Planning a trip to Chicago and dreading the inevitable eye-rolls and "I'm bored" whispers from your teens? The Windy City might just surprise you (and them!). We've put together the ultimate guide to making Chicago actually fun for your teen, packed with experiences that are definitely not lame. Get ready to swap their normal sighs for smiles, because we're talking epic views, interactive art, brain-bending museums, and, most importantly, food they'll actually want to eat.
After viewing downtown from the water, it’s time to head up, way up, for a bird’s eye view. 360 Chicago is a fantastic spot for teenagers looking for more than just a pretty panorama. Sure, the 94th-floor observation deck offers jaw-dropping 360-degree views of the Chicago skyline, Lake Michigan, and even four surrounding states on a clear day. But often the biggest attraction for teens is TILT! Imagine leaning out, face-first, over Michigan Avenue from 1,000 feet up! This enclosed, glass and steel platform slowly tilts outward, giving you a unique perspective of the city below. It's a safe but exhilarating experience that's a total blast.
Then stroll around the outdoor art exhibit featuring local artists. Plus, you can grab some cool drinks and snacks at CloudBar, including the teen-favorite mocktails Rainbow Beach and Midway, or other non-alcoholic beverages. Kick back together and toast the cityscape stretching out before you. And if you time your visit just right, you can do all this while catching a front-row seat to an awe-inspiring sunset.
Most everyone loves riding on a boat, even famously unagreeable teenagers. Add in extra points for insta-worthy views of Chicago’s famous landmarks that your teen can share with their friends back home. Along the way, expert guides will share the fascinating stories behind Chicago’s iconic architecture that appeal more to the parents.
Glide along the Chicago River, past masterpieces like the soaring Willis Tower, the unique corncob-shaped Marina City, the elegant Wrigley Building, and so many more, while learning how Chicago became a global architectural innovator. Whether you're an architecture buff or just looking for a super cool way to see the city with your kids, these 75-90 minute tours offer stunning panoramic views, comfortable seating (both open-air and climate-controlled), and often a cash bar for refreshments. If this isn’t thrilling enough for your family, you can up the adrenaline level with a speedboat tour on the Chicago River and Lake Michigan.
A lot of teens groan at the mention of touring an art museum, but The Art Institute of Chicago is actually packed with awesome stuff for teens. It's not just about staring at old paintings (though they have those too, and some are pretty cool!). Your family can kick things off by downloading their Teen Audio Guide on the official mobile app, where you'll hear other Chicago teens talk about the art. You can even use their "My Museum Tour" builder to create a personalized tour of your favorite pieces, maybe focusing on topics that interest your teen such as fashion, Black artists, or even mythical creatures.
Then head over to the ever-changing outdoor art gallery at the Wabash Arts Corridor in Chicago's South Loop. This place is a "living urban canvas" where ordinary building walls and alleys have been transformed into a massive showcase of incredible street art, murals, and installations. For teens, it's like a giant scavenger hunt for awesome photo ops and thought-provoking pieces. You can wander around discovering massive, colorful murals by local and international artists, often with cool messages or unique styles.
Columbia College Chicago students even get involved in creating new pieces, so there's always something fresh to see. It's totally free, super walkable, and gives you a chance to experience art in a totally different, dynamic way. There’s also dozens of restaurants nearby, so after exploring the art, you can walk over to a nearby restaurant and savor some delicious local cuisine.
At the Museum of Illusions, get ready for your brain to do some gymnastics. This place is all about visual tricks, optical illusions, and interactive exhibits that will have you questioning everything you view. Seemingly defy gravity in the Anti-Gravity Room or get lost in the dizzying Vortex Tunnel. Every exhibit comes with an explanation of the science behind the illusion, making it a cool blend of education and pure amazement.
Then at the Griffin Museum of Science and Industry, you can explore hands-on exhibits on everything from outer space to the depths of a coal mine. Teens will love stepping inside a real German U-505 submarine, experiencing simulated tornadoes and tsunamis in Science Storms, and exploring the incredible Great Train Story model railroad. You can even check out a real United 727 airplane!
At the Color Factory, prepare to be immersed in a world of pure imagination and, well, color. This interactive art experience is packed with unique rooms and installations that are designed to engage all your senses. Walk through vibrant ball pits, dance under confetti showers, snack on colorful treats, and discover whimsical spaces that are perfect for snapping epic, shareable photos.
And then there's the Sloomoo Institute, a dream come true for anyone who loves slime. Make your own custom slime at the DIY bar, explore different textures and scents, plunge your hands into giant slime vats, and even walk on a slime lake. For those who really want to be “immersed” in the slime experience, there’s Sloomoo Falls where you get to stand beneath, you guessed it, a slime waterfall.
No visit is complete without trying the famous Chicago-style deep dish pizza. Lou Malnati’s and Giordano’s are considered two of the best places to grab a slice (or two or three). What, exactly, is Chicago-style deep dish pizza? As the name suggests, it’s baked in a deep dish, with a thick buttery, flaky crust with a layered construction, often with cheese on the bottom and a thick layer of chunky tomato sauce on top—so come hungry!
Portillo’s hot dogs are another staple on the local food scene, and with numerous locations, you’re never far from their famous Chicago-style hot dog, which is a crowd pleaser for teens and parents alike. And if you’re wondering what a Chicago-style hot dog is, it has that classic “snap” in every bite. This comes from its many ingredients: sport peppers, kosher pickle, sliced tomatoes, chopped onions, celery salt, relish, mustard that are all piled on a juicy hot dog in a poppy seed bun.
And the best for last—vacation is the time to indulge in some delicious desserts. JoJo’s shakeBAR is one of the sweetest spots in town. There’s milkshakes, and then there’s JoJo milkshakes that look like sugary works of art almost too mesmerizing to eat. Snapping some pics with your shake is a must before digging in. They also serve hearty lunch and dinner dishes to balance out the sugar rush. Jeni’s Ice Cream is also a favorite summertime treat, with multiple locations offering scoops of delectable flavors like brambleberry crisp, sweet cream biscuits & peach jam, darkest chocolate, and the list goes on.
Chicago truly has something to spark even the most discerning teen's interest, from leaning into exhilaration at 360 CHICAGO and a speedboat architecture tour to immersive museums and delicious eats. Ditch the anxiety/exhaustion that can often accompany traveling with teens, embrace the adventure, and get ready to make some unforgettable family memories in Chicago. Your teenagers might even… dare we say it… thank you!
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