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20 Fun Things to Do in Chicago at Night

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Fun things to do in Chicago at night, by travel blogger What The Fab

Just because the sun has gone down doesn’t mean it’s time to call it a day—that’s why I’ve rounded up this list of the 20 best things to do in Chicago at night.

From a romantic stroll along Navy Pier to dancing all night long at one of Chicago’s hottest nightclubs, there are all kinds of nighttime activities to enjoy throughout the city.

Pssst, heading to Chicago? Don’t miss these travel guides to help you plan your trip!

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Anytime I take a trip to Chicago, the city brings out my inner night owl and makes me want to get out and have some after-dark fun! 

Whether you’re looking for a laid-back nighttime activity or feel like partying it up, there are plenty of fun things to do in Chicago at night, so let’s jump into this list of my top 20 recommendations.

Planning a trip to the Windy City? Book my fav Chicago activities below through GetYourGuide

20 Fun Things to Do in Chicago at Night

1. Visit Willis Tower Skydeck

Willis Tower Skydeck isn’t just one of the best indoor activities in Chicago—it’s also an incredible experience when you visit at night.

Towering over the downtown Chicago skyline, this Illinois landmark is the third-tallest building in the country, so you know the views are amazing. 

Standing over 1,300 feet tall, the Willis Tower Skydeck is America’s highest observation deck and draws over 1.7 million visitors annually.

One of the most incredible features of the Skydeck is The Ledge. This glass box juts several feet out into the air to provide views of four states (Michigan, Wisconsin, Indiana, and Illinois) and the sparkling lights of downtown Chicago at night.

Purchase a Skip-the-Line ticket through GetYourGuide to head straight to the observation deck.

2. Embark on a Ghost Tour

If you love the idea of hunting for spirits at some of Chicago’s most haunted spots, then a ghost tour is the perfect nighttime activity for you.

Several ghost tour options in Chicago will take you to infamous landmarks throughout the city, where paranormal activity is said to be a common occurrence. 

This Gangsters and Ghosts tour, available through GetYourGuide, highlights some of Chicago’s dark history as you walk around the Chicago Loop district. 

Another good tour option available on GetYourGuide is Windy City Ghosts, which focuses on spooky locations in the Northside area of the city.

Fun things to do in Chicago at night, by travel blogger What The Fab

3. Take an Architecture River Cruise

Try taking an after-dark architecture river cruise for a fun and unique way to see Chicago’s most iconic and beautiful buildings. 

These river cruise tours will take you past some of the city’s famous landmarks like the John Hancock Center, Tribune Tower, Wrigley Building, and more. 

You’ll learn about Chicago’s local history and culture as your boat cruises down the Chicago River.

As a bonus, an evening architecture river cruise provides the perfect opportunity to watch the sunset and enjoy the city skyline transition from day to night.

4. See Buckingham Fountain

Paying a nighttime visit to Clarence F. Buckingham Memorial Fountain is a must-do for anyone exploring Chicago after dark. 

With its colorful lights and dazzling water shows, this iconic landmark has earned a reputation as one of Chicago’s top tourist destinations.

From May to mid-October, you can get the complete Buckingham Fountain experience by watching an evening show where music and lights accompany impressive displays of water shooting 150 feet up into the air.

Buckingham Fountain is one of the largest in the world, and the area surrounding it is the perfect location for a romantic stroll or a night out with friends.

The best indoor activities Chicago has, by travel blogger What The Fab

5. Head to the Art Institute of Chicago

The Art Institute of Chicago is an iconic spot both day and night, and you can enjoy the museum until 8:00 PM on Thursdays.  

Established in 1879, the Art Institute of Chicago is one of America’s oldest and largest art museums, containing a stunning collection of art from various countries throughout history.

The Chicago Art Institute has an impressive number of artwork and artifacts that reflect a range of periods, styles, and cultures. 

This museum is a must-see for any visitor to Chicago and an attraction you can return to time and again. 

Make the most of your visit with a Skip-the-Line ticket from GetYourGuide.

6. Get a 360-Degree View of Downtown

Enjoy remarkable downtown Chicago and Lake Michigan views from 94 stories up at 360 Chicago Observation Deck in the John Hancock Center. 

The Observation Deck has several interactive displays and exhibits that teach visitors about local Chicago history. 

For an unforgettable experience that will get your blood pumping, take a ride on 360 Chicago’s TILT ride, an enclosed moving platform that extends from the building and tilts at a 35° angle.

After conquering your fear of heights, you can relax with a cocktail or snack at CloudBar, located right next door.

Skip the line by purchasing a ticket in advance through GetYourGuide.

Fun things to do in Chicago at night, by travel blogger What The Fab

7. Indulge in a Late-Night Bite

Chicago has many delicious late-night eats, from Giordanos’ classic deep-dish pizza to tasty tacos at Big Star and mouthwatering burgers from Kuma’s Corner.

This city has over 20 Michelin-star restaurants, and several of them are open late into the night. 

If you prefer a casual dining experience, there’s always a great variety of food trucks serving delicious food throughout town. 

GetYourGuide has several guided food tour options highlighting the best Chicago eats, like this Taste of Chinatown tour, where you’ll spend an evening walking from one delicious restaurant to the next.

8. Explore Navy Pier

Navy Pier is one of those can’t-miss Chicago attractions, and visiting at night makes the experience all the more memorable.

This 3,300-foot-long pier is located right along beautiful Lake Michigan, making it the perfect spot for an evening stroll with friends or family.

From seasonal ice skating rinks to the Centennial Wheel and all kinds of yummy restaurants and fun shops, there’s something for everyone to enjoy at Navy Pier.

Fun things to do in Chicago at night, by travel blogger What The Fab

9. Spend a Night at the Museum

Chicago is full of world-class museums, and what better way to experience them than by attending an after-hours or even an overnight event?

The Museum of Contemporary Art offers private evening tours to learn about the background behind some of the museum’s most iconic artists and pieces.

Another option is the American Writers Museum which hosts monthly Get Lit happy hours that combine drinks, music, open mics, and book swaps. 

For a truly immersive experience that little ones will love, check out the Field Museum’s Dozin’ with the Dinos and the Shedd Aquarium’s Asleep with the Fishes overnight events.

10. Cheer On Your Favorite Sports Team

Chicago has a notoriously vibrant sports scene, and catching a game is one of the most classic things to do in Chicago at night.

Basketball fans can catch a Bulls game at the United Center—if baseball is your thing, head to Wrigley Field to cheer on the Cubs. 

Whatever your favorite sport is, there’s a game to fit the bill! Going to a Bulls or Blackhawks game would be on my list of fun Chicago winter date ideas since you’ll be nice and warm inside!

Fun things to do in Chicago at night, by travel blogger What The Fab

11. Watch a Show at Chicago Theatre

The Chicago Theatre is the place to be for a great night of entertainment, thanks to its captivating decor and top-of-the-line production value for theatrical shows and performances.

From comedy shows to live music, there’s always something fun and exciting happening at Chicago Theatre.

You can stop by to admire the grandeur of the theatre’s spacious lobby, exquisite staircase, and magnificent auditorium—plus, the iconic marquis lit up at night is the perfect place to snap some Insta pics! 

With its wealth of nearby dining and nightlife spots, the Chicago Theatre is the perfect destination for a fun evening out on the town.

12. Enjoy Tunes at a Jazz Bar

Chicago is known for its deep jazz roots, so enjoying some tunes at a local jazz bar is a great way to experience the city’s authentic nightlife scene. 

The Green Mill cocktail lounge is a classic speakeasy-style bar with live jazz music and a fun atmosphere that comes to life after dark. 

For something more modern, you can try one of the many other iconic jazz bars around the city, such as Andy’s Jazz Club or Blue Chicago.

13. Grab a Nightcap at a Rooftop Bar

To end your night of exploring Chicago on a high note, I recommend visiting one of the city’s lively rooftop bars.

A rooftop bar provides the perfect excuse to sip on a tasty cocktail while overlooking the twinkling city lights of downtown Chicago.

There are fantastic options all around town, including Cindy’s Rooftop, a stylish spot atop The Chicago Athletic Association Hotel that boasts views of Millennium Park. 

Another fun choice for a rooftop bar is Raised Bar Chicago, located at the Renaissance Chicago Downtown Hotel.

These rooftop bars get busy on the weekends, so set up a reservation in advance if you plan to go.

14. Catch a Musical Performance

One of the classiest things to do in Chicago at night is enjoy a musical performance by the Chicago Symphony Orchestra.

The Chicago Symphony Orchestra, founded in 1891, hosts a variety of classical and contemporary concerts at their home venue, the historic Symphony Center.

What better way to end your night in Chicago than with a live performance by one of the world’s greatest orchestras? 

Whether you prefer the classics, like Vivaldi and Tchaikovsky, or want to check out new and diverse music by living composers, you’re in for a treat when you visit Chicago’s Symphony Center.

Image via Art on the Mart

15. Be Amazed at Art on the Mart

Art on the Mart is an innovative way for global artists to present their works on a massive public platform.

This exhibition spans almost two city blocks and towers up to 25 stories high, making it the world’s largest permanent digital art projection.

Everyone from renowned local talent to internationally-celebrated artists has hosted exhibits on this giant public art display since it launched in 2018.

The best part is Art on the Mart’s captivating projections are located along Chicago’s Riverwalk jetty between Wells and Franklin Streets—we love a fun activity that doesn’t cost a dime!

16. Journey to Space at Adler Planetarium

Every Wednesday night, Adler Planetarium (the world’s first planetarium) keeps its doors open until 10:00 PM to welcome late-night visitors.

Families, couples, friends, coworkers, and more can enjoy exploring the exhibits, galleries, and shows at Adler Planetarium.

It’s hard to beat the experience of learning about space after dark when you can step outside and see the stars with your own eyes!

17. Stroll Along the Magnificent Mile

The Magnificent Mile is an all-in-one shopping, dining, and entertainment destination along Chicago’s iconic Michigan Avenue.

This mile-long stretch of road is one of the most famous streets in the city and features luxury boutiques, restaurants, bars, hotels, and more. 

Regardless of your style or budget preference, there’s always something fun to discover while strolling down the Magnificent Mile.

This area is excellent for people watching or taking in breathtaking views of the downtown skyline, especially at night.

18. Dance the Night Away

For a fun night out, it’s hard to beat dancing the night away at one of Chicago’s fabulous nightclubs.

The city nightlife has something for everyone, from old-school hip-hop to edgy EDM and funky Latin beats.

My favorite is The Underground, a stylish and star-studded hotspot with yummy cocktails and fun DJs that’ll get you on your feet.

Other spots include Smart Bar, a Chicago classic since the ‘80s, and Sound-Bar, a massive space with two levels, nine full-service bars, and an enormous 4,000-square-foot dance floor.

19. Sample Local Brews

One of the best ways to experience a city’s culture is through its local beers, and Chicago is home to some exceptional breweries.

I’m not always the biggest beer fan, but I love trying new ones when traveling.

Lagunitas Brewing Company is a favorite for delicious brews and live music, and I love the warehouse vibes of Old Irving Brewing Company.   

If you’d prefer someone else to plan your evening, hop on a Bikes, Bites, and Brews Hiking Tour

20. Take a Walk Along the Chicago Riverwalk

My last recommendation for fun things to do in Chicago at night is to walk along the beautiful Chicago Riverwalk

You’ll pass scenic parks, unique art installations, and charming cafes that line the edge of the Chicago River.

Turn this into a romantic Chicago night out by packing a blanket and a bottle of wine to enjoy a peaceful picnic under the stars.

Add a jacket to your packing list regardless of the time of year you’re headed to Chicago since the nights can get windy and chilly!

Don’t forget to save this list of the best things to do in Chicago at night before your next trip!

If you visit any of these spots, I’d love to see your Chicago photos, so tag me on Insta (@wtfab).

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Are there cool things to do in Chicago at night?

Yes, Chicago has a lot of fun and unique nighttime activities to offer.

Is Chicago safe at night?

Most areas of Chicago are safe if you stay aware of your surroundings and travel with a friend or group, if possible.

Is Chicago a fun place to vacation?

Chicago is an excellent place to vacation for couples, families, solo travelers, and everyone in between!

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