13 Epic Chicago Adventures with Teens for Your Bucket List

Chicago is a city that knows how to impress—towering skyscrapers, deep-dish pizza, and an endless lineup of epic things to do. Whether your teen is an adrenaline junkie, a history buff (even if they won’t admit it), or just looking for the best Instagram-worthy spots, this city delivers. Walk out onto the glass ledge at Skydeck Chicago, kayak the Chicago River surrounded by iconic architecture, or hunt for the best street art in Wicker Park. From museums that don’t feel like homework to thrill rides on Navy Pier, here are 13 unforgettable Chicago adventures to add to your bucket list!

Best Things to Do With Teens in Chicago

Visiting Chicago with teens? Take in breathtaking views from Skydeck Chicago, test your problem-solving skills at Escape Game Chicago, or explore marine life at the Shedd Aquarium. Discover fascinating exhibits at the Field Museum, stroll along the Magnificent Mile, or enjoy deep-dish pizza at a local favorite. Whether you’re into adventure, science, or iconic attractions, Chicago has plenty to offer!

1. Soar Above the City at Skydeck Chicago

There’s nothing quite like stepping out onto The Ledge at Skydeck Chicago—a glass balcony suspended 1,353 feet above the ground. Located in the Willis Tower, it gives teens the ultimate city view and a solid adrenaline kick. We went late in the afternoon, and seeing the skyline stretch into four states at sunset was unforgettable. The feeling of standing in mid-air with only clear glass below is both thrilling and oddly peaceful.

If your teen is into photography or anything Instagram-worthy, this spot delivers. Be sure to check out the interactive exhibits before heading up; they cover Chicago’s architectural history in a quick, engaging way. I’d recommend booking tickets online to skip the long line, especially on weekends. For a less crowded experience, early mornings work great. It’s a short visit, but one that really sticks—especially for teens chasing unique city experiences.

2. Test Your Teen’s Wits at The Escape Game Chicago

If your teen loves puzzles and fast-paced challenges, The Escape Game Chicago is worth adding to your itinerary. It’s located on East Ontario Street in River North, just a short walk from Michigan Avenue. Each themed room drops you into a timed mission—ours was “Prison Break,” and the whole family got way too competitive. You’ve got one hour to solve clues and crack codes before time runs out.

The staff does a great job setting the scene and offering just enough hints to keep things fun. Rooms like “Gold Rush” or “Special Ops: Mysterious Market” are popular with teens and don’t require any prior escape room experience. Book ahead—slots go fast, especially on weekends. It’s a great group activity that gets everyone off their phones and thinking together. If your teen enjoys a good challenge, they’ll be all in for this one.

3. Explore Underwater Marvels at Shedd Aquarium

For teens who geek out over marine life or just want cool photo ops, Shedd Aquarium hits the mark. Situated in Chicago’s Museum Campus, it’s packed with exhibits ranging from the Caribbean Reef to the Abbott Oceanarium, where we saw beluga whales gliding just feet away. The Amazon Rising exhibit was a surprise favorite—watching anacondas and piranhas up close was wild.

Shedd also has rotating animal encounters and daily feedings, which make each visit feel a bit different. If your teen likes sharks, Wild Reef has some of the best viewing tanks around. We grabbed lunch at Soundings Café, which has a nice lakefront view and decent options beyond typical museum food.

To avoid crowds, go right at opening or later in the afternoon. It’s easy to spend a few hours here without even realizing it.

4. Uncover History at the Field Museum

The Field Museum is huge, so don’t try to see everything—especially if you’re visiting with teens. We focused on the major highlights, like SUE the T. rex and Máximo the Titanosaur, and that alone took up a good chunk of time. The museum sits next to Shedd Aquarium, making it easy to pair the two into one epic day on Museum Campus.

The ancient Egypt section really pulled my teen in with its mummies and hieroglyphics, and the Hall of Gems had more sparkle than expected. For Chicago locals, check the calendar for free admission days. Otherwise, tickets can add up, so it’s best to prioritize the exhibits your teen is most into. We spent about two hours here and didn’t feel rushed. If your teen is curious about science or ancient civilizations, this place makes learning feel like exploring.

5. Get Breathtaking City Views at Navy Pier’s Centennial Wheel

Navy Pier is more than a tourist spot—it’s a teen-friendly playground with one of the best views in the city. The highlight is the Centennial Wheel, which soars nearly 200 feet above Lake Michigan. We rode it right before sunset, and the city skyline looked unreal from up there. The enclosed gondolas are climate-controlled, so it’s a solid option no matter the season.

Beyond the wheel, Navy Pier has carnival rides, food stalls, and public art that keep teens entertained without a big agenda. You’ll also find live music in warmer months and fireworks shows on summer weekends. Grab a snack from Garrett Popcorn or a slice from Giordano’s and enjoy a walk along the pier. If your teen is into skyline selfies or just wants some open-air fun, this spot checks a lot of boxes.

6. Unleash Creativity at the Art Institute of Chicago

Not every teen is into art, but The Art Institute of Chicago has a way of pulling them in. It’s home to famous pieces like “American Gothic” and “Nighthawks,” but there are also entire rooms dedicated to modern art, ancient artifacts, and photography. We started in the Thorne Miniature Rooms, which had my teen weirdly fascinated by the level of detail in each display.

The museum is in Grant Park, right off Michigan Avenue, and Chicago residents under 18 get in free. There’s a helpful app that guides you through highlights based on interest, so you’re not wandering aimlessly. We took a break at the Museum Café, which had solid coffee and decent snacks. If you want a mix of cultural exposure and quiet indoor time, this is an easy win—especially if it’s too cold or hot outside.

7. Get Sporty at Wrigley Field

Even if your teen isn’t a huge baseball fan, a visit to Wrigley Field still feels like an authentic Chicago experience. This iconic ballpark is home to the Chicago Cubs, and the energy during a game is contagious. We went on a summer afternoon, and from the ivy-covered outfield to the seventh-inning stretch, it was more about the vibe than the score.

If there’s no game scheduled, stadium tours are a great alternative—they take you through the dugouts, press box, and out onto the field. Nearby Wrigleyville has lots of fun places to grab food before or after, including Smoke Daddy for BBQ and Jeni’s Splendid Ice Creams. Definitely buy tickets or tours ahead of time, as it gets busy even on weekdays. It’s a relaxed but memorable outing teens can appreciate, especially if it’s their first time in a historic ballpark.

8. Step Into a Real Submarine at the Museum of Science and Industry

The Museum of Science and Industry is a massive, hands-on science museum located in Hyde Park—and it’s anything but dull. The highlight for our crew was walking through the U-505 submarine, the only German U-boat in the U.S. Teens can step inside and see the cramped quarters where sailors once lived. It felt straight out of a movie set.

Beyond the submarine, the museum has tons of interactive exhibits, from tornados and avalanches in Science Storms to a simulated coal mine that dives deep—literally. There’s also a rotating schedule of live demos and temporary exhibits, so check online before you go.

We spent nearly half a day here and still didn’t see everything. If your teen likes tech, engineering, or just pushing buttons and pulling levers, they’ll be hooked within minutes.

9. Catch a Show at the Chicago Theatre

Step into the dazzling world of live entertainment at The Chicago Theatre. Known for its iconic marquee, this historic venue is a gateway to a variety of performances, from concerts to comedy shows.

When pondering what to do in Chicago, catching a show at the Chicago Theatre should be high on your list. The venue itself is a piece of art, with its elegant architecture and grand interior. For teens, it’s a chance to see their favorite artists or discover new ones in an iconic setting. Whether it’s a rock concert, a stand-up comedy act, or a theatrical performance, it promises an evening of top-notch entertainment.

Check the theatre’s schedule in advance and book tickets early, as popular shows tend to sell out quickly. Arrive a bit early to enjoy the ambience of the theatre and maybe even catch a glimpse of the famous auditorium. Don’t forget to take a photo under the iconic marquee – it’s a quintessential Chicago experience.

10. Stroll Through Millennium Park

Right in the heart of the city, Millennium Park is where teens can stretch their legs, snap pics, and take in a bit of everything. It’s home to Cloud Gate—aka “The Bean”—which makes a cool backdrop for photos no matter the season. We spent almost an hour here just people-watching and checking out the public art installations.

There’s plenty to do without a strict itinerary. Teens can splash around in the interactive Crown Fountain, walk through Lurie Garden, or relax at the open-air Jay Pritzker Pavilion if there’s a concert going on. Since it connects easily to Maggie Daley Park and the Art Institute of Chicago, you can make a half-day adventure of it. We grabbed coffee from Intelligentsia nearby and wandered without a plan—it’s that kind of place. Laid-back and iconic, it’s a great intro to downtown Chicago.

11. Ride the Waves on Lake Michigan

For a break from skyscrapers and city streets, hit the water. Lake Michigan is an underrated part of the Chicago teen experience, and there are plenty of ways to explore it. We booked a kayak tour with Urban Kayaks, and paddling past the skyline was way cooler than we expected.

You can also try paddleboarding, rent jet skis, or hop on a speedboat cruise with Seadog Tours if your teen wants something faster-paced. The views from the water give a whole new perspective of the city, especially on a clear day.

Rentals and tours often start at Navy Pier or along the Chicago Riverwalk, so it’s easy to combine with other plans. Just check the forecast and book ahead—slots fill fast on weekends. If your teen likes being active, this is one way to burn off some energy with a side of sightseeing.

12. Savor Flavors at Chicago’s Food Tours

Tasting your way through the city is a fun and relaxed way to explore, especially with a teen who’s into food. We joined a walking tour with Chicago Food Planet, which covered Wicker Park in about three hours and included tacos, empanadas, and dessert. It wasn’t just a snack crawl—our guide shared cool neighborhood history and pointed out some impressive murals along the way.

Many tours, like their Best in Chow or Chinatown Adventure, are designed to be teen-friendly and flexible for picky or adventurous eaters. You’ll walk 1–1.5 miles total, so it’s active without being tiring. Tours often start in the late morning and end just in time for you to relax with a full belly.

Make sure to wear good walking shoes and bring a water bottle. For teens who want to try Chicago classics beyond deep-dish pizza, this is a flavorful way to dig in.

13. Spy on Wildlife at Lincoln Park Zoo

Set inside a leafy urban park, Lincoln Park Zoo is free, easy to access, and surprisingly packed with things teens enjoy. We visited on a sunny afternoon and saw lions, penguins, and even a red panda—all without buying a ticket. It’s small enough to cover in a couple of hours but varied enough to keep it interesting.

The zoo has several interactive areas, including an outdoor Farm-in-the-Zoo and educational exhibits focused on conservation. Teens who like photography will appreciate the zoo’s gardens and natural light, especially around Nature Boardwalk with its skyline backdrop.

If you need a snack break, Café Brauer is nearby, or you can bring lunch and eat by the pond. It’s a good combo of nature and city in one low-pressure stop. We didn’t expect to stay long but ended up lingering until closing time.

Frequently Asked Questions About the Best Things to Do With Teens in Chicago

Got questions about navigating Chicago’s vibrant scene with your teens? Our FAQ section is packed with insights on the best Chicago activities for teenagers, ensuring your family adventure is both fun and hassle-free.

Is Chicago a kid-friendly city?

Absolutely! Chicago is a fantastic city for kids of all ages, including teenagers. With its blend of cultural institutions like museums and theaters, outdoor spaces like Millennium Park and Lincoln Park Zoo, and interactive experiences like The Escape Game and Navy Pier, there’s no shortage of engaging activities. The city’s diverse neighborhoods also offer unique experiences, from street art tours in Pilsen to exploring the historic Navy Pier.

Where do teenagers hang out in Chicago?

Teenagers in Chicago have a variety of cool spots to hang out. The Magnificent Mile is popular for shopping and dining. For those interested in music and art, neighborhoods like Wicker Park and Logan Square offer a hip vibe with lots of cafes and indie shops. During summer, beaches along Lake Michigan are hotspots for teens. And for a bit of fun, places like Millennium Park and Navy Pier are always buzzing with activities.

What are the best things to do with teenagers in Chicago?

The best things to do with teenagers in Chicago include visiting iconic attractions like the Skydeck at Willis Tower for breathtaking views, exploring the vast collections at the Art Institute of Chicago, and enjoying interactive experiences at the Museum of Science and Industry. Outdoor activities like kayaking on the Chicago River or biking along the Lakefront Trail also offer fun ways to see the city.

What’s the best thing to do with teenagers in Chicago during winter?

During winter, one of the best things to do with teenagers in Chicago is to visit the Millennium Park Ice Skating Rink. It’s a fun and festive activity that teens usually enjoy. Museums like the Field Museum and Shedd Aquarium offer great indoor alternatives. Also, checking out the Christkindlmarket, a traditional German Christmas market, can be a unique and enjoyable experience.

Are there any unique Chicago fun activities for families?

Chicago is full of unique fun activities for families. You can catch an improv show at The Second City, where comedy stars are born. Exploring the city’s diverse food scene, from deep-dish pizza to ethnic cuisines, is also a great way to spend time together. For a bit of adventure, try the architectural boat tours on the Chicago River, which offer both education and entertainment.

What are some educational yet fun activities in Chicago for teens?

For educational yet fun activities, Chicago offers plenty. The Adler Planetarium and the Field Museum are great for learning about astronomy and natural history. The Chicago History Museum provides insights into the city’s past. For a hands-on science experience, the Museum of Science and Industry is unbeatable. These places are a true Chicago gem, combining learning with interactive fun, making them perfect for curious teens.

What are things for 18 year olds to do in Chicago?

For 18 year olds, Chicago offers a variety of activities. They can enjoy the vibrant music scene at venues like the House of Blues or explore the city’s rich street art in neighborhoods like Logan Square. For those interested in theater, catching a show at the Chicago Theatre is a must. Additionally, 18 year olds can participate in the many festivals and events that the city hosts throughout the year.

Can teenagers visit Chicago’s nightlife spots?

While many of Chicago’s nightlife spots are for those 21 and over, there are still options for teenagers. Several music venues and concert halls, like the Aragon Ballroom, host all-ages shows. Teen-friendly comedy clubs like The Second City offer performances that cater to younger audiences. Additionally, some cafes and lounges in the city have a relaxed atmosphere suitable for teenagers, especially during early evening hours.

Final Thoughts on Exploring Chicago With Teens

Exploring Chicago with teenagers is an adventure filled with endless possibilities. From the towering heights of the Skydeck to the immersive experiences at the city’s world-class museums, there’s something to captivate every young heart. The best things to do with teenagers in Chicago blend education, fun, and unforgettable memories.

Whether it’s marveling at the city’s architectural wonders, enjoying a day at Millennium Park, or savoring the flavors of diverse cuisines, each moment spent in this vibrant city promises to be as enriching as it is exciting. Consider staying in Chicago to make the most of your time and immerse yourself in the beauty and energy of the city.