20+ Epic Things To Do In Chicago With Teens + Tweens

A family of four bikes along the Chicago Lakefront Trail.
Photo Courtesy: Choose Chicago

Sometimes teens and tweens can be hard to please. But not here – teens love exploring Chicago, Illinois! Whether they are budding architects, avid history buffs, or shop-til-they-drop teens, they will find endless opportunities for fun in Chicago. If you’re looking for fun things to do in Chicago with teens and tweens, you won’t be disappointed! From world-class museums and attractions to great shopping and dining, the Windy City has attractions that will keep them entertained (and off their phones!) the whole trip. Keep reading to discover our favorite 20+ Epic Things To Do In Chicago With Teens + Tweens!

Fun Things to Do in Chicago for Teens and Tweens

Chicago is filled with fun things to do as a family! From magnificent shopping opportunities to captivating theater productions, there is no shortage of itinerary suggestions for your upcoming Chicago family vacation. Here are a few to get you started!

Explore Chicago’s Vibrant Neighborhoods

A man walks past a colorful mural in the Pilsen neighborhood of Chicago.
Photo Courtesy: Enjoy Illinois

If you’re looking for an exciting place to take your teens and tweens, look no further than Chicago! This city is full of vibrant neighborhoods with tons of things to do. One example is Chinatown, which is home to a sizeable Chinese community, as well as many Asian restaurants and shops. Start by checking out Chinatown Square, a two-story outdoor mall. From there, check out the gift stores or sample the best dumplings at QXY. Before you leave the neighborhood, don’t forget to try bubble tea!

Families visiting Chicago with teens also can’t miss Pilsen and the 16th Street Murals. While walking through this Latino-influenced neighborhood, you’ll discover tons of street art, a hip vibe, and must-try restaurants.

Finally, for a German-inspired neighborhood experience, be sure to visit Lincoln Square.

Cheer on a Local Sports Team 

An aerial view of Wrigley Field in Chicago.
Photo Courtesy: Enjoy Illinois

Those headed to Chicago with a sports enthusiast in the family can’t miss an opportunity to catch a game! There’s nothing quite like experiencing the energy and excitement of a live game, and it’s a great way to bond with your tweens and teens. Because the city has teams in all the major sports, you can catch a game no matter the season. Undoubtedly, a family trip to Chicago would be incomplete without experiencing a thrilling sports match and cheering on the home team.

Here are some great sporting events to consider during your family trip to Chicago with teens:

Enjoy the View from Skydeck Chicago

Photo Courtesy: Choose Chicago

Skydeck Chicago is an excellent itinerary idea for any family visiting Chicago! Teens will certainly get a kick out of visiting the tallest building in the city. Here, take in spectacular views of the Chicago skyline from the observation deck.

A basic admission ticket gives you access to the Skydeck, The Ledge, and various glass floor balconies. Families will see some of Chicago’s most iconic landmarks from the observation areas, including Willis Tower and the John Hancock Center. Plus, on a clear day, you can even see all the way out to Lake Michigan! Those traveling with tweens will appreciate that kids under age 11 get a discount on admission (ages 3 and under are free).

Looking to go to multiple Chicago Attractions? Save money with CityPass Chicago here!

Go Shopping

Two people stroll along the Magnificent Mile while shopping.
Photo courtesy: Enjoy Illinois

Chicago offers so many fun places for teens and tweens, and is also a perfect shopping destination! Many families easily spend half a day (or more!) wandering through the stores along The Magnificent Mile. This world-famous stretch of Michigan Avenue is home to some of the city’s best shops, from high-end department stores and luxury boutiques to teen-favorite hot spots for trending fashion. This includes shops like Coach, Patagonia, Sephora Michigan Avenue, and much more. Take a break from shopping with a carriage ride downtown. 

Other great shopping destinations for tweens and teens in Chicago include State Street (which is full of department stores like Macy’s), Wicker Park (which has lots of vintage stores and independent boutiques), and Oak Street (where you’ll find luxury brands like Prada, Gucci, and Hermes). Shopping is one of the best Chicago family activities with teens.

See a Show at the Chicago Shakespeare Theater

Photo Courtesy: Chait Goli

There’s something special about live theater that just can’t be replicated anywhere else. If you’re looking for an exciting activity to do with your tweens and teens in Chicago, you should definitely consider checking out a show at the Chicago Shakespeare Theater. From classic works like Romeo and Juliet to more modern takes on familiar tales, there’s bound to be a production that your whole family will enjoy.

Often, there are family-friendly plays not related to Shakespeare as well, including a current iteration of The Beauty and The Beast. Who knows, you might even find yourself getting swept up in the drama yourself!

Chicago Museums for Teens and Tweens

Chicago is home to some world-renowned museums, many offering special programs and exhibits tailored specifically for teenagers! So, if you’re searching for things to do in Chicago with teens, look no further than these fantastic museums.

Field Museum 

The entrance to the Field Museum.
Photo Courtesy: Field Museum

Undoubtedly, the Field Museum is one of the best things to do in Chicago. Here, families can learn about various subjects across several exhibit halls. With something to please everyone, it is a fantastic addition to any Chicago itinerary with kids. Start with the Griffin Halls of Evolving Planet, featuring a variety of fossils, animated videos, and other interactive displays. Then, move through the other exhibits featuring interesting topics like the Hall of Birds, ancient Egypt, and the Grainger Hall of Gems.

Then, dinosaur lovers, young and old, flock to the Field Museum, one of the biggest dinosaur museums in the world! This natural history museum showcases a variety of dinosaur-related permanent and timed exhibits, including Maximo, the Titanosaur, and SUE, a 40-foot-long T-Rex!

Note: Every Wednesday in the winter, the museum also offers free admission to Illinois residents.

Purchase the Go City Chicago pass here for discounted admission to Chicago attractions!

The Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and largest museums in the world. Located downtown in Grant Park, its huge collection is home to modern artworks from around the globe, spanning from permanent exhibitions to rotating installations. In the permanent collection, families can see some iconic paintings like American Gothic, Nighthawks, and Sunday Afternoon on The Island Of La Grande Jatte. Or, explore the rotating collections to get a taste for different kinds of art, from contemporary photography to kabuki prints.

Every Friday and Saturday, families are invited to stop by the Artist’s Studio, where they can take advantage of supplies to create their own masterpieces to take home! Undoubtedly, this is one of the best things to do in Chicago with teens and tweens.

DuSable Museum of African American History

A woman and two children explore an exhibit at DuSable Museum of African American History.
Photo Courtesy: DuSable Museum of African American History

Chicago is a city rich in history and culture. The DuSable Museum of African American History is a great place to learn about and explore one important aspect of the city’s past. Founded in 1961, the museum is named for Jean Baptiste Point du Sable, the first recorded non-native settler of what would become Chicago.

The museum houses a wide variety of permanent and temporary exhibits that showcase the contributions of African Americans to the city, state, and country. This includes works by renowned artists such as Jacob Lawrence and Romare Bearden, as well as a wealth of historical artifacts and documents. Families can also take part in hands-on activities, like making art or trying out traditional African drums. As one of the best family things to do in Chicago, you’ll definitely want to add this museum to your itinerary.

American Writers Museum

American Writers Museum in Chicago is an excellent place for teens to explore and learn about the country’s literary heritage! As the museum’s name suggests, it’s devoted to American writers, past and present, and features lots of interactive exhibits that families will love. Teens can learn about the lives and works of some of America’s most famous writers, explore the country’s literary heritage, and discover how writing has shaped our nation. Then, they can even try some writing for themselves on a vintage typewriter! There are also frequent readings and other events featuring famous authors. 

Discover Chicago on a Hop-on, Hop-off Big Bus Tour!

Chicago Sports Museum

Chicago Sports Museum is a must-see for any sports fan visiting the city! Located on Chicago’s Magnificent Mile near the Water Tower Place Mall, the museum features interactive exhibits and historical artifacts that chronicle the rich sports history of Chicago.

From legendary teams and athletes to the greatest moments and unforgettable games, it tells the stories of the city’s sports culture like no other. At the sprawling, 23,000 square-foot space, tweens and teens can test their skills on the same basketball hoop Michael Jordan made his iconic shot in the 1998 NBA Finals, then compare their stats to other sports legends. An entire section is devoted to the city’s beloved Bears, featuring interactive games and displays about the team’s storied history.

Chicago History Museum

There’s no better place to learn about the history of Chicago than the Chicago History Museum. From the city’s beginnings as a small trading post to its transformation into a global metropolis, the museum tells the story of Chicago and its people in an engaging and exciting way. Located in Lincoln Park, the museum is perfect for teens and tweens who love history. It offers interactive exhibits and educational programs that will keep them engaged and learning during your trip.

Right now, there’s an exhibit exploring the summer of 1871, when Chicago experienced an unprecedented heat wave and lots of fires. There are also permanent exhibits exploring different aspects of Chicago’s history, like its transportation history.

More Museums in Chicago for Teens and Tweens

Four teens look at a piece of art in the National Museum for Mexican Art in Chicago.
Photo Courtesy: Choose Chicago

Chicago is a city rich in culture and history, and plenty of museums reflect this. Check out these museum suggestions for more things to do in Chicago with teens! 

  • The Chicago Architecture Center is a great place to learn about the city’s iconic skyline! Teens can take part in hands-on activities, listen to stories about famous buildings, and see scale models of some of the most famous structures in the world.
  • The National Museum of Mexican Art is a must-see for anyone interested in Latino culture. The museum features a wide variety of artwork, including paintings, sculptures, textiles, and more. There are also often family-friendly events and programs taking place here.

Outdoor Things to Do in Chicago with Teens and Tweens

Sometimes families need a break from the hustle and bustle of city life. In that case, take your tweens and teens to one of the best outdoor things to do in Chicago for families. From lovely botanical gardens to thrilling amusement parks, the hardest part will be deciding which of these Chicago family activities to do first! Keep reading for more epic things to do in Chicago with teens and tweens.

Chicago is also among the Best U.S. Cities For A Memorial Day Weekend Getaway With Kids

Stroll Through the Chicago Botanic Garden

Chicago Botanic Garden is certainly one of the best things to do in Chicago with teens! Located on the city’s northwest side, the garden features over 27 acres of beautiful plants and flowers, as well as a variety of informative exhibits.

Tweens and teens will love learning about different plant species, especially those with an interest in science and nature. Additionally, depending on the season of your visit, there are a variety of seasonal displays throughout the year. This includes a lovely Orchid Show and a Daffodil Show. Finally, there are several family-friendly, educational workshops you can enroll in if your teens are interested in learning more. Budding artists and botanists can even enroll in an art class during your Chicago family vacation!

Take a Day Trip to Six Flags Great America

Six Flags Great America will surely be a hit with teens and tweens while on vacation in Chicago. Located in nearby Gurnee (in northern Illinois), around two hours from Chicago, this thrilling amusement park guarantees an epic day of fun! Together, tackle the thrilling Dare Devil Drive, Giant Drop, or the Raging Bull. Families can also challenge one another with water guns at the Buccaneer Battle! Aside from rides, Six Flags Great America also offers families live performances. On-site restaurants and cafes are perfect for grabbing a bite to eat throughout the day with hungry thrill-seekers.

Navy Pier

Navy Pier lit up at night with the Chicago skyline in the distance.
Photo Courtesy: Navy Pier

Navy Pier is an iconic attraction in Chicago! Nestled along the shores of Lake Michigan, teens and tweens will love exploring the many shops, restaurants, and other exciting sights here. Families can also stroll along the pier on a nice sunny day and enjoy the views of the Centennial Wheel and the lake.

Tweens and teens will love taking a ride on the Centennial Wheel, a huge Ferris wheel with views of the Chicago skyline and Lake Michigan. They may also like the carousel, Funhouse Maze, and other seasonal games on the pier. Navy Pier is also a great place to kick off your exploration of Chicago with tweens and teens, either with Divvy Bikes or on a boat tour. Finally, sunny days can also be spent lounging on the Chicago beach

The Chicago Riverwalk

People meander the Riverwalk along the Chicago River on a sunny day.
Photo Courtesy: Choose Chicago

Need a spot to give tweens and teens a little freedom to roam? The Riverwalk tops the list! This stunning pedestrian pathway follows along the south bank of the Chicago River. Parents (and teens, too!) will appreciate the breathtaking views of the skyline, access to some of the city’s best attractions, and plenty of opportunities to search for fun food.

If you want to spend more time exploring this area, take a boat ride or rent a paddleboard to explore the waters together. Finally, when you’ve worked up an appetite, stop at one of the many restaurants along the Riverwalk for a delicious meal to go with spectacular views! 

Book a Chicago Riverboat Architecture Tour

A Chicago Riverboat Architecture Tour boat takes passengers down the river on a tour.
Photo Courtesy: Choose Chicago

If you’re looking for a unique and exciting way to explore Chicago with teens, then a riverboat architecture tour is the perfect activity! These tours offer breathtaking views of the city skyline, as well as up-close and personal views of some of Chicago’s most iconic buildings. As you cruise down the Chicago River, you’ll see attractions like the Willis Tower, Neo-Gothic Tribune Tower, and Art Deco Wrigley Building. You’ll also get great views of landmarks like the Navy Pier and Buckingham Fountain.

But best of all, you’ll learn all about the different architectural styles that make up the cityscape of Chicago! This is an excellent activity for tweens and teens (and adults, too!) who will appreciate seeing the city from a whole new perspective.

As one of the best family things to do in Chicago, Get Your Guide offers a Chicago River: 1.5-Hour Guided Architecture Cruise

Check Out the Morton Arboretum

A young child explore a park with a huge wooden troll at the Morton Arboretum.
Photo Courtesy: Sylvia Lin

Need a break from urban exploring? Outdoorsy teens and tweens will love meandering through Morton Arboretum. Less than an hour from downtown, it’s certainly a fun addition to any Chicago family vacation. Here, stroll peacefully through curated gardens to see colorful flora and fauna. Or, make it an extended adventure by exploring sixteen miles of trails for a scenic view.

Hungry families will find a bite to eat at the on-site Ginkgo Restaurant. Finally, there are also various special events throughout the year, including the Illumination Holiday Light display. 

Spend an Afternoon at Millennium Park 

People walk around the Cloud Gate statue at Millennium Park in Chicago.
Photo Courtesy: Millennium Park

If you’re looking for some of the best outdoor things to do in Chicago with teens and tweens, a visit to Millennium Park is a must! This iconic park is home to tons of family-friendly attractions, including one of Chicago’s most iconic landmarks, The Cloud Gate, aka “The Bean.” It was designed to reflect the city’s skyline in its stainless steel plates. For sure, this is a must-do photo opportunity for your family! Families can also get great shots in front of the Crown Fountain or by walking across the Frank Gehry-designed bridge. After taking in a few of the sights, let teens stretch their legs on their own, while you relax on a nearby bench. Or, plan to have a picnic together.

In the winter, the park even boasts a fun ice skating rink (with skate rentals)! Finally, since it is right in the heart of The Loop, you can get some fresh air between sightseeing.

Be Active at Maggie Daley Park

An aerial view of Maggie Daley Park in Chicago.
Photo Courtesy: Maggie Daley Park

Need a more active outdoor experience? At Maggie Daley Park, teens and their families can climb, skate, and more along the Chicago lakefront. Indeed, teens will love the challenge of scaling the outdoor rock climbing walls! With a max height of 40 feet, it will surely be an epic urban adventure to remember. Sections are also divided into beginner and advanced areas.

Alternatively, the Skating Ribbon is a fantastic spot for having some family fun. Here, families can don their rollerblades or hop on a scooter to race around together (Didn’t bring your own, no problem! Both are available for rent on-site.) Winter visitors are also in luck, as it gets transformed into a skating rink when temperatures drop.

Finally, families can also find an exciting, Chicago-themed mini-golf course at Maggie Daley Park too! No matter what you’re into, this park offers some of the best family things to do in Chicago!

Where to Eat in Chicago with Teens and Tweens

A hand uses a pizza serving utensil to pick up a slice of Chicago-style deep dish pizza from Lou Malnati's.
Photo Courtesy: Lou Malnati’s

After exploring the many fun things to do in Chicago with teens and tweens, it’s time to eat! Undoubtedly, the Windy City has many great restaurants for families. From pizza places to hot dog stands, there’s something to please every palate! Of course, don’t miss the chance to try Chicago-style deep-dish pizza. We recommend fan favorites like Giordanos, Gino’s East, and Lou Malnati’s. Alternatively, Chicago residents also love their Italian beef! If one of those sounds good to you, check out Portillo’s and Johnny’s Beef.

Then, don’t forget about Garrett’s Popcorn Shop – get in line and order the cheddar and caramel mix! It’s the perfect Chicago afternoon snack! Or, make a pit stop at JoJo’s Shake Bar for over-the-top, photo-worthly shakes!

Finally, Chicago Magic Lounge is a 16+ venue (with a legal guardian), and a fun place to catch dinner and a show together. Teens will love the mix of magical theater, retro lounge vibe, and small-plate dining. Certainly, this is one of the most unique things to do in Chicago with teens.

Where to Stay in Chicago with Teens and Tweens

Photo of the indoor Junior Olympic Swimming Pool at the The InterContinental Chicago Magnificent Mile, An IHG Hotel, one of the best family hotels in Chicago.
Photo Courtesy: The InterContinental Chicago Magnificent Mile

Now that you know what to do and where to eat, it’s time to decide on where to stay in Chicago with teens and tweens. Firstly, the Four Seasons Hotel Chicago offers luxury accommodations in the middle of all the action. Not to mention, gorgeous lake and skyline views in the center of the Magnificent Mile. Another option families love along the Magnificent Mile is InterContinental Chicago Magnificent Mile, which beautifully combines vibrant local history with contemporary style.

Then, showcasing stunning views of the Chicago River and Lake Michigan, Swissôtel Chicago offers European-inspired elegance in large rooms and suites, ideal for families with teens. Finally, for more suggestions, check out our list of the Best Family Hotels in Chicago

Click here to Stay at The Langham, Chicago, for an Exciting Chicago Vacation with Kids

Use Our Interactive Map to Explore More Hotels in Chicago with Teens and Tweens

Booking.com (function(d, sc, u) { var s = d.createElement(sc), p = d.getElementsByTagName(sc)[0]; s.type = ‘text/javascript’; s.async = true; s.src = u + ‘?v=’ + (+new Date()); p.parentNode.insertBefore(s,p); })(document, ‘script’, ‘//cf.bstatic.com/static/affiliate_base/js/flexiproduct.js’);

Use this interactive map of Chicago hotels for families to plan your next stay in the Windy City with teens! Regardless of where you choose to stay in Chicago with teens, we know you’re going to have a great time exploring the city together.

Happy Travels!

Four teens check out their reflection in the Bean, located in Chicago's Millennium Park.
Photo Courtesy: Choose Chicago

We hope you found this list of 20+ Epic Things To Do In Chicago With Teens + Tweens helpful in planning your upcoming family trip to Chicago. From architectural tours to spectacular museums, great foodie finds, and so much more, Chicago is an outstanding destination with tweens and teens. You may even escape a dreadful eye-roll or two (but no guarantees with those persnickety teens!). Enjoy your Chicago family vacation!

*Due to the COVID-19 pandemic, some of the attractions, accommodations, or things to do on this list may be closed. Please ensure availability before making your decision. 

*This post may contain affiliate links that may earn us a small commission, at no additional cost to you. Affiliate links in no way inform the hotels, sights, products, or other recommendations included in our articles. All opinions and recommendations expressed here are compiled from submissions submitted by the generous members of our Families Who Love To Travel community.


Popular Reads
Two girls stand smithing with sunglasses on in front of five American flags in Washington DC.
10+ Things To Do in Washington DC with Kids

Washington DC definitely boasts some of the best things to do with kids! Having lived here for 15+ years, now Read more

13 Exciting Things to Do in London with Kids

My family and I moved to London recently, and we’ve had plenty of time to explore the city. I love Read more

Tourists gathered while sightseeing in Lisbon on vacation
Our Lisbon Family Vacation

Families Love Travel contributor Dana Arnold shares details of her recent Lisbon family vacation, including her favorite activities and restaurants.

5 Exciting Things to Do in Hanauma Bay with Kids

Hanauma Bay is one of the best locations for snorkeling with kids in the United States. Located along the southeast Read more

Thanks for reading!

Love our content?

Stay in the know by subscribing to our weekly newsletter.

Immerse yourself in a world of limitless exploration by joining us on Instagram at families.love.travel.

Join our vibrant Facebook community, "Families Who Love to Travel," (where family travelers like you can ask for advice and share tips with other families!).

Plus, you can read our latest articles by following our Facebook page.

Shop for Family Travel Memorabilia on Shop Families Love Travel.

Latest Articles

Child hiking trail through Yellowstone National park.

How to Plan a Yellowstone National Park Family Vacation

Everyone knows that Yellowstone National Park makes for a classic family vacation. Strolling the boardwalks...

A family of five stands on a sandy beach on a sunny day in Turks and Caicos.

Best Beaches® Turks and Caicos Review By A UK Family

Beaches Turks and Caicos may not seem like a typical vacation destination for a UK...

Three children swimming in blue water in Cayman Islands.

All About the Cayman Islands With Kids: Important Information You Need to Know

If you’re traveling to the Cayman Islands with kids, there’s some important information you need...


Travel Gift Ideas

National Park With Kids

Family Travel Tips

A mom holds her infant son on an airplane.

Use These 10 Tips For Your Baby’s First Flight

Families Who Love To Travel contributor Meghan Oaks provides her 10 best tips for your...

A young boy plays with legos on his airplane tray table during a flight.

18 Exciting Travel Toys For Young Kids That Will Keep Them Entertained The Whole Trip

When you're planning a family vacation, it's important to pack travel toys that will keep...

crusing with baby

Tips for Cruising with a Baby

Cruising is a great option for families with babies who want to relax and not...


Families Love Travel Team

The Families Love Travel Team has a zest for life and an even bigger passion for globetrotting! Comprised of real-life travel professionals, we work hard behind the scenes to provide dynamic solutions for adventuring with children. Our enthusiastic team understands the challenges that often accompany traveling with kids and is committed to making Families Love Travel an inclusive space to convey these experiences.