Things to Do with Teens in Chicago: 24 Activities That Totally Pass the Vibe Check
Family trips are great, until the teens start side-eyeing every stop on the itinerary like it personally offended them.
Planning out things to do in Chicago with teens means walking the tightrope between cool and cringe, all while hoping for at least one group photo where no one is fake-smiling.
Let’s be honest: teens aren’t always the easiest travel buddies. But find the right mix of skyline thrills, snackable eats, and activities that don’t feel forced, and suddenly everyone’s having a blast (and maybe even admitting it out loud).
From sky-high views to neon-lit adventures, these are the things to do with teens in Chicago that’ll make your trip feel less like a family obligation and more like a highlight reel.
Ready to plan a day that skips the sighs and wins some genuine smiles? Keep reading for 24 activities that totally pass the vibe check!
See the Windy City, Snap the Views
Explore Millennium Park
No Chicago trip with teens is complete without a selfie in front of “The Bean” (officially Cloud Gate), especially since it doubles as a mirror and an instant vibe check.
The interactive Crown Fountain is another win—bonus points if someone times a photo just as the digital face spits water.
Teens will appreciate the open space to roam (read: escape their parents for five minutes) while still being in the heart of the city.
As one of the most iconic attractions in Chicago, Millennium Park delivers on both photo ops and people-watching potential.
Ride the Centennial Wheel at Navy Pier
The Centennial Wheel is a 200-foot-tall Ferris wheel that somehow manages to be both chill and thrilling—especially when you realize how far you can see across Lake Michigan on a clear day.
The gondolas are climate-controlled, so yes, even winter visits are fair game and surprisingly cozy.
After the ride, teens can check out the carnival games or grab snacks while parents sneak off for coffee with a view.
It’s a perfect first stop at Navy Pier, and one that makes everyone feel like they’re on vacation, because they are.
Stroll the Chicago Riverwalk
The Chicago Riverwalk is one of those rare spots that feels like an adventure and a break at the same time. Teens can grab a boba tea or a bite from a riverside vendor while wandering past sleek skyscrapers and street performers.
For families looking to slow down while still soaking in the city’s energy, this scenic stroll checks every box.
Think of it as low-effort, high-reward, and one of the most underrated things to do with teens in Chicago.
Tour Chicago by the “L” Train
Forget the Uber—riding the elevated “L” train through the city is like being in your own gritty indie film.
The Brown Line offers some of the best views as it winds through neighborhoods and past skyline showstoppers.
It’s fast, affordable, and gives teens that independent-city-vibe they didn’t know they craved. Plus, it’s a low-key way to hit multiple attractions in Chicago in one go without having to re-park 12 times.
Visit 360 CHICAGO Observation Deck
Located on the 94th floor of the John Hancock Center, 360 CHICAGO brings the wow factor with sweeping views of the skyline and Lake Michigan.
The optional TILT experience literally leans you out over the city, making it one of the most thrilling observation decks in Chicago.
Teens love the glass, the altitude, and the chance to post something that screams “I’m cooler than my cousin in Cleveland.”
The Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck is a top-tier way to kick off the trip with a bang.
Step onto The Ledge at Skydeck Chicago
Skydeck Chicago sits atop the Willis Tower, and The Ledge is its star: a glass box that extends over 1,300 feet in the air.
It’s one of those things to do in Chicago for teens that’s equal parts terrifying and totally worth it (and yes, they will post it immediately).
The elevator ride is quick, but the bragging rights last forever. Don’t be surprised if this ends up being one of their favorite moments of the trip, even if they pretended not to care on the way there.
Cruise the Architecture River Tours
There’s something undeniably cool about floating past 50+ architectural icons while a guide casually drops facts about the city’s past, drama, and design.
Whether you depart from Navy Pier, Michigan Ave, Wendella, First Lady, or go all-in with a Lake & River combo, these tours are a crowd-pleaser.
Teens can relax, snack, and get schooled on architecture without feeling like they’re in class. The views, the vibes, the breeze—it’s Chicago at its best.
Take the Chicago by Night River & Lakefront Cruise
The city lights reflecting off the water? Gorgeous. A relaxing boat ride after a packed day of exploring? Ideal.
This evening cruise glides along the Chicago River and onto Lake Michigan, offering golden hour views and nighttime skyline magic.
It’s one of the most picturesque ways to wrap up your day—and makes teens feel like they’re in a cinematic montage.
Hop on a Big Bus Chicago Tour
This is sightseeing without the sweat: hop on, hop off, take breaks, repeat. The open-top bus offers fresh air, skyline views, and narrated facts that somehow don’t feel like homework.
It’s a solid pick for a full day in the city, especially since Big Bus Chicago offers stops near all the biggest attractions. For teens, it’s a laid-back way to explore; for parents, it’s a logistical dream.
Play, Fly, and Feast Your Way Through Chicago
Attend a Chicago Sporting Event
Few cities love their teams as loudly as Chicago does. Whether you’re cheering for the Bulls, freezing through a Bears game, or grabbing popcorn at a summer Cubs matchup, the energy is electric from the first whistle to the last play.
Stadiums here are more than sports venues. In fact, they’re cultural touchstones with serious bragging rights.
It’s no wonder a live game tops every list of things to do in Chicago with teens who love action, noise, and a good slice of pizza.
Step into the Magical World of Glow Circus
The Glow Circus turns an ordinary night into a kaleidoscope of light and movement. Expect neon acrobatics, mesmerizing hoop acts, and a soundtrack that makes it impossible not to tap your foot.
Teens will be captivated by the sensory overload and Instagram-ready visuals. It’s weird, wonderful, and totally unlike anything else in Chicago.
Visit The Insect Asylum
Equal parts museum, workshop, and art lab, The Insect Asylum is one of those quirky spots teens don’t see coming, but end up loving.
You can explore taxidermy, marvel at beetle collections, and even join a workshop to make your own specimen (yes, really).
It’s hands-on, a little offbeat, and surprisingly educational in the best way. Perfect for families who love mixing science with a dash of “eww, cool!”
Explore Haz Cooperative Studios
Haz Cooperative Studios is where local talent meets teen curiosity. The space hosts live music, art markets, and community events that give young creatives something to connect with.
Don’t be surprised if your teens start shopping for vintage finds or talking about joining a local band after a visit. It’s Chicago’s indie heartbeat, and a solid reminder that art scenes aren’t just for adults.
Experience iFLY Indoor Skydiving
Whether you go to Lincoln Park, Naperville, or Rosemont, iFLY gives you the rush of free-falling—minus the plane and parachute.
Teens get suited up, step into a glass tunnel, and soar on a cushion of air with the help of expert instructors.
It’s equal parts thrilling and empowering, and the photos look like something out of an action movie. For families seeking memorable moments, this one literally lifts the trip to new heights.
Feast and Cheer at Medieval Times Dinner and Tournament
Swords, knights, and a four-course meal without utensils: the Medieval Times Dinner and Tournament is chaos in the best way!
Teens will love the pageantry and action, while parents can sit back and enjoy the nostalgia of cheering for a favorite knight.
The Andalusian stallions, jousts, and explosions of pyrotechnics keep everyone glued to their seats. It’s dinner theater turned all the way up!
Dive into True Crime with Chicago Crime Tours & Night Crime Tours
This is where history meets thrill in a way that’s pure Chicago. From Al Capone to John Dillinger, these tours take you through the city’s most infamous crime scenes with a mix of storytelling and eerie fun.
The nighttime version adds just enough goosebumps to keep things exciting—without being too much. Perfect for curious minds who like a side of drama with their sightseeing.
Ride and Dine with Bobby’s Bike Hike Tours
This is sightseeing with extra flavor, and no one’s stuck sitting still. Bobby’s Bike Hike offers guided tours that mix biking, food, and fun facts in a way that actually keeps teens engaged (and yes, full).
Each route weaves through different parts of the city, with stops for bites like deep-dish pizza, classic Chicago dogs, and even local brews for parents.
Options like the Lakefront Neighborhoods Bike Tour, the Ultimate City Bike Tour, and the Bikes, Bites & Brews Signature Dishes Tour give families flexibility based on time, vibe, and appetite.
It’s a great way to explore the city without navigating trains or hailing rides all day. For teens who love food, movement, and a little adventure, this one hits all the right notes.
Set Sail on a Dining Adventure
Chicago’s skyline is even more impressive when viewed from the water, especially with dinner and music in the mix.
The Odyssey Chicago River Premier Dinner Cruise offers a glass-enclosed setting perfect for photo ops.
Meanwhile, the Chicago Premier Dinner Cruise on Lake Michigan brings elegance and glittering views.
On the other hand, the Spirit of Chicago Lunch Cruise is a more relaxed option, pairing skyline sightseeing with comfort food classics.
They are easily among the most fun things to do in Chicago for young adults who want a night that feels grown-up but still easygoing.
Whether it’s lunch with a view or dinner under the stars, these cruises turn dining into a full-on event.
Raging Waves
Located about 45 minutes from Chicago, Raging Waves is Illinois’ largest water park—and a guaranteed hit for teens who crave non-stop thrills.
With 32 slides, a massive wave pool, and an updated 2025 AquaVision screen, it’s a full day of high-energy fun.
VIP cabanas, faster food service, and mobile wallet passes make it surprisingly parent-friendly, too.
It’s the ultimate cool-down day that proves summer in Chicago isn’t just about the city, it’s about making a splash!
Museums That Actually Keep Teens Interested
Marvel at the Museum of Science and Industry
This isn’t one of those “walk slowly and pretend you’re fascinated” museums—it’s hands-on, high-energy, and legitimately cool.
From creating indoor lightning storms to climbing aboard a real WWII submarine, the exhibits are built to wow and engage.
Teens can explore space, weather, and robotics without it ever feeling like school snuck into vacation. It’s no wonder the Griffin Museum of Science and Industry lands on every must-do list for families visiting Chicago.
Discover Art at the Art Institute of Chicago
Home to icons like “American Gothic” and “Nighthawks,” this museum blends old-school masterpieces with modern must-sees.
Teens can roam from Monet to Warhol in the same visit and maybe even find a new favorite artist along the way.
Plus, the modern wing and immersive exhibits offer lots of photo-worthy moments (translation: they’ll actually want to look around). For art lovers or anyone open to being surprised, this place delivers.
Walk Through History at the Chicago History Museum
Forget dusty timelines—this museum dives into the city’s past with style and storytelling. Teens can explore immersive exhibits on the Great Chicago Fire, the city’s music scene, and the roots of local neighborhoods.
It’s one of those places that connects history to real life, making the past feel personal and relevant. If your crew loves a good origin story, this is the place.
Engage with American Literature at the American Writers Museum
This museum proves writing isn’t just about old books and boring lectures—it’s about voices that shaped the country.
Teens can dive into interactive exhibits, discover writers they’ve read in school (or should), and even create their own mini-stories.
It’s colorful, creative, and compact enough to keep attention spans intact. And with free admission for locals on select days, it’s as budget-friendly as it is brainy.
Dare to Explore the Medieval Torture Museum
Not for the faint of heart—or younger teens—this Loop-based museum dives deep into the darker side of history.
Graphic, immersive, and honestly kind of terrifying, it showcases the instruments and methods used during the Middle Ages in chilling detail.
Older teens fascinated by horror, history, or true crime will be very into it (with parental discretion, of course). It’s not exactly uplifting, but it’s definitely unforgettable.
Ready to Plan the Ultimate Chicago Adventure?
Chicago doesn’t just win hearts; it keeps everyone entertained, especially when you find the right mix of culture, food, and fun!
From sky-high thrills to unexpected museum moments, there’s no shortage of things to do in Chicago with teens that feel both exciting and effortless.
The key is in the planning, and that’s where Tripster makes it easy to pull it all together. With vacation packages through Tripster, families can bundle Chicago attractions, shows, and hotels for one seamless, stress-free experience.
Whether you’re exploring by boat, bike, or bus, you’ll find adventures that fit every mood and budget. Get ready to make memories, score great deals, and experience the best things to do with teens in Chicago like a pro!
Chicago Teen-Friendly Activity FAQs
Is Chicago safe to visit with teens?
Yes, Chicago is safe in the main tourist areas like downtown, Navy Pier, and Millennium Park—just follow basic big-city precautions. Stick to well-trafficked areas, avoid late-night wandering, and use rideshares or public transit wisely.
How do we get around the city without renting a car?
Chicago has a solid public transportation system with CTA buses and the “L” train network covering most attractions. You can also use ride-shares, hop-on-hop-off buses, or walk between popular downtown spots.
What’s the best time of year to visit Chicago with teens?
Late spring through early fall is ideal, with warmer weather for outdoor adventures like boat cruises, bike tours, and riverwalk strolls. Winter has its charm too—think ice skating, holiday lights, and indoor museums—but pack layers.
Are Chicago’s museums good for teens, or just little kids?
Many museums—like the Museum of Science and Industry, the Art Institute, and the American Writers Museum—have immersive, teen-friendly exhibits. They’re designed to be interactive, thought-provoking, and far from boring.
Can I book everything in advance to avoid long lines?
Absolutely—most major attractions offer timed-entry or skip-the-line options, and booking through Tripster makes it easy to lock in discounted tickets ahead of time. It’s especially helpful during peak travel seasons or weekends.
Are there any budget-friendly options for families with teens?
Yes! Many top spots like Millennium Park, the Riverwalk, and Lincoln Park Zoo are free, and bundled vacation packages through Tripster help save on paid Chicago attractions, shows, and hotels.
What can we do in Chicago if it rains or snows?
Head to indoor hits like Skydeck, 360 CHICAGO, museums, or catch a show or improv performance. Shopping at Water Tower Place or visiting the Insect Asylum are also great rainy-day wins.
How long should we stay to cover all the must-dos with teens?
Plan for at least 3 to 4 full days to hit a mix of outdoor sights, indoor attractions, and food-focused stops. That gives enough time to explore without rushing through everything.
Where should we book everything for the best deals and convenience?
Use Tripster to book Chicago attractions, shows, and hotels all in one place—plus, you can customize your trip to fit your family’s vibe and budget. It saves time, money, and a lot of planning stress.
