honestly, I don’t know why I’m not at a diner more often. Open late or around-the-clock, the right diner provides comfort, prime people-watching and a touch of nostalgia along with a hot dish. Think loaded skillets and hot hashbrowns from Hollywood Grill, scrumptious vegetarian meals at The Chicago Diner, or sandwiches and shenanigans at White Palace Grill. It’s impossible to leave a diner without a story or two for the road.

Hit a happy hour you can actually get to in time

Barton G.
The freaks come out at night and do not get to work early enough the next day to make it to happy hour at 3pm, sorry. The over-the-top food and drink at Barton G. was made for Insta photo ops, and the restaurant’s Barton After Dark happy hour was made for those of us who like to sleep in. With specials at 9-11pm Sunday-Thursday and 10pm-midnight Friday and Saturday, the elusive happy hour pricing is in reach. 

Take a detour along the lakefront

Lake Shore Drive
Provided you’ve got a car and some gas, a drive up or down Lake Shore Drive is a quintessential Chicago experience. No matter your mood, views of the colorful skyline glittering at night are sure to improve your state of mind. No car? A walk, bike, or scooter ride on the Lakefront Trail with a backing track of waves splashing on the beach will get the job done just as well.

Sally Marvel Vaudeville
Ethan Jollie

See a draw-dropping vaudeville show

Bordel Chicago
There are fewer than 200 “verified sword swallowers” in the world, and one of them lives in Chicago. Catch Sally Marvel every Thursday night at Bordel as part of Vaudeville, “a weekly theater of sensational burlesque, strong magic, and unique sideshow acts.” While Marvel can swallow a sword and make a joke while doing so, it’s best to limit audience participation to swallowing cocktails.

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Liv Lawson is a Chicago-based writer.