20 Captivating Things to Do in Chicago with a Teenager

It’s the time of the year! Don’t miss out on the summer lazing around in your bed, and start making a difference for your teens. Take them to a place they have never visited to claim the award for the best parents. Now all you need to do is plan the best getaway with your teenager. Has Chicago ever crossed your mind? But what to do with a teenager in Chicago?

Whether to reside or visit, Chicago is a promising place that offers unlimited activities and things to do. We’ll help you uncover the beauty of Chicago by our lists of what to do with a teenager in Chicago. Aside from their amazing local invented Chicago pizza, Chicago is the place for your teens to learn about the beauty of old American architecture, attractions, and of course foods. A good fit for the brave explorers.

1. Aiming for the Best Boys Outing? Head to Wrigley Field

What to do with a teenager in chicago

Should you take your teenager to a baseball game? Definitely! The major attraction of Chicago is the baseball game. Famously known as the center of baseball, Wrigley Field takes baseball games to a whole new level. Wrigley Field has been the site of classic footage of plenty of legendary baseball games, as well as a home of the legendary Chicago Cubs. 

Wrigley Field is also open for a non-game day, you can take your teens to see a concert of their favorite artist or take them on an exclusive tour of the day. It’s also an essential tradition to snap a picture of the famous ivy wall. Baseball season is in a swing, don’t miss out on the opportunity to sit and cheer for the team your teens root for.

2. See the beauty of Chicago at the Highest Vantage Point at 360 Chicago Observation Deck

What to do with a teenager in chicago

If you’re planning a special trip with your family, 360 Chicago Observation Deck is the best answer to level up the excitement. Enjoy the burning view of Chicago’s famous architecture and skylines along with the famous lake Michigan roaring above 1.000 feet. On a very clear, sunny day, four states are completely visible. 

In an hour-long excursion, on the 94th floor of the John Hancock building, a full remarkable moment is guaranteed for your teens. They can get to the condo to devour the vantage view of Chicago at all costs. Dare your teens to the exhilarating ride of TILT, a giant moving platform that tilts the daredevils. The parents can also enjoy a sneaky cocktail at Bar 94 when your teens aren’t looking. 

3. Discover Chicago’s Art, Food, and Architecture Through This 2-Hour Walking Tour

What to do with a teenager in chicago

Introducing you to the beautiful crossover of Chicago’s best gems; art, food, and architecture. Through this tour, your teens can see Chicago’s truest potential. This tour offers an exclusive opportunity for walking exploration during the day to Chicago’s hotspots alongside local guides to taste Chicago’s foods, arts, and the remaining vintage architecture, as well as the new ones. 

Stop to grab Chicago’s styled popcorn to accompany your teens throughout the walking tour. Locally made chocolate is also an interesting option for snacking. Take advantage of Chicago’s beauty on walks here

4. Have a taste of the exhilarating ride of Lake Michigan

What to do with a teenager in chicago

Come to sail with thrilling speed along Lake Michigan on the speed boat. With this ride, your teens can see the fatal view of the Chicago shoreline through different experiences. 

The roar of the 2000-horsepower engine will take your crew into the most exciting day of their lives. This extreme speedboat is worth it in this summer reverie. Get soaked in the water with teenagers here

5. Hop into the Chicago Urban Adventure Cruise

What to do with a teenager in chicago

Shall we begin with the most exciting attraction in Chicago? It’s the Shorelines of Chicago. Since the Cloud Gate is already too media core, why don’t you take your teens to explore the water? The Chicago river and Lake Michigan are mandatory visits to the city.  

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This whole experience is packed with scenic spots of the famous landmarks of Chicago, from Navy Pier to Marina City. Revealing a new perspective on one of the biggest cities in America to your teenage sailor. This boat is worth the commission. Book here

6. Visit the Magnificent Mile of Chicago

What to do with a teenager in chicago

Magnificent Mile is the most notable district located in the heart of Chicago where all the magic happens. It’s an exceptional local city that submerges 50 historical landmarks and sightseeing spots for all ages. A perfect escapade with your curious teenager. 

The Magnificent Mile has it all for you. From the blaring nightlife for adults to the spectacular skyline and iconic architecture 150 feet into the sky on the new Ferris Wheel at Navy Pier. The Magnificent Mile is magnificent in a very remarkable way. 

7. Visit the Grand Art Institute  of Chicago

What to do with a teenager in chicago

Living up to its legendary name, the Art Institute of Chicago is a vast museum with an incredible amount of artwork on display. Preserving masterpieces from all over the globe, this is an ideal place to visit, especially if your teens have a thing for artwork. It is guaranteed to be a house of the best art you can find anywhere. 

The institute is famous for its signature Modern Wigs, where your teens can partake in this 30 minutes exclusive experience. There are endless exhibits of stunning statues. There will be no greater gift to give than the knowledge of the arts to your teens. 

8. Try out the salivating Chicago Tour Pizza

What to do with a teenager in chicago

This tour warrants an incredible experience to see the personality of Chicago in a single slice of pizza. There’s no better place to find the most authentic Chicago Pizza other than Chicago itself. The dripping deep dish Chicago pizza is what awaits your entire family on this exclusive tour. 

This tour features 4 spots of the best Chicago restaurants in town. Nothing comes near as good as this delightful foodie adventure. Book a ticket and bring your teens to their life-changing culinary trip in Chicago. 

9. Take an Excruciating ride to Chicago’s Family Food and Bike Tour

What to do with a teenager in chicago

A way to your teen’s heart is through good food. This trip involves 4 hours of sightseeing of Chicago’s top attractions, displaying the renowned city with its aesthetic and cultural assets. This tour is also a little different from the other tours, this food tour is set on a bicycle. Your teens can have the freedom to pedal forward to witness Chicago’s best attractions on their own. 

This tour is accompanied by a professional tour guide to answer all of the questions about your teen’s growing interest in the city. The stunning skyscrapers of the city are the background of this tour. Worth every penny you spend here. 

10. Head Straight to the Famous Chicago Greeter

What to do with a teenager in chicago
Source Image: Chicago Greeter

Ringing a bell with the famous Chicago Bean, the Chicago Greeter is the green vista of Chicago’s best interests. The Chicago Greeter highlights the green space and outdoor magnificent design. You can also start a detour with your teens here to the library and cultural center. 

This service consists of locals assisting your whole crew during the visit, giving your teens a completely new insight into the city. This tour also enables your teens to come to the 25 neighborhoods around and get down with the locals. 


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11. Immerse Your Teens with the Otherworldly Experience of Arts at the Van Gogh Chicago. 

What to do with a teenager in chicago

Chicago offers endless options of fun places, however, Van Gogh’s installation artworks will teleport your inspiring teenager to a heavenly dimension. The Original Van Gogh Chicago is a place you can’t miss out. This lush exhibit will take your teens to the otherworldly through Van Gogh’s works. 

This Van Gogh exhibit is highly interactive, everyone gets to see the brushstrokes and details of Van Gogh’s creation up close. Its 500,000 cubic feet projection delivers the creative vision of Van Gogh’s legendary art to your teens. This venue opens an opportunity for the youngster to see art through moving images and image installations. It offers the installation of Van Gogh’s celebrated artworks like The Potato Eaters, Starry Night, and so much more. Book Here! 

12. Stop By at the Legendary Garfield Park Conservatory

What to do with a teenager in chicago

Garfield Park Conservatory is the impeccable choice if your teen is more on the introverted side, but also desires a stimulating trip. The Garfield Park Conservatory is acclaimed by its visitors as the most astonishing conservatory in the world. Not to mention, the visit costs you nothing, as it is free for everyone wanting to take a look. 

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This green patio is one of the largest park conservatories human civilization has ever created. The breathtaking charms of this place lie in the green reverie of plants and flowers under the glass. Housed on 12 acres of land, cold frames, and endless plants are grown in the center of the Park and space for your teens to enjoy and interact.

13. Devour the Best Chicago’s Delicacies at Girl and the Goat

What to do with a teenager in chicago
Source Image: Girl and the Goat

After all the great explorations outside, do your teens need to refuel their energy instantly? Then, Girl and the Goat is a must-visit place for you. This restaurant has been serving its delish dishes for years. Serving the best foods to inspire their customers. Their authentic craft beers have attracted every local and global adult. Have a sip and feel the bubbles dissolve. Don’t miss out on their signature wine for over 12 years with the unbeatable experience of serving the best food in town. 

The Girl and The Goat serves a variety of menus from vegetables, fish, to meat as their main superstar. Their loaves of bread are baked fresh every day to guarantee excellent quality. Aside from the spectacular food, your teens can see the prime attractions of the chefs passionately executing their dishes. The Girl and The Goat is open every week and ready to welcome you and your teens to this exclusive restaurant! 

14. Drive to the Chicago Cultural Center

What to do with a teenager in chicago
Source Image: Chicago Gov

The Chicago Cultural Center is home to stunning free public events, making it one of the most visited places in the stunning city. Entertain your teens with the lavish building that holds the history of a century being the first public library. Don’t forget, that music, dance, theater, films, lectures, art exhibitions, and family events are free for you!

If your teen falls in between the nerdy historian kid and the explorer, this place is a wonderful fit for them. Snap as many pictures as you can, and absorb the city’s history while you are here. Book a tour here

15. Stop by at The Crazy Navy Pier

What to do with a teenager in chicago

Navy Pier is Chicago’s best wonder, people gatherer, and a top attraction for tourists to visit. The windy breeze of the lake, the fabulous view of the city, and the vast emerald water are the main attractions of this expansive open venue that are going to hook your teens up. Situated at Lake Michigan, there are many fun things to do you can try here with your teens. 

You can hop onto the ride and play games at Centennial Wheel, which takes you and your teens above the ground with the Skyview, and unforgettable Ferris wheel rides, restaurants to chill and the park. Navy Pier has it all for your family! 

16. Enjoy the Blissful of the Aqua Tower

What to do with a teenager in chicago

The award-winning Aqua Tower is a sensational building located in the Lakeshore area. The perfect stop for your teens who want to enjoy the city’s blazing luxury and the grand building that surrounds it. The fluidity of the building is striking to the eye, the most outstanding achievement in architecture is available every day for your young adventurer.  

The glory of the building is worth the commission. However, the central business district is also busy with lavish restaurants, eye-catching architecture, fancy hotels, and shopping stores that are extremely instagramable. Make it an unforgettable trip with your teens at Aqua tower!

17. Escape Artistry in Chicago 

What to do with a teenager in chicago

Voted as the best escape room in Chicago, Escape Artistry calls for a visit with your teenager. Exposing your entire crew to exhilarating games and thrilling puzzle missions, this place is created by the local artist of Chicago. Six games have to be completed within 60 minutes of each selected mission, like the Railcar and the Dollhouse. 

Each mission is designed for different levels of visitors. If you’re at an intermediate level, we suggest you take the logic game of the Railcar with your teens. But if your little champion is up for the extreme, we suggest the Roaring Dan’s of Pirate Dungeon. Then, the tournament of champions is on.

18. Wander at the Field Museum

What to do with a teenager in chicago

The Field Museum is introduced as the best vantage point of Chicago. Introduce your teens to three interactive sections of Chigaco’s, such as the Field of Museum, Shedd Aquarium, and Adler Planetarium. So many things to do in one single spot. 

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In the Field of Museum, cultural exhibits are displayed daily. If your teens have an intense passion for dinosaurs, this is the perfect place to visit. It showcases the biggest fossils of the Titanosaurus, the biggest dinosaur ever to exist. Head straight to the Shedd Aquarium if your teens are aquamarine geeks and let them witness the mimicry of the coastal ecosystem. Or turn to the Adler Planetarium, where you can dive into the infinity of space with its mysterious planet exhibits.

19. Skydeck Chicago

What to do with a teenager in chicago

Skydeck Chicago won’t be a dull destination for your teens in their leisure moments. Head over to one of the tallest buildings in the city and stomp your feet to the 103rd floor. A welcome view is the stunning scenery of the city from up to 50 miles away. Here, your teens can also spot 5 other states with admiration up in the air closest to the sky. 

Your teens can spend time walking down through the glass clear floor to see the greatest view of the city from all directions. Don’t stagger, the safety of your teens is guaranteed. Skydeck is a favorable destination to spend your time with your teens, don’t hesitate! Check off your bucket list of Chicago’s best visits here

20. Shedd Aquarium

What to do with a teenager in chicago

Shedd Aquarium offers a variety of sea creatures, ranging from sea belugas, and colorful jellyfish, to the adorable sight of penguins, sharks, and many aquatic animals your teens can interact with. Located on the shore of Lake Michigan, the highlight of your visit with your teens here is the famous Wellington penguin. Shedd Aquarium’s exhibits will be a fun place to entertain and educate your teens about marine habitats! 

Shedd Aquarium will satisfy your teens’ questions about the underworld and any animals they can only imagine! Secure a visit to personally say hi to Annie or Diego the penguins. Make Shedd Aquarium your first choice and hop into your car! 

With these 20 lists of things to do, we have helped you sort things out. What to do with a teenager in Chicago is not hard to figure out anymore don’t hesitate to travel straight to Chicago, and make the best out of your summer with your family. 

Here are 4 questions to help you get closer to your teens during this spectacular trip: 


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