14 Best Things to Do For an Amazing Nightlife in Chicago

Since most of us aren’t early birds, we mostly thrive when the sun goes down, which can be a tab bit tricky to find entertainment or other fun activities that are recurring, safe, and thrilling. Like, sure we do love a good happy hour deal during the day, but it’s next to impossible to leave work as early as 3 pm, to go to a bar after a careful selection, only to realize later that time has almost run out, ruining all your plans. But, don’t fret! Night owls or not, there are loads of things to do in Chicago at night - be it watching midnight movies, catching a burlesque show, sleepovers at the museums, and more. It’s never-ending! 

Continue reading to explore the nightlife in Chicago to keep you entertained after dark, whenever you’re in Chicago:

1. Watch a Movie under the Stars

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The Chicago Park District is known for hosting several flicks during summer, in parks, all over the city, for over 19 years. Hence, this calls for that perfect date night or a family night. You could look for movie nights happening in your neighborhood parks or traverse into another neighborhood. You can watch an 80s movie you’ve never watched before or a recent blockbuster you’ve watched multiple times - watching movies here are free. So, you can watch multiple movies guilt-free, and only spend your precious dimes on candies and snacks.

Where: Citywide 

2. Escape Into the World of Escape Rooms

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Back in the days, going to all the haunted houses in October or watching horror movies were all the rave. But, seeking these thrills only would happen once a year, during Halloween, when instead, you can lock yourself in a fun, puzzling room any day or time of the year. Yes, karaoke nights and trivia games are fun, but if you want to work your brain, with a bit of brain workout and stress, it’s time to up your game, as Chicago is a city filled with a plethora of escape rooms to get stuck in for a few hours. 

Where: The Escape Room Chicago, PanIQ Escape Room Chicago, Room Escape Adventures 

3. Take a Walk of Art

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Every month of spring, summer, fall, and winter, the Chicago Art District hosts Gallery Night on second Fridays. There are over a dozen galleries that participate. So how far or long you travel is really up to you. You can stick to one gallery at a time checking out art from local artists while eating cheese or small snacks and drinking wine.

Where: Pilsen 

4. Check out Vaudeville Shows

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There are sword swallowers all over the world, but there are only less than 200 sword swallowers that are verified, and one of them lives right in the heart of Chicago. You can catch a glimpse of Sally Marvel’s act every Thursday night as part of Vaudeville, at Bordel. You can also enjoy several other fun shows like magic, burlesques, and other sideshow acts. Although Marvel is known for swallowing swords while cracking a joke or two, you can stick to swallowing cocktails instead. 

Where: Bordel Chicago 

5. Spend Time along the Lakefront

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This one’s sort of best suited if you have got a car and gas, to take you to Lake Shore Drive. This classic Chicago experience will elevate your state of mind no matter what mood you’re in by offering blissful views of the colorful skyline that shines at night. If you’ve got no car, take a walk, hitch a ride, or even book a cab to the Lakefront Trail and enjoy the beach waves. This works well, too!

Where: Lake Shore Drive, Lakefront Trail 

6. Grab Drinks During 'After Dark' Happy Hours

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It’s 3 pm and it’s happy hour time at your favorite bar, but you’re still at work. And by the time you’re done with work, even the happy hour is coming to a close. How many of us have been in this situation? We know… the struggle is real!

So, how about we say that you get to enjoy happy hours post 9 pm every day of the week? Sounds fun, right? Barton G is known for curating drinks and food that fit perfectly on all the Insta posts and stories. And the restaurant’s After Dark happy hours is best-suited for folks who love to sleep in, or even for those who don’t.

Where: Barton G
Happy Hours: Sun - Thu: 9:00pm - 11:00pm; Fri - Sat: 10:00pm - 00:00am

7. Grab a Late-night Meal at a Diner

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This is an option that’s often overlooked, because, well… it’s a diner. But, diners are open around-the-clock. And the right diner offers a great spot for people-watching, offers comfort, a tasty dish, and a feeling that you’re in one of those Hollywood movies. You get everything from hashbrowns, loaded skillets, sandwiches, and many other vegetarian meals, as well. 

Where: The Chicago Diner, Hollywood Grill, White Palace Grill 

8. Play Games at the Bar

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Play games… not with hearts, of course. There are several bars spread across Chicago that offer video games. And if you don’t like video games, you can enjoy playing darts, table tennis, foosball, pool, etc, all while chugging down your favorite drinks.

Where: Flight Club, AceBounce, Headquarters Beercade, Logan Arcade, Replay, Point and Feather 

9. Karaoke Nights in Chicago

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One of the bustling neighborhoods in the city, Chinatown, is a place that never sleeps. Most of the cafes, restaurants, and bars here are open until 4 am during the week and all day and night over the weekends. You’ll see many people grabbing a tasty cup of bubble tea or an ice-cream in the winters. If you’re not in the mood for neither, karaoke is the way to go. Most of the karaoke bars here are open until 2 am or 3 am. 

Where: Zero Degree Karaoke Bar and Club, Chi Cafe, Sakura Karaoke Bar 

10. Drag Shows, Dance Floor, or Both?

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If you’re a night owl, catching a drag show, or going on the dance floor while the DJ plays the beats will fit right up your alley. If you’re planning on dancing all night long, watching drag shows, or just a fun nightcap session, Berlin Nightclub is the perfect place for you. It opens at 8 pm on some nights and 10 pm on other nights. Be rest assured that the party doesn’t stop till 4 am or 5 am. 

Where: Berlin Nightclub 

11. Check Out New Artists or Musicians

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Yeah, listening to the same old songs can be boring. So, how about adding some fun twists? All you need to do is enter the lottery and purchase the tickets from Sofar Sounds. The day before the show, all will be revealed - the performance location, that is. You may end up at a fancy home, or a record shop, or a bar… the location is a surprise. Some shows organized have an option of ‘bring your own booze’, while the others have cash bars. That being said, this is a great way to discover new music and artists. 

Where: Citywide

12. Or Head to the Show with No Surprises

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If you don’t like surprises, and you’d rather go to a concert where you’d know the artist beforehand, then know that the city is filled with live concert venues.

Where: Byline Bank Aragon Ballroom, Pilsen’s Thalia Hall, Reggies, Subterranean 

13. Go Bar Hopping

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Chicago has plenty of bars, literally in every nook and corner, so you’ll be spoilt for choice here. You could wander around neighborhoods like Boystown, Lakeview, and Halsted Street for a brilliant nightcap session. 

Where: Boystown, Halsted Street, Lakeview 

14. Night at the Museums

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You may visit most of the museums in one night, or visit just one every other night. Because every major museum in the city has something or the other to offer, especially in their after-hour program at a certain time during the year. 

Where: Adler After Dark, Field Museum’s Dozin, The Shedd, Museum of Contemporary Art, Art Institute, Museum of Science and Industry 

Chicago offers endless activities for one to indulge in during dawn, but that doesn’t mean when dusk approaches, the city has nothing to offer. From bar hopping to dancing, from karaoke nights to game nights, nightlife in Chicago is most-definitely an unparalleled experience.

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