The most underrated family city in America. World-class museums, a lakefront that feels like an ocean, deep-dish pizza that will ruin all other pizza forever, and a skyline that belongs in an architecture textbook. Significantly cheaper than NYC or San Francisco.
Two real itineraries, built for families. Each one is ready to customize in TripDeck -- drag activities around, add your own ideas, share with your travel partner.
Best for a long weekend. Millennium Park, the Museum Campus, Navy Pier, and deep-dish pizza. You'll hit the highlights without rushing.
The full Chicago family experience. Museum Campus, Millennium Park, Navy Pier, plus the Museum of Science and Industry, Lincoln Park Zoo, and a beach day. No day feels rushed.
Chicago is the most underrated family city in America. Here's why it belongs at the top of your list.
The activities families actually remember. Sorted by "kids will talk about this for months" factor.
32,000+ animals. The Abbott Oceanarium with beluga whales and dolphins is breathtaking. Caribbean Reef is a 90,000-gallon circular tank you walk through. Polar Play Zone designed for ages 2-5. Get there at opening -- hits capacity by 11 AM on summer weekends.
The U-505 submarine (a captured WWII German sub you walk through) is thrilling. Coal mine goes 50 feet underground. Science Storms lets kids create mini-tornadoes and tsunamis. Idea Factory for ages 0-7. Give it a full day.
Sue the T. rex is the world's most complete T. rex skeleton. Evolving Planet goes from the Big Bang to present day. Ancient Egypt has an actual mummy. Crown Family PlayLab is excellent for ages 0-10.
A 33-foot reflective sculpture that warps the Chicago skyline. Kids run around it, make faces, stand underneath. Free and open 24/7. The most photographed thing in Chicago for good reason.
The Centennial Wheel Ferris wheel gives panoramic lake and skyline views. Chicago Children's Museum is one of the best in the country for ages 0-10. Free Tuesday evenings for Illinois residents. Rides, food, and waterfront views.
90-minute boat tour narrated by docents who make skyscraper history genuinely exciting. Tribune Tower, Marina City ("corn cob buildings"), Willis Tower. A surprise hit with kids 6+. Book the 9:30 AM departure for fewer crowds.
Free. Open year-round. The Farm-in-the-Zoo lets kids pet goats and see chickens. The Nature Boardwalk behind the zoo is a hidden-gem wetland loop. Smaller than big-name zoos, but the price (zero dollars) can't be beat.
103rd-floor glass-bottom Ledge boxes extend 4 feet out from the building. You stand on glass and look 1,353 feet down. Some kids love it, others refuse. Either way, the view is incredible.
These activities (and 20+ more) are already loaded in TripDeck. Drag them onto your days to build your schedule.
Open the 5-day plan →Chicago food is big, bold, and naturally kid-friendly. Deep-dish pizza, Chicago-style hot dogs, Italian beef sandwiches. Kids eat well here.
The locals' favorite deep-dish. Buttercrust is the signature -- flaky, buttery, different from every other deep-dish in the city. Multiple locations. Order as soon as you sit down (40-minute cook time).
Cult favorite with a caramelized cheese crust that creates a crispy, charred edge. The Lincoln Park location has the best atmosphere. Different level from the chain deep-dish places.
Chicago fast-food institution. Hot dogs, Italian beef, and the famous chocolate cake shake (a milkshake blended with a slice of chocolate cake). Multiple locations. Always packed, always worth it.
The original Italian beef since 1938. Order "dipped" (bread soaked in jus) for the authentic experience. Messy, flavorful, unforgettable. Little Italy location is the classic.
Chicago Mix (caramel + cheese popcorn combined) in the signature blue tin. Multiple downtown locations. Expect a line at the Magnificent Mile store. Great snack to bring to the hotel.
Not everything in Chicago is worth the time and money with kids. Here's where you might want to adjust.
Excellent. Lincoln Park Zoo is free. The Chicago Children's Museum on Navy Pier is specifically designed for ages 0-10. Crown Fountain is a free splash pad. The Museum of Science and Industry and Shedd Aquarium both have dedicated toddler areas. Chicago might be the best big city in America for toddlers.
3 days covers the Museum Campus, Millennium Park, Navy Pier, and deep-dish pizza. 4-5 days lets you add the Museum of Science and Industry, Lincoln Park Zoo, an architecture cruise, and a beach day. The city doesn't feel rushed at 4 days the way NYC does.
June through early September. You want lakefront weather -- warm enough for beaches, outdoor festivals, and Crown Fountain. The city comes alive in summer after a long winter. Late September is also nice but cooler. Avoid November through March unless you genuinely enjoy wind chills of -10 degrees.
The tourist areas (Loop, Museum Campus, Navy Pier, Lincoln Park, Magnificent Mile) are very safe. Chicago's crime issues are concentrated in specific neighborhoods far from where tourists go. Take normal city precautions -- don't walk alone in unfamiliar areas at night, keep your phone secure on the L train -- and you'll be fine.
Pick a trip length, then drag and drop activities to build your perfect family itinerary. Share the link with your travel partner -- changes sync in real time.
Or plan a custom trip with any dates and destination.