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18 Things To Do In Chicago That Your Teens Will Love

Chicago is a vibrant city with something for everyone, including teens. With a fascinating past, a modern vibe, and plenty of fun activities, the Windy City has loads of things to do that your teen will love! Here are 18 awesome things to do in Chicago with teens.

Feb 28, 202316 min read

Anecia Ascalon
Anecia Ascalon
Team Building Expert

Chicago is a vibrant, bustling city with something for everyone. With a fascinating past, a modern vibe, and plenty of fun activities, the Windy City certainly has things to do that your teen will love!

Here are 18 awesome things to do with teens in Chicago!

1. Go Out On A Ledge At Skydeck

view from Skydeck

Teens who love an adrenaline rush will love visiting SkyDeck atop the Willis Tower. Formerly known as the Sears Tower, the Willis Tower is 1,450 feet high with 110 floors, making it the third tallest building in the Western Hemisphere!

SkyDeck is on the 103rd floor and offers phenomenal views! One can see up to 50 miles and four states. SkyDeck is reached by high-speed elevators that ascend 1,600 feet per minute.

As if the elevator ride isn't thrilling enough, your teens can step out onto ‘The Ledge’. The Ledge is made up of four glass boxes that jut out 4.3 feet from Skydeck. From these boxes, your teens can peer down at the streets of Chicago from 103 stories above. This is by far one of the best things to do in Chicago with your teens and tweens.

2. Turn Your Teens Into Escape Artists

The Escape Game Chicago

Playing an escape game is an incredibly fun thing to do in Chicago with your teens. In escape games, your group is ‘trapped’ in uniquely-themed rooms and the only way out is to solve puzzles, riddles, and clues in under 60 minutes.

The Escape Game Chicago in Downtown Chicago has several rooms with wacky themes your teenagers will find amusing. Each escape room is expertly designed to fit the theme.

In Gold Rush, your group is trapped in a desolate ‘cabin in the woods’ complete with old-fashioned lanterns and even a mounted deer head.

Prison Break, one of the more difficult escape rooms, finds your crew ‘locked’ in two prison cells next to each other inside a 1950s-style prison. Working together while separated is no easy feat - but it can be solved with your family working together!

Escaping in time is great but so is not beating the clock since your family will have a blast trying to figure a way out! The Escape Room Chicago is one of the most exciting things to do with your teens!

Plus, it's open until midnight, making it an ideal nighttime activity in Chicago for your older teens who like to stay up late!

3. Get Messy With The Blue Man Group

Take your teens and tweens to see the Blue Man Group at the Briar Street Theater but make sure they aren't wearing their favorite outfits because things are going to get messy.

This one-of-a-kind performance features three bald blue men dressed in all black. If that isn't as weird enough, they don’t speak for the entire show. But they certainly do entertain! With their sight gags, amazing percussion playing, and paint splattering, the Blue Men provide a multi-sensory experience like no other.

If you want a front-row seat to the antics, be warned. You’ll be in the splatter zone. Fortunately, you’ll be given aprons! Blue Man Group is great for all ages, so get tickets if you are in Chicago with the whole family!

4. Be Spooked On A Chicago Ghost Tour

For teens who prefer the supernatural to sky-high experiences, Chicago has several excellent ghost tours. Chicago has a storied past, and with that comes a dark side.

On a ghost tour, your teenagers will visit sights and hear spine-tingling tales about the hundreds of lost souls lingering around Chicago.

Try the Original Chicago Hauntings Ghost Tour, a 3-hour bus tour with stops at many of the city’s haunted locales and an inexpensive walking audio tour.

Are any of your teens true crime fans in your family? Try a 2-hour Chicago Gangster and Ghost Tours walking tour that combines mob stories and ghost stories. Hear about Al Capone and other grisly gangster crimes as well as the 1893 World’s Fair serial killer Dr. H.H. Holmes.

5. Make Some Waves

Choose from Lake Michigan and the Chicago River -- or both -- for some water time fun! For your active teens, a fun thing to do is to kayak on the Chicago River. Wateriders offers a history and architecture tour, a sunset paddle, a Navy Pier fireworks paddle, and a moonlight paddle.

Hop on City Cruise’s Seadog and get out on Lake Michigan. This jet-propelled boat ride reaches exhilarating speeds of up to 45 miles per hour. The fun doesn't end there. The Seadog takes you on 360-degree turns, sharp twists, and full-throttle slaloms.

With narration and music, the Seadog is sure to satisfy the speed demons in your group. Plus, it's an awesome way to cool of on a hot day in Chicago.

6. See World-Class Art

Art Institute of Chicago

The Art Institute of Chicago is a must-see for teens who are artistically inclined. The museum has a gigantic collection that includes everything from ancient art and objects to contemporary art. Works are from around the globe and span thousands of centuries.

The Art Institute houses the largest collection of Impressionist art outside the Louvre. Impressionist paintings are some of the easiest artworks for teens to relate to, as they contain everyday objects depicted in one of the most beautiful styles ever.

The museum offers workshops at their Ryan Learning Center where visitors of any age can stop by and create their own art to bring back home when their vacation is over.

TIP: On a rainy day in Chicago, the Art Institute, or any of Chicago's excellent museums, will keep your kids from complaining about getting wet!

7. Pose With The Bean

The Bean Chicago

If ever there was a great selfie shot for people of all ages, it’s posing with Cloudgate (aka “The Bean”). It’s one of the largest sculptures of its type in the world, measuring 66 feet long by 33 feet high and weighing 110 tons.

The elliptical sculpture by British artist Anish Kapoor, which was inspired by the element mercury, is made up of highly polished stainless steel plates. Chicago’s famous skyline reflects on its surface.

This iconic Chicago sculpture is located in Millennium Park, where there are plenty of things to do besides stand in front of a giant shiny bean!

There’s a calendar of events for the whole family. The Jay Pritzker Pavilion hosts concerts and other performances, some of which are free. In the winter there is an ice-skating rink.

8. Visit Chicago’s Riverwalk

Chicago Riverwalk

A gem of the Windy City, this 1.25-mile-long path along the Chicago River has so many things to offer the teens in your group.

Riverwalk is where you can find lots of architecture and sightseeing cruises, kayak tours, and boat rentals. See the options here.

There’s the super cool Art on theMART program, the largest permanent digital art projection in the world! Colorful contemporary artwork is projected onto the 2.5-acre riverside façade of the MART, the world's largest commercial building. This is absolutely Instagram-worthy!

Stop off at Sweet Home Gelato for creative flavors like Caramel Macchiato, Nutella Crunch, Bubblegum, S’mores, and Birthday Cake.

Riverwalk is a lovely place for a stroll after dark, so if you can leave the kids at home, come here for a romantic night out in Chicago.

9. Dig Into Chicago’s Famous Foods

Deep dish pizza

Chicago is famous for its deep-dish pizza. The best deep-dish pizza joints in town are Lou Malnati’s and Giordano's.

Lou Malnati’s is believed to be the first family name of deep-dish pizza. Lou got his talent by working at the first Chicago deep-dish pizzeria, which opened in the 1940s. Lou Malnati’s opened in the 1970s and since then they've been serving up some of the best hand-made deep-dish pizza in the city.

Some people argue that Giordano’s is the best deep-dish pizza in town. Their pizza is even more of a treat as it is double stuffed! The recipe comes from the family’s ancestors in Torino, Italy.

The first Chicago location opened in 1974. They now have locations all over the country and over a dozen in Chicago. Wherever you try Giordano’s your teens will be more than happy!

10. Discover Chicago’s Amazing Street Art

Street art and large-scale murals are much more than elevated graffiti. Street art is a globally recognized and compelling form of art. With modern themes, political messages, and bright colors, Chicago’s street murals will capture your teen’s imagination.

There are a few ways to see the city’s amazing street art. The easiest is to do the free Loop Mural Walk located in the Chicago Loop, the city’s official downtown. You can use this free, self-guided mural walk on your smartphone.

There are also street art tours which might be a better experience for your teen to learn the context and meaning of the murals as well as the skills used to make such grand-scale artwork.

Check out the Offbeat Street Art Tour or the Chicago Street Art Tour by Native 312.

11. Get Moving In Maggie Daley Park

Maggie Daley Park

Head to Chicago’s wonderfully designed Maggie Daley Park where there are lots of things for your teens to see and do.

Whether your teens are new to rollerblading or old pros, Maggie Daley Park is a cool place to blade! The Skating Ribbon snakes its way through the playful park landscape with views of the city. Rentals are available.

If you are in Chicago in the winter, the Skating Ribbon is transformed into an ice-skating track.

The park also has a large climbing wall divided into sections, one for beginners and one for advanced climbers. For a chilled activity, you and your teen can play on an 18-hole miniature golf course.

12. Get Creeped Out At The Medieval Torture Museum

Despite the museum’s ominous name, it isn't as scary as one might think. It is not, however, for the squeamish and is not recommended to those younger than 18 years of age. The Medieval Torture Museum is the largest interactive historical museum in the United States.

Over 100 medieval torture devices are on display, though not merely behind glass. The museum gives visitors an up-close look at the cruel torture implements with diorama-like set-ups using silicone dummies arranged to demonstrate how these gruesome devices were used.

There are a few opportunities for guests to try out a few of the devices, should they want to. For example, they can work the lever that dunks a victim into a vat of water - a torture technique used in witch trials.

The museum went to great lengths to create historically accurate exhibits to present a realistic atmosphere of the Middle Ages and many reviewers say that it is actually quite informative and interesting.

This museum may be the perfect combination of a history lesson and a majorly creepy experience that some teens will love!

13. Watch A Sports Game

Wrigley Field Sign

Among the best things to do in Chicago with your teen is to see some of the best sports teams around. The famous Wrigley Field is home to the Chicago Cubs. You can also check out the Chicago Bulls at the United Center. If you are in need of an activity for a work party in Chicago, take the crew to see a sports event!

14. Catch Some Rays

Volleyball at beach

Chicago offers teens the chance to lay out on the sand and get a suntan, something that many teens relish.

There are two dozen free beaches along Lake Michigan that are open to the public in the summer. Some have activities so that your beach time is more than sunbathing.

At North Avenue Beach you can rent paddle boards, kayaks, and even jet skis! There are beach volleyball courts as well. Food stands and restrooms are available. The 31st Street Beach also has water sports equipment to rent.

15. Explore Chicago By Bike

Chicago has some beautiful bike paths and trails, with the one most easily reached being the Lakefront Bike Path. It stretches 18.5 miles from Ardmore Avenue on the north to 71 Street on the south. The path runs parallel to Lake Michigan offering a leisurely biking experience.

The path passes through several neighborhoods and you can rent bikes at a number of these. Rentals are available at North Avenue Beach, Oak Street Beach, and Navy Pier.

You can opt for Chicago’s bike-share program, Divvy, with over 580 docking stations in the city. You simply pick up a bike at a self-service docking station and return it to any station when you complete your ride.

To learn about the city as you pedal, consider a guided bike tour. Find out what companies offer bike tours here.

16. Look Into Infinity

The WNDR Museum started as a pop-up installation that traveled the country but has become so popular that it is now a permanent art experience. It’s a super fun thing for your teens to do in Chicago which is why they’ll take more selfies than you thought possible!

The 30,000-square-foot space houses different types of contemporary art installations that rotate to showcase different artists' work. While WNDR is an interesting space, the highlight is the Infinity Mirror Room created by Japanese artist Yayoi Kusama.

Kusama has created 22 infinity rooms - small rooms lined with mirrors that create the illusion of endlessly recurring spaces. Each of her rooms has a different motif, from polka dots to colorful chandelier lights and more.

These infinity rooms are located in various art spaces worldwide, including this one in Chicago. This room is entitled Let’s Survive Forever. The room is filled with reflective steel balls and a small, mirrored column that houses an even smaller infinity room.

Kusama’s infinity rooms are immensely popular with teens, and though you won't spend more than an hour at the museum, pictures of it will show up on your teen’s Instagram feed for a long time!

17. Shop ‘Til They Drop

Teen and parents at shopping mall

Magnificent Mile has some magnificent shopping! This is the best place to start your teen’s shopping adventure.

There's Water Tower Place with over 60 stores. Your tweens and tweens will find some of the most popular chain stores here, like Forever 21, Hollister, Ragstock, Free People, and more.

If it’s vintage clothes they seek, there are plenty of excellent shops along North Milwaukee Avenue by Wicker Park like Penelope’s and Crossroads Trading. You’ll also find Urban Outfitters there. A surefire bet for your teens!

18. Bite Into A Donut... Or Four

Three people holding donuts

In the past few years, donuts have become quite the competitive dessert! Chicago has dozens of donut shops - so how to choose? Of all the things to do in Chicago with teens, the Underground Donut Tour may just be the most delicious!

This 2-mile tour covers Downtown Chicago, parts of River North, and finishes near Magnificent Mile. Along the way, the tour stops at four of the best donut shops in the city. Chicago never tasted so good!

Find out about more things to do in Chicago here.

For suggestions on how to plan your time, check out our 2 day Chicago itinerary!