Inside: Fun Things To Do in Chicago with Teens.

There is one thing I know for sure about Chicago. You will NEVER be bored while visiting and that’s a fact. Chicago is packed full of fun adventures, wild entertainment, great sites to see, and tons of shopping.

We just got back from taking a family trip to the windy city our teens and honestly, the city was way more fun than I thought it would be.

Here’s some of the attractions we saw and things we did that are sure to please everyone in the family; whether they’re adventurers, explorers, artists, shoppers, or information junkies.

Check out our favorite things to do in Chicago with teens!

Fun Things To Do in Chicago With Teens

Activities Teens Will Love

Maggie Daley Park

Maggie Daley Park is a great place to go climbing, roller skating, and having a good time on the beachfront. Test your climbing skills on the outdoor rock walls, which range in difficulty from beginner to advanced and reach a maximum height of 40 feet.

Now, it’s time to hit the pavement on roller skates or a scooter (both available for rent). Then you should check out the Skating Ribbon, a path that winds through a surreal park.

Want something with less of a pounding pace to satisfy your adrenaline fix? You can play mini golf among replicas of the Willis Tower, the Wells Street Bridge, and a Picasso sculpture, among other well-known Chicago landmarks.

This is a fun option for when you arrive if you’re feeling the need to get energy out before eating dinner.

Color Factory Chicago

Family Outing to Color Factory Chicago

Color Factory

Run don’t walk to get your tickets to the Color Factory right now! This was by and large our favorite activity we did while in Chicago. I was super impressed with how well it was done and my teens had a blast in the mazes, ball pits, balloon room etc. Matt and I had so much fun as well!

Sometimes, just getting to play together as a family is the best way to spend a vacation.

Such a fun idea for teens to play in the windy city

Escape Rooms

Chi-town has escape rooms where you can save the White House, get away from a zombie, or go on a mission to Mars. Nothing beats the adrenaline rush of a race against time, whether you’re trying to escape a goldmine, evade capture, or prevent an art heist. We always love these and scheduling one for after dinner was a great way to spend a family evening together.

If you’re in Chicago, you should visit Escape Artistry, Fox in a Box, and The Escape Game Chicago.

Activities for Teenagers in Chicago

Blue Man Group

The Blue Man Group at the Briar Street Theater is a high-energy theatrical experience that is loved by people of all ages. This is my kids #1 favorite show of all time! We’ve seen it in Vegas and now here as well.

It’s an event that combines live entertainment, humor, choreography, and lots of blue paint. Also, those who choose front-row seating should prepare to get wet (don’t worry, ponchos will be provided). You can kill some time before seeing a show by browsing the unique stores and antique shops that line Belmont Avenue and Halsted Street.

Museum of Ice Cream Chicago

Teen travel activities fun museums

Museum Of Ice Cream

The Museum of Ice Cream was something I’d read about online and was really as sweet as I imagined. It’s similar to the Color Factory in concept except focused way more on the obvious sugar and ice cream. We ate a LOT OF ice cream. Haha! So keep this in mind with your timing and plans.

What To Do in Chicago with Teens

Trendy Shops in Lincoln Park

Check out the unique shops in Chicago, here were a few of my favorites:

  • Teens who are both hip and artistic should be familiar with Threadless. The hip tee boasts artwork by unsigned designers from Chicago and beyond.
  • Pop-up stores, like the one that operates out of the company’s West Loop headquarters, are a great way to find out about limited-time offers.
  • Alternatively, Lincoln Park’s Frankie’s on the Park is a hip boutique filled with on-trend pieces for young women. We spent an entire afternoon popping into all the cute shops in Lincoln Park and they even had a gaming store my teen son was very excited about if you have a kid interested in D&D things.

What To Do in Chicago with Teens

Chicago Riverwalk

Chicago’s riverwalk, which has won numerous awards, is much more than a simple path. It’s not only a lively waterfront, but also a park with a wide variety of activities for people to enjoy in the city’s fresh air. In order to enjoy the little more than a mile of walking path, sights, sounds, and public art, rent a Divvy bike and ride leisurely along it. We stayed right across the street from the Riverwalk & it was a fun place to get some air and people watch.

Urban Kayaks also offers tours and rentals if you’d rather see the sights from the water. We saw a kayak tour go by while we were enjoying the riverwalk and for sure plan to put that on our itinerary next time we make it to Chicago.

Visit the McCormick Bridgehouse & Chicago River Museum for a unique viewpoint and a glimpse into Chicago’s past. Also there are a bunch of cute beer gardens, restaurants etc just lining the walk.

Family Fun in Chicago

Visit the Navy Pier

The Centennial Wheel on Navy Pier is a recognizable landmark in the Windy City. The wheel rises nearly 200 feet into the air, and its enclosed gondolas make it possible to enjoy a ride regardless of the weather.

Wednesday and Saturday evenings, from Memorial Day to Labor Day, Navy Pier hosts the Aon Summer Fireworks. Seasonal Pier Park features attractions like the Pepsi Wave Swinger, a carousel, climbing walls, and the Light Tower Ride. we traveled in October, and it was still a lively and fun spot to enjoy. The teens did the mirror maze, the wheel and they have a great arcade as well. This area felt like there was something for everyone, which is always a win!

The IMAX Theater and the Chicago Shakespeare Theater at Navy Pier are also great to check out if they have shows playing when you’re in town.

Navy Pier with teens

View from speedboat on Lake Michigan

SeaDog Speed Boating

Lake Michigan is where you want to go for your next adrenaline rush. We did an evening ride on Seadog’s jet-propelled speed boat ride.

It was my son’s favorite thing of the whole trip!

The boat goes fast, turns a bunch and gives you such a pretty view of the waterfront. The photo above was taken from my boat – beautiful! I love an activity where my teens have fun and I get to enjoy water & a view.

Family Vacation Ideas

Things To Do in Chicago with Teens During the Summer

Summer Festivals

Chicagoans love to celebrate everything under the sun. At least once a month, there is something that draws a large crowd. Put these teen-friendly activities on your calendars now:

  • From June to September, you can catch the Summer Film Series at Pritzker Pavilion in Millennium Park. Feel free to bring a blanket and relax on the Great Lawn or sit at the pavilion. While watching movies on a state-of-the-art 40-foot LED screen, featuring both classics and new releases.
  • Tastes of Chicago Every July, Grant Park hosts the nation’s largest outdoor food festival. Over 70 restaurants will be offering samples at the festival. This city has a thriving food scene, from food trucks to five-star restaurants, showcasing the city’s diversity. Listen to both well-known and up-and-coming live bands.
  • Chicago Summer Dance brings together dancers of all ages and abilities every summer to learn new moves in the open air at Grant Park’s Spirit of Music Garden. Parents and teens alike can benefit from taking dance classes together.

Summer Travel for Teenagers

Iconic Windy City Teen Activities

SkyDeck At The Top of Willis Tower

We ventured out onto the Skydeck and WOW this was a rush in more ways than one. Ha!

Not only are you up a seriously high 103 stories towering above the city, but you are also on a quick 15 second time-stop to get your photo in before moving on. The history of Chicago displays were really interesting and took some extra time, but the actual deck time goes really quick…. I highly suggested having your pose in mind before you step up.

Skydeck teen photo fun

Even still, I suggest doing this if you love heights and want really fun iconic Chicago trip photos to keep and save.

Thrill rides chicago with teens

Just maybe close your eyes while your teen does her handstands with only glass between her and the ground 103 stories down below. Yikes!

One tip we used for this experience was to go early, to beat the crowds. It is in the same building as the Color Factory, so you can do both things in the morning and still have a whole day ahead of you.

Chicago street instagram photo ideas

Architecture Tours

The buildings in Chicago were easily the tallest and some of our favorite that we’ve ever seen. There are many spots to stop, look up & of course snap those great social media photos.

Schedule an architecture tour or just spend a couple hours with a walking map of the loop like we did and enjoy the sites on your own. We really loved walking around this city and watching the building soar above our heads.

MSI Museum U-505 Sub tour with family

MSI Museum

We spent a morning at the Museum of Science and Industry and it was awesome! They have many exhibits for smaller kids, so if you have various ages happening in your family this activity is great for that. There were a few specific exhibits set up that my teens (and us parents!) loved seeing. Here’s what not to miss for the big kids in your travel clan:

  • The U-505 Submarine. Learning the history of this, seeing it in person and getting to tour the inside was such a great experience.
  • The Space Center – We got to see an actual piece of the moon, part of a rocket that had been taken up and they were preparing to open the Dragon exhibit which my son thought was the best.
  • A technology in fashion exhibit that my daughter loved.
  • A flight simulator ride that was very cool, although a little nauseating to be fair.
  • And a mirror maze, which was harder to figure out than I expected. Haha! I may have gotten a little lost here.
  • They also had a traveling Pompeii exhibit!

One quick note on the MSI museum: Although it was a great day, many of the exhibits cost extra money to see. I thought in the end it was worth the extra cash and it goes to helping the museum, but if you weren’t prepared for this you might get all the way over there and then miss out on some of the better displays and experiences. Look into this ahead of time and note how much it will cost to really see everything.

Food Tour Chicago

Great Places To Eat In Chicago

Food Tours

If we were excited about anything in Chicago it was the FOOD! And can I tell you it did not disappoint. We enjoyed going on a food tour of the loop one day and trying all the traditional Chicago style food. The hot dogs from

Deep Dish Pizza

Obviously eating deep dish in Chicago is something everyone needs to do. We went to 2 places Gino’s East Downtown, which was good and Pequod’s in Lincoln Park which is my favorite by and large. I suggest trying a couple places and voting on your favorite as a family.

Fun dessert ideas to eat in Lincoln Park

Don’t Forget Dessert

We had the most fun dessert while in town which is always a winning activity to do with my teens. Visit the Nutella Cafe downtown for yummy food & they’ll personalize a bottle for you!

These ice cream bathtubs at Center Street Kitchen in Lincoln Park were a hit!

And for dessert that pairs well with a great cocktail and a very pretty view, snag an after dinner reservation at Cindy’s Rooftop and the whole family will be happy.

More Fun Travel Spots for Teenagers

If you like these fun things to do in Chicago with teens and you’re wanting to plan more awesome trips, then check out a few more of our favorite vacation spots.

  • Fun Things To Do in Los Angeles – Sticking with our traveling in California with teens theme, check out our favorite things to do in Los Angeles. From fun roller coasters, cool downtown areas, and exciting rides, there is no your teens will be bored of this trip.
  • Fun Things To Do in Las Vegas – There are a ton of cool things to do in Las Vegas with teens. Exciting tour options include everything a teenager wants to see and conquer including zip lines, roller coasters, navigating an ATV or dune buggy, and there are even options to take them to a shooting range.
  • Fun Things To Do in San Diego for TeensThere are tons of great activities for families visiting San Diego, CA with teenagers to enjoy. From fun outdoor adventures, educational (but still fun) museums, and so much more, your teens will have no problem unplugging for a bit to enjoy all the activities you have planned. So check out what we learned and how we kept our picky teens happy all vacation long!