Middle schoolers are typically in that active, curious, almost-teen phase where they want independence while having fun. In Chicago, there are plenty of safe and exciting spots built to match that energy: experiences that let them explore, challenge themselves and snap great photos for their social feed. For this list we reviewed family travel guides, tween-friendly blog posts and official attraction websites to pick eight standout destinations that work for this age group.
2025 Chicago Toy & Game Fair
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What kid doesn’t love toys and games? At the Chicago Toy & Game Fair, your middle-schooler can test out the newest toys and games, compete in yo-yo and kendama contests, meet their favorite characters and even play giant versions of games like Jenga. Whether they’re into strategy games, cool tech toys or just goofing around with friends, this is the middle school hangout of the season. Pro tip: Take your middle-schooler and their bestie and let them go wild (safely, of course.)
- Address: Donald E. Stephens Convention Center, 5555 N River Road, Rosemont
- Hours: 10 a.m.-6 p.m. Nov. 8 and 10 a.m.-5 p.m. Nov. 9
- Phone: (847) 677-8277
The Escape Game Chicago
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When your tween wants to feel like a hero on a mission, The Escape Game Chicago delivers with immersive escape-room adventures. Groups solve puzzles, decode clues and race against the clock in themed rooms. Think prison breaks or art heists which are perfect for collaborative tweens who enjoy problem-solving. It gives them agency, teamwork and a sense of accomplishment whether they win or not. Many reviews highlight how tweens feel empowered participating fully, rather than just tagging along. Pro tip: Let your tween be the leader in the group and encourage them to figure things out before stepping in.
- Address: 42 E Ontario St., Chicago
- Hours: 8 a.m.–midnight Monday-Thursday; 8 a.m.–1 a.m. Friday-Sunday
- Phone: (312) 453-7753
360 CHICAGO (formerly John Hancock Observation Deck)
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If your tween is ready for sky-high thrill and photo-worthy views, 360 CHICAGO offers floor-to-ceiling windows and a glass ledge experience where you can step out over the city. It combines architecture, geography and an exciting wow factor. Many travel guides recommend it for older kids and tweens who crave something more than just a playground. Pro tip: At 9 a.m.–10 a.m., the crowds are lighter so you’ll get better access and more relaxed time to explore together.
- Address: 875 N Michigan Ave., Chicago
- Hours: 9 a.m.–11 p.m. daily
- Phone: (888) 875-8439
WHIM! A Studio Space
If your tweens are ready to ditch screens and get their hands messy in the best way possible, WHIM – A Studio Space is the spot. From paint-your-own pottery to clay-building workshops, this Wheaton studio offers creative sessions for all ages — including the option to bring your creations home once they’re fired. Whether it’s a birthday party, an after-school escape, or a chill crafting morning, WHIM turns the studio into a family-friendly art adventure. Pro tip: Remind your tween that handmade items make great holiday gifts!
- Address: 120 W Wesley St., Wheaton
- Hours: Hours vary based on activity
- Phone: (630) 640-9442
Museum of Science and Industry
The Museum of Science and Industry is a fantastic destination: full-scale exhibits like submarine tours, tornado simulations and interactive experiments make science feel cinematic and real. It hits that sweet spot where kids feel like they’re on an adventure, not in a school lesson, and families can move at their own pace. Many sources recommend it for this age group specifically. Pro tip: Let them lead with a “choose-your-own-adventure” pick early on.
- Address: 5700 S Lake Shore Drive, Chicago
- Hours: 9:30 a.m.–4 p.m. daily
- Phone: (773) 684-1414
Maggie Daley Park: Skating Ribbon and Adventure Play
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Maggie Daley Park blends active fun with playful challenge — ideal for tweens who like to climb, skate or explore. The Skating Ribbon (in winter) or rock-climbing walls (in warmer weather) let them test skills in a fun public space. Reviews suggest this for tweens who aren’t little kids but aren’t full teens either. Pro tip: Start at the Play Garden so you build up energy and momentum, then head to the Skating Ribbon for the skyline drift before it gets crowded.
- Address: 337 E Randolph St., Chicago
- Hours: 6 a.m.–10 p.m. daily
- Phone: (312) 552-3000
The Sloomoo Institute (Slime Museum)
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For a lighter, quirky outing that still feels just-for-tweens, the Sloomoo Institute offers hands-on slime labs, sensory zones and photo-friendly installations. As one blogger notes, when the usual kid spots are too young and the teen spots too mature, this place hits the sweet spot. Pro tip: Wear clothes you don’t mind getting messy and plan the make-your-own slime part as the grand finale.
- Address: 820 N Orleans St., Chicago
- Hours: 11 a.m.–5:30 p.m. Monday-Thursday; 10 a.m.–6:30 p.m. Friday; 9 a.m.–7:30 p.m. Saturday; 9 a.m.–5:30 p.m. Sunday
Chicago Riverwalk & Urban Kayak Adventure
Older tweens love a dose of autonomy and the Chicago Riverwalk offers that: bike-rental access, kayak or paddleboard options, public art and prime photo spots. According to CityPASS, it’s one of the top tween-approved experiences in Chicago for blending fun, movement and city lifestyle. Pro tip: Book an early-afternoon kayak slot and choose the south-to-north direction so you finish near the Riverwalk and can keep the momentum going into a riverside stroll or snack break.
- Address: 435 E Chicago Riverwalk, Chicago
- Hours: Hours vary based on activity and business
- Phone: (312) 965-0035
