A pair of cheetah print sneakers on Skydeck in Chicago with the city street visible below.

Top Family-Friendly Sights and Landmarks in Chicago

A pair of cheetah print sneakers on Skydeck in Chicago with the city street visible below.

Top Family-Friendly Sights and Landmarks in Chicago

Chicago is filled with some of the best family-friendly sights and landmarks. Be sure to add these popular attractions to your upcoming travel itinerary.

With magnificent museums, beautiful beaches, and spectacular skyscrapers, Chicago is packed with incredible adventures for families that are designed to delight, excite, and intrigue visitors of all ages. The Windy City is known for doing things in a big, bold way, so it’s only natural for your vacation to be just as memorable as the town itself. Choose from experiences that boost the fun and cool quotient at top family-friendly sights and landmarks as you plan an unforgettable family vacation in Chicago.

The Chicago skyline towers over Lincoln Park on a partly cloudy day with a view of a green park and foliage.

1. Walk on Air at Skydeck Chicago

If your family likes heights and thrills, then don’t miss the Skydeck Chicago experience. Zip up to the 103rd floor of Willis Tower to take in the incredible views from the Skydeck, soaring 1,353 feet up above the city. Brave souls can even venture out onto the Ledge, a glass, see-through balcony with a view that’s certain to make your heart beat a little faster.

You can see all the top Chicago landmarks from the top, including Millennium Park and Wrigley Field, and the view extends miles beyond the city on cloud-free days. The sparkling views at night are beyond spectacular, too. You can also enjoy hands-on displays and activities that will engage the family while learn fascinating facts about Chicago through fun games and scavenger hunts at Skydeck Chicago.

Two penguins perch on a rock ledge during the day at the Field Museum in Chicago.

2. Explore the Field Museum of Natural History

Natural and human-made wonders are on display at one of the most acclaimed museums in the country, and they’re yours to explore with the Field Museum of Natural History Discovery Pass.

Whether you like shimmering gems, ancient Egyptian mummies, meteorites, dinosaurs, or Aztec temples, there’s something to fascinate and stir the curiosity and imagination of every family member at Chicago’s world-famous Field Museum of Natural History.

Choose from more than 35 awe-inspiring exhibitions, including SUE, the massive T. Rex, as you explore vast collections of intriguing artifacts. Your family can even discover what it’s like to be the size of an ant with the museum’s fantastic Underground Adventure experience. When stomachs start to rumble, choose from tasty fare at the museum’s two restaurants or an outdoor grill. After you refuel, there’s still so much more to explore.

Three bikes on green grass with the buildings of downtown Chicago across the river on a sunny day.

3. Take the Kids on a Bicycle Tour

This guided biking tour spins along at a safe, kid-friendly pace on Chicago’s bike paths and sidewalks, making stops at popular spots on the way. You get helmets and bikes that are just the right size for the different members of your family, and you can try out your gear before taking off.

You’ll bike along the lovely Lakefront Trail to Lincoln Park and the acclaimed Lincoln Park Zoo, complete with a popular petting zoo. The amazing sights include the Navy Pier Ferris Wheel, Lake Michigan, an enormous statue of Abraham Lincoln, a secret garden, and the sand and surf at both Oak Street Beach and North Avenue Beach. The tour wraps up with a special ceremony and prizes — just for the kids — that are sure to bring smiles to young faces.

Take your trip to Chicago to the top, and discover the best premium experiences a family getaway can offer when you sign up for Hertz Gold Plus Rewards.

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