Teens can be a tough crowd. Just when you think you’ve finally come up with a family vacation destination they will love, you get that dreaded eye roll. Fear not! I’ve been there and survived the eye roll — and learned that vacations with teens are the way to cement those family bonds. Time together, away from home, opens up conversation opportunities.
And, just maybe, you won’t get an eye roll if you tell the teens you’re headed to the Windy City. It’s a fun, sophisticated city with something to entertain just about anyone.
I raised my kids here. This is our list of the best things to do in Chicago with teens, according to my kids.
There’s a reason Navy Pier is one of the Midwest’s largest tourist attractions: there is so much to do there, from carnival rides to Shakespeare plays. Plus, it’s the best spot to get an Instagram-worthy shot of Chicago’s gorgeous skyline.
Don’t miss a ride on the slow-moving giant Centennial Ferris wheel (especially at night). In the summer, speed-loving teens will demand a boat ride on the Seadog.
If you can, plan your summer visit for a Wednesday or Saturday to catch the fireworks show or visit on a Saturday during the Christmas season to see the winter fireworks show.
And plan plenty of time for strolling the Pier — outdoors in summer and indoors in winter — to explore the many shops and restaurants.
Read More: Kid-Friendly Chicago Hotels
Art on the Mart is a free 30-minute light show projected each night onto the 2.5-acre front facade of the Merchandise Mart, a building that is so big it had its own ZIP code until 2008.
The best spot for viewing the show is along the south side of the Chicago River. Showings happen nightly, but times change depending on the time of year. Check the website for hours during your planned visit.
See the artwork (look for the giant deer near the Merchandise Mart), party boats, and restaurants as you take a scenic stroll along the Chicago River and through the Loop (that’s what we locals call downtown Chicago).
The riverwalk also has some yummy restaurants and is the place to catch a boat ride on the Chicago River.
Grab your active teens, rent a Divvy bike and head to the gorgeous 18-mile-long paved paths on the Lakefront Trail.
You’ll see the Chicago skyline on one side and Lake Michigan on the other. Stroll past the beach volleyball players at North Avenue Beach and visit the dog beach at Montrose Avenue.
Then head south to ogle my favorite attraction in Chicago — Buckingham Fountain — and the Museum Campus. That’s where you’ll find the Adler Planetarium, the Field Museum and the Shedd Aquarium. Just a little farther south is Soldier Field, home of our hapless Chicago Bears football team.
SheBuysTravel Tip: The bike path gets very crowded on the weekends. The best time to ride is early in the morning.
If you visit Chicago and don’t come home with a selfie taken at The Bean, did you really visit the Windy City at all? That means a trip to Millennium Park, Chicago’s answer to NYC’s Central Park.
The Bean is the centerpiece of the park. It’s a bean-shaped contemporary art sculpture with a mirrored surface. Snap a selfie with you in the middle surrounded by the city’s skyline. Officially, the sculpture’s name is “Cloud Gate.” But if you call it that, everyone will know you’re not a local!
Next to The Bean is the Crown Fountain, where two towers feature videos of people’s faces with water spewing from their mouths. On a hot summer day, you’ll find everyone from little kids to office workers cooling their feet in the water.
If you’re visiting in the summer, chances are good there will be a free concert, film or event at the beautiful Pritzker Pavillion on the day you visit. Check the schedule here.
Chicago is a city of neighborhoods. Each has its own character, art, and cuisine. Here are three of my family’s favorites, all easily reachable from downtown via Chicago’s easy-to-use elevated train system:
Pilsen: Located a quick Pink Line El ride from downtown, Pilsen is the place to find yummy local Mexican food, explore the giant murals painted on walls, and visit the National Museum of Mexican Art.
Chinatown: Just a few stops on the Green Line from downtown, Chinatown is lined with great Chinese restaurants and the stores where I buy my favorite Oolong tea for a fraction of the cost of buying it in a grocery store. Visit in February for the Chinese New Year’s festivities. Just be sure to dress warmly!
Wrigleyville: This is a can’t-miss spot in the summer when our beloved Chicago Cubs are in town. Take the Red Line from downtown to the Addison stop, right next to Wrigley Field, home of the Cubs.
Chicago is filled with world-class museums. These are the most teen-friendly:
Museum of Science and Industry: My lifelong favorite museum, you don’t have to be a science geek to find something fascinating here. It’s a bit of a trip to visit this museum in the Hyde Park neighborhood —you’ll want to take a rideshare if you don’t have a car.
The Field Museum: Home of Sue the T-rex, this one has never been at the top of my list, but it’s the museum my husband loves the most.
The Adler Planetarium: Part of the city’s Museum Campus along the lakefront, the planetarium is a fun spot to explore the history — and the future — of the universe.
DuSable Museum of African-American History: The nation’s oldest independent African-American museum, the DuSable is named for Jean-Baptiste Pointe DuSable, the Haitian-born founder of Chicago.
While there are plenty of family-friendly hotels in Chicago, if you’ve got teens, you’ll want to stay at Hotel EMC2. Part of Marriott’s Autograph Collection, it’s the place where the kids can put in an order via Alexa and have it delivered by robot! The robots, named LEO and CLEO, serve all sorts of amenities — water, slippers, extra toiletries and more — to hotel guests upon request.
Trying to make summer travel less stressful? Check out these take-along toys kids will love.
