Once your kids hit middle school and high school, they're ready for more grown-up fun, including when the family is on vacation. There are many engaging activities to add to your to-do list when visiting Chicago, Illinois, with teenagers. The Windy City offers exciting adventures like witnessing sharks and rays being fed, catching breathtaking views from the Willis Tower's 103rd floor, watching a play or comedy at a local theater, or taking a segway tour of the city's historic architecture or around the lakefront. There are also parks and piers with great skyline views and plenty of interesting activities for everyone in the family.
The Willis Tower, the tallest building in the Western Hemisphere, features 110 stories and adventures for all ages. For a truly unique experience, head to the tower's 103rd floor Skydeck, where you can step into glass boxes on the Ledge, extending four feet beyond the edge of the building for a selfie dream come true and jaw-dropping views. It's the highest observation deck in the United States and is only a 5-minute walk from Union Station in central downtown.
The attraction also has interactive exhibits and family activities such as games, a theater presentation, scavenger hunts, and coloring pages.
Sightseeing is more fun for teens when they've got their own wheels. Absolutely Chicago Segway Tours will show you around the city from behind the handlebars of a Segway—a two-wheeled, self-balancing, battery-powered electric vehicle that's a blast to ride. There are a dozen tour options, including the Lakefront and Museum Campus, The History of Chicago Architecture, and Lincoln Park/Gold Coast. Children must be at least 12, and any riders under age 18 need to have an adult with them.
Teens like excitement, and the Shedd Aquarium brings it with a premium experience: the behind the scenes Wild Reef Shark Feeding Tour. You'll not only have a chance to watch sharks and rays eat but be up close to corals and sea stars. Enjoy the 400,000-gallon shark habitat while learning about the creatures’ role in their ecosystem. Attendees ages 10-17 must be accompanied by an adult.
Chicago has a vibrant theater scene with over 200 venues ranging from storefront, low-budget theaters to major cultural centers with multi-million dollar shows. There is truly something for everyone in your group. Best of all, you can often catch a play, comedy, or a musical at a great price, as Hot Tix sells half-price tickets online and at a few city locations.
North Michigan Avenue—also known as The Magnificent Mile—is a teen shopper's paradise, with everything from the Apple Store for some modern gadgets to Gap, Patagonia, Bloomingdale's, and Nordstrom for checking out clothes. Be sure to take a pit stop at Garrett Popcorn Shop for a bag of caramel, butter, or cheesy popcorn snacks, among other delicious flavors.
If you are visiting Chicago in the summer, you may want to grab your swimsuit and catch some rays on Lake Michigan, along with the locals. North Avenue Beach boasts impressive skyline views and a nice expanse of sand for sunning, plus a biking and running path for those restless adolescents. Castaways Bar and Grill, a boat-shaped beach house, is a good go-to place for sandwiches, salads, ice cream, and snacks.
Lake cruises are a dime a dozen, but Seadog Extreme cruise is a thrilling adventure, set to music and engaging commentary about the city. The fastest tour boat on Lake Michigan combines sightseeing with wind-in-your-hair, spray-in-your-face excitement from March through October, depending on the weather. Attendees must be at least 48 inches tall.
If you are up for splurging a bit, Chicago offers an adrenalin-based attraction all year for the adolescent and the rest of the family. From a helicopter, you'll see over 25 miles of the city landscape and landmarks from above. There is also an option to ride at night, taking in the lovely city lights. Children must be at least 5 to ride the helicopter, and at least one person in your reservation must be over 18.
Teens can find many fun things to do at Millennium Park, a hub in the heart of Chicago with cultural programs such as art, dance, and theater events, and amazing vistas and green spaces. This beautiful park has many enjoyable offerings for you and your children, from riding bikes to checking out the public art installations to stopping at a food truck and having a picnic.
Navy Pier is an ideal family destination, with the famous Ferris wheel called Centennial Wheel, which has stunning views of the Chicago skyline and Lake Michigan; IMAX movies; shopping; and festivals all year. The area also boasts restaurants like Bubba Gump Shrimp Company for seafood lovers, I Dream of Falafel for Mediterranean eats, and Ben and Jerry's for ice cream treats. Plus, teens will love the Aon Summer Fireworks every Wednesday and Saturday from Memorial Day through Labor Day.