10 Chicago Landmarks No Visitor Wants to Miss

By: Lena Thaywick  | 
You can get a stellar view of sunset from the Willis Tower Skydeck. Salvador Maniquiz / Shutterstock

Chicago is packed with some of the most celebrated sights in the United States. From the glimmering lakefront to the towering skyscrapers, Chicago landmarks tell a vibrant story of architecture, innovation and culture that you can experience all in one epic city.

Want to design the ultimate itinerary? Let's step into the Windy City and explore 10 iconic attractions that mix historical significance, art and good old-fashioned fun.

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1. Willis Tower and Skydeck Chicago

Once the tallest building in the world, the Willis Tower (formerly Sears Tower) stands at 1,450 feet (442 meters). It’s not just a marvel of engineering but also home to Skydeck Chicago, where brave visitors step onto The Ledge — glass boxes extending from the 103rd floor.

The view offers a sweeping panorama of the city blocks, Lake Michigan and beyond. Don’t forget to book ahead if you want to avoid the line.

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2. Millennium Park and The Bean

bean
The Bean in Millennium Park. MattariStudio / Shutterstock

Located in the heart of downtown, Millennium Park is one of Chicago’s most photographed spots. Its shining star? Cloud Gate, affectionately called "The Bean" due to its curved, reflective surface. It’s more than a sculpture—it’s a selfie magnet and a symbol of modern design in a historic city.

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3. Navy Pier and Pier Park

Stretching into Lake Michigan, Navy Pier is a cultural and entertainment hub. Here, you can ride the Centennial Wheel at Pier Park, enjoy waterfront restaurants and catch live shows. This landmark pier is a popular site for locals and tourists looking to enjoy scenic views and family-friendly activities.

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4. Field Museum

At the Field Museum, science meets storytelling. This world-renowned institution is home to Sue, the most complete Tyrannosaurus rex skeleton ever found.

The exhibits delve into natural history, from ancient Egypt to the biodiversity of the Midwest. It’s a great place for adults and kids to learn together.

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5. Wrigley Field

Wrigley Field
Wrigley Field. Joseph Hendrickson / Shutterstock

No list of famous landmarks in Chicago is complete without Wrigley Field. Opened in 1914, it’s one of the oldest ballparks in Major League Baseball. Whether you’re a diehard Cubs fan or just here for the hot dogs and ivy-covered walls, this iconic stadium delivers a dose of classic American sport.

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6. Chicago Riverwalk

The Chicago River runs through the city's architectural heart, and the Riverwalk lets you explore it up close. This scenic path offers access to restaurants, boat tours and public art installations.

It’s a living testament to urban development that blends leisure and landscape.

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7. Art Institute of Chicago

This museum is a heavyweight in the world of art, housing everything from Grant Wood’s "American Gothic" to Seurat’s "A Sunday on La Grande Jatte." Located near Millennium Park, it’s a cultural gem that showcases designations from around the world.

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8. The Historic Pullman District

Commissioned in the 1880s as a model industrial town, the Pullman District is now a National Monument. It’s a great place to check out historic buildings and learn about labor history, urban planning and architectural innovation.

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9. Lincoln Park and the Conservatory

Lincoln Park stretches along the north side of the city and is home to a lush conservatory, the Lincoln Park Zoo, and scenic spots for picnicking. It’s the perfect park to visit if you want to spend time outdoors without leaving the city.

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10. Broadway in Chicago

Want to catch a world-class show without flying to New York? Chicago’s theater scene thrives thanks to Broadway in Chicago, which hosts big-name productions in some of the city’s most historic theaters. Check your dates as some shows are here for only a limited time.

We created this article in conjunction with AI technology, then made sure it was fact-checked and edited by a HowStuffWorks editor.

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