Tweens — the word literally means “in-between.” Generally, ranging from ages 9 to 12, tweens are growing out of being little kids and getting closer to their teenage years. It can be a lot to navigate, from changing bodies and friendships to rapidly evolving likes and dislikes.
For parents and families traveling with tweens, those changing interests can make planning a vacation especially tricky. They may be too old for a children’s museum, but not quite ready to spend an afternoon wandering through an art museum.
Thankfully, Chicago is a city that can meet them right in the middle.
Why Chicago Is A Great City For Tweens
Chicago is a city full of culture, spectacular food, stunning architecture and adventures of all sorts. From the lake to sports arenas, shopping to skyline views, and plenty of Instagram-worthy experiences, there’s enough variety to keep tweens interested — while giving adults plenty to enjoy, too.
If you’re looking for the best things to do in Chicago with tweens, you’ll find plenty of options that will keep the whole family entertained. Whether you are looking for a calm weekend or one full of thrills, Chicago has it all.
10 Best Things To Do In Chicago With Tweens
All of the photos below are from my niece Ella’s visits to see me in the city when she was little, as well as our first visit back since I moved, in summer 2026. She is 11 and true definition of a tween and she gives her approval on these recommendations too!
1. See the city with CityPASS – this bundled offering gives you access to the city’s top attractions, at a discounted rate, with only one purchase. Options include Griffin Museum of Science & Industry, Field Museum, Art Institute of Chicago, Shedd Aquarium, 360 CHICAGO Observation Deck and more. The CityPASS makes it so easy to see so many of Chicago’s best offerings.
_________________
Why tweens like it: There is a lot of variety with CityPASS.
Best for: Tweens and families who want to see a lot of the city’s top attractions, including some of the best museums they have to offer.
Adult tip: Be sure to book your entrance times for each of the attractions you choose in advance. This will ensure you have plenty of time to see and do everything on your CityPASS list.
Sarah’s Personal Recommendations: Shedd Aquarium is one of the most beautiful aquariums in the country. You will see marine life of all sizes, set against a backdrop of the Chicago skyline and Lake Michigan. Griffin Museum of Science & Industry is a hands-on science mecca. Interactive exhibits allow visitors of all ages to develop a deeper understanding of science, while having a lot of fun doing so. Walk through a miniature version of Chicago or a real-life submarine. If purchasing the CityPASS be sure to take the river cruise and visit an observation deck too.
2. Set sail on the First Lady to explore Chicago’s architecture – in a city known for its architecture there is no better way to experience it than from the Chicago River. As you take a scenic ride along the Chicago River, your guide will teach you about Chicago’s history as well as its most iconic buildings. The First Lady architecture tour is led by the Chicago Architecture Center, which is a great place to purchase your tickets and explore more about Chicago’s architecture before stepping aboard. You can also pick up an Activity Pack for kids and younger tweens here as well, which will keep them engaged throughout the whole ride. Honestly it’s fun for the adults in the group too!
_________________
Why tweens will like it: The architecture cruise isn’t just about history and buildings, it’s a chance to cruise along one of the most scenic rivers and snap countless pictures along the way. At the end of the tour, as you near Lake Michigan you will have a perfect Instagram-worthy shot of the Chicago skyline.
Best for: Everyone, because who doesn’t love a boat! Although may be more suitable for humans who can sit still or walk around safely on a moving boat – aka, might be harder to corral a toddler here.
Adult tip: Book a cruise that will start about an hour before sunset. You will get to see the architecture in its glory in broad daylight and also get to enjoy the sun setting over this gorgeous city.
Sarah’s Personal Recommendations: I have taken this cruise probably a dozen or more times over the years, and love it just as much, if not more each time. Because every guide is different, every tour will be a little different. It’s truly one of the best things you can do to fully embrace the beauty that is Chicago.
3. Step out onto the edge at The Ledge at Skydeck – rising 103 floors above the street, The Ledge and Skydeck are an iconic destination atop the Willis Tower. This 3-in-1 attraction first takes you through a fun museum about Chicago and its neighborhoods, with plenty of cool photo ops. You’ll then ride the elevator that whisks you to the 103rd floor, with stunning views of the entire city. If you’re feeling brave, you’ll then step onto The Ledge, a glass floor balcony that extends four feet out from the building.
_________________
Why tweens will like it: Not many people can say they’ve been 103 floors up. A tween will love being able to brag that they’ve stood 103 floors above Chicago! They will also love seeing the city from this viewpoint and all the epic photos they will get.
Best for: View seekers and thrill seekers. You don’t have to step onto The Ledge, so even if you just want to see the view, you’ll enjoy this experience. The museum is fun and super easy to explore.
Adult tip: Check the weather and try to book on a day with clear skies. You’ll get to see farther, maybe even to another state. The Ledge lines move quickly as the staff time each group. Be ready for a photo op, as they guide you where to stand and take your picture.
Sarah’s Personal Recommendation: Even if you have a fear of heights, you will want to see the views! Stand back farther from the windows if needed. Heck, you can even step on The Ledge with eyes closed and only open them to look up at the camera. I may or may not have had to do this myself!
4. Soar above the city at 360 Chicago – a city the size of Chicago is bound to have two fantastic observation decks. Thankfully Chicago’s observation decks sit on opposite ends of the city, so you get two unique viewpoints. 360 Chicago offers just that, a 360 degree view of the city! In the heart of the Magnificent Mile, this observation deck is close to the lake and gives you stunning coastline views both north and south.
_________________
Why tweens will like it: The stunning views are a great reason, but they’ll probably love the TILT experience even more. As you might have guessed, TILT literally tilts you out over the city for an entirely new vantage point. This one is not for the faint of heart – it’s an adrenaline thrill high in the sky.
Best for: View seekers and thrill seekers alike.
Adult tip: CloudBar serves beverages for all age groups, as well as snacks and offers amazing views. A great spot to relax following some Michigan Avenue shopping. There are other seated observation areas as well, making this a great destination to enjoy rather than rush through.
Sarah’s Personal Recommendation: I’d certainly recommend visiting during daylight hours to get a great view of the city. If you want to prolong your time high above the streets below, grab a drink at the Signature Room’s Lounge at the 95th.
5. Visit the Museum Campus – Chicago is a beautiful city year-round, but it really shines and comes to life in spring, summer and fall. The Museum Campus is where several of the city’s most well-known attractions can be found, including Shedd Aquarium, Adler Planetarium and Field Museum. It’s near Soldier Field and offers stunning skyline views, as well as plenty of beautiful nearby parks and places to relax along Lake Michigan.
_________________
Why tweens will like it: There is plenty to see and do here, and plenty of cool places to explore. Skyline views are excellent and another great spot for a photo op.
Best for: Truly good for all ages – small kids can run around, tweens can soak up all that the area has to offer, and adults can enjoy the views from a number of great resting spots.
Adult tip: Getting here by rideshare can be costly or tricky depending on the time of day. The 146 Museum Campus bus is the best bet and can be picked up from most areas on Michigan Avenue. You can tap a credit card to pay for bus fare onboard.
Sarah’s Personal Recommendation: Make this a day-long destination. Explore a museum or two, have lunch in a park, stroll along the lake and walk by Buckingham Fountain – which shoots water 120 feet in the air.
6. Spend time at Maggie Daley Park – when Maggie Daley Park opened in 2014, kids of all ages rejoiced. This 20 acre park offers a little bit of something for everyone. Water features, plenty of grass to lounge and run, an ice ribbon in winter, rock climbing in summer and some of the greatest playscapes a kid could imagine.
_________________
Why tweens will like it: It’s a great place to run and get out energy, with cool climbing features, and plenty to explore. They’ll also enjoy the walk across the giant silver bridge to Millennium Park, where they can see the famous Chicago Bean (aka Cloud Gate), Pritzker Pavilion and Crown Fountain, where giant faces spray water across the pool.
Best for: Any age group! There is play equipment here for babies to teens, and even adults who are kids at heart.
Adult tip: You might think you won’t need a lot of time at a park, but this one offers so much to see, so give yourself ample time to enjoy it. Enjoy the fact that a park where so much is free, can be just as exciting as the adventures that require a ticket and a cost.
Sarah’s Personal Recommendation: If you have kids who like to splash, bring a change of clothes because there are plenty of things here that might be considered the “splash zone.”
7. Take a bike ride along Lake Michigan – one of the greatest things about Chicago is the variety of ways to get around the city that aren’t quite traditional in most other towns. There’s the CTA which includes the EL (elevated train), subway, bus lines, plus rideshares and cabs and plenty of walking. But one of Chicago’s best features is the Chicago Lakefront Trail, an 18-mile path along Lake Michigan. Why walk it when you can bike it!
_________________
Why tweens will like it: It’s a fun and active way to explore the city. Let them lead and make choices on where you go and when you stop.
Best for: Best for tweens, teens and adults. While biking can be a lot of fun, the trail can get busy, so safety and bike-handling skills are a must.
Adult tip: Bring helmets from home and then rent Divvy bikes! You can pay for a day pass and unlock bikes across the city at your leisure. This allows you to ride anywhere you want (well, near a Divvy station – but the app will tell you that) and stop when you like, never having to worry about locking your own bikes or transporting them. Plus, if you ventured far and are tired at the end of the day, simply park your bike at a station and catch a ride home.
Sarah’s Personal Recommendation: Talk about safety and rules before anyone gets on a bike. The Lakefront Trail has clear lanes for bikers and walkers, and you should use them like you would a road. Teach tweens and teens the “rules of the road” before you ride to avoid any issues or injuries. Also good to teach them to call out “on your right,” or “on your left” as they pass people.
8. Get your sea legs at Navy Pier – this pier has become iconic to the city of Chicago, a landmark, if you will, for over 100 years. It has a storied history which makes it extra special. It was first a municipal pier, then housing for military during World War I and was a naval training base for the U.S. Navy during World War II. Nowadays it’s a whole lot of fun packed onto a 3,300-foot pier.
_________________
Why tweens will like it: There is ample activity on the pier for people of all ages. Boat rides and dinner cruises line the outside of the pier, while up top you can take a spin around the giant Ferris wheel, ride the historic carousel or go for a swirling swing-ride. The interior is lined with quick food options as well as sit-down restaurants. The newest addition to the pier, Flyover, will truly have you soaring.
Best for: Navy Pier truly offers something for any Chicago family vacation. They have activities year-round as well, so it’s not just a summer destination.
Adult tip: If your family has little ones in it too, the Chicago Children’s Museum is located on Navy Pier and is an interactive children’s paradise.
Sarah’s Personal Recommendation: Stroll along the entire pier, as the views get better as you go! The Ferris wheel is not cheap but it’s worth the Chicago views. If you have kids with you who love fountains, the one at the entrance makes for a great splash zone!
9. Eat your way across the city – while Chicago is known globally for a few special foods, like deep-dish pizza, Italian beef and Chicago-style hot dogs, it doesn’t always garner the foodie city badge that it should. Every neighborhood of the city is filled with incredible restaurants and unique foods. You truly have endless opportunities for your taste buds!
_________________
Why tweens will like it: No matter how picky your eater may be, there will be something they love in Chicago! Sure, there are plenty of great restaurants for the whole family, but some of the most tween-worthy spots include Hello Kitty Café, Nutella Café, the multi-story Starbucks Reserve on Michigan Avenue, JoJo’s Shake BAR for the most over-the-top milkshakes, American Girl for a delightful tea-style lunch (dolls included), Ed Debevic’s for an old-school diner where the staff won’t go easy on you and Harry Potter’s Butterbeer Bar.
Best for: Any living being, young, old and in between who enjoys food.
Adult tip: Find the food halls and let each member of the family pick what they want. It’s a fun way to enjoy a meal, plus everyone walks away with the cuisine their heart desires. There are many great food halls throughout the city, including Aster Hall (Bloomingdales mall), Urbanspace (Willis Tower) and Sterling Food Hall.
Sarah’s Personal Recommendation: I lived in Chicago for nearly 14 years and had the luxury of trying so many incredible food establishments. My favorites are Do-Rite Donuts (I dream about their gluten free chocolate Valhalla donut), Café Ba-Ba-Reeba! for the best tapas is in the city (be sure to get the bacon-wrapped dates and patatas bravas), Carnivale for an incredible atmosphere and authentic food and Rocks in Lakeview East – it’s a typical bar, but the grilled cheese is out of this world.
10. Go on a social media selfie-tour – tweens are growing up in a world of social media, YouTube and short-form video. Even if they don’t social media yet, they know about it and all the trends it sparks. One of the most fun ways you can explore the city with a tween is to set it up like a selfie tour. Have them find places that are the perfect backdrop for a selfie and snap away. At the end, make a video, I mean a reel, and if you desire, post it to social media.
_________________
Why tweens will like it: It’s a great way to keep them engaged throughout the trip and lets them be a kid and a tween all at the same time. It opens up their creativity and lets them find the perfect shot too. Maybe they love sports, so you go to Wrigley Field and the United Center. Maybe they love animals so you go to the Lincoln Park Zoo (which is free by the way). Or maybe they love shopping, so you document the best stores you visited. Whatever they decide, they will have fun with it.
Best for: Any kid who is obsessed with social media, likes photography or has even an ounce of creativity.
Adult tip: Let them do some research as you plan your Chicago family vacation and share places they want to visit to snap a viral photo. This will get them excited before the trip begins. Surprisingly this will get their heads up looking around, and out of their phones more often. Afterwards, you’ll have tons of visuals to remember your time in Chicago.
Sarah’s Personal Recommendation: Tag @sarahinstyle on Instagram if you do this! I’d love to see your selfie tours and share them. Also, set an example and put down the phones when you’re not capturing your selfies. Be in the moment and enjoy your time in Chicago and your tween will too.
Whether your tween loves adventure, food, photography, sports or simply exploring a new city, Chicago has plenty to keep them entertained. From the Skydeck and architecture cruises to Navy Pier and the Lakefront Trail, these things to do in Chicago with tweens can turn a family trip into a vacation everyone actually enjoys and will remember for years to come.
For more information on this wonderful city and all it has to offer visit ChooseChicago.com.
Planning a trip to Chicago with younger kids? I’ve got you covered! Check out a few of my other articles – Best Things to do with Kids in chicago and Best Winter Activities with Kids in Chicago.
Signed with Style,
