10 Iconic Chicago Buildings You Don’t Want to Miss

Chicago is the birthplace of the skyscraper, and its skyline is a living museum of architectural innovation. From 19th-century landmarks to bold modern designs, every block has something worth looking up at.

Here are 10 iconic Chicago buildings you need to see — complete with locations, costs, and insider tips.

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1. Willis Tower (aka Sears Tower)

The big one. Once the tallest building in the world, Willis Tower remains Chicago’s most famous skyscraper. The Skydeck on the 103rd floor offers sweeping views, and The Ledge — glass boxes that extend over the city — are a must-try thrill.

📍 233 S Wacker Dr, Chicago, IL 60606
💵 Tickets: From $32 adults / $24 kids (book online)
🕒 Hours: 9 AM – 10 PM daily
✨ Pro tip: Go at sunset for skyline + night views. On clear days, you can spot four states.

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2. 875 North Michigan (formerly John Hancock Center)

Known locally as The Hancock, this tower rises above the Magnificent Mile. Its 94th-floor observation deck is famous for lakefront views. For adrenaline junkies, TILT leans you out over Michigan Avenue in a moving glass platform.

📍 875 N Michigan Ave, Chicago, IL 60611
💵 Tickets: From $30 adults / $20 kids
🕒 Hours: 9 AM – 11 PM daily
✨ Pro tip: Visit at twilight for the perfect mix of city lights and lake blues.

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3. The Rookery

This 1888 gem, updated by Frank Lloyd Wright in 1905, is one of the most beautiful office buildings in America. The light court and grand staircase make it a photographer’s dream.

📍 209 S LaSalle St, Chicago, IL 60604
💵 Lobby access: Free | Tours: $10–$20
🕒 Hours: Mon–Fri, 9 AM – 5 PM
✨ Pro tip: Book a guided tour to get full access.

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4. Chicago Cultural Center

One of the best free things to do downtown. Inside you’ll find the world’s largest Tiffany glass dome, ornate staircases, and free concerts and art exhibits.

📍 78 E Washington St, Chicago, IL 60602
💵 Cost: Free
🕒 Hours: Daily, 10 AM – 5 PM
✨ Pro tip: Pair it with Millennium Park right across the street.

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5. Tribune Tower

This Gothic Revival tower is a scavenger hunt in stone. Embedded in its walls are fragments from over 150 world monuments — including the Great Wall of China and the Berlin Wall.

📍 435 N Michigan Ave, Chicago, IL 60611
💵 Cost: Free to view from outside
🕒 Anytime
✨ Pro tip: Walk around the base to spot the labeled stones.

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6. Wrigley Building

A Chicago postcard in real life. Its terra-cotta façade gleams by day, and the clock tower glows beautifully at night.

📍 400–410 N Michigan Ave, Chicago, IL 60611
💵 Cost: Free
🕒 Anytime
✨ Pro tip: The best photo spot is from the Michigan Avenue Bridge or the Riverwalk.

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7. Aqua Tower

Designed by Jeanne Gang, Aqua’s wavy balconies make it one of Chicago’s most distinctive modern buildings.

📍 225 N Columbus Dr, Chicago, IL 60601
💵 Cost: Free to admire from the street
🕒 Anytime
✨ Pro tip: Look up from Columbus Drive for the best view.

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8. Marina City (aka “The Corn Cobs”)

These mid-century twin towers are part apartments, part parking garage, and total Chicago icons.

📍 300 N State St, Chicago, IL 60654
💵 Cost: Free to view
🕒 Anytime
✨ Pro tip: The Dearborn Street Bridge offers the best angle for photos.

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9. Chicago Board of Trade

Capping LaSalle Street, this Art Deco tower is topped with a statue of Ceres, goddess of agriculture. The symmetry of the street leading to it makes it a movie favorite.

📍 141 W Jackson Blvd, Chicago, IL 60604
💵 Cost: Free to admire from outside (tours offered during Open House Chicago)
🕒 Anytime
✨ Pro tip: Go early for a clean “LaSalle Street canyon” shot with no traffic.

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10. Carbide & Carbon Building

This black-and-gold tower was allegedly designed to resemble a champagne bottle. Today it houses the Pendry Chicago Hotel, but the Art Deco lobby is open to visitors.

📍 230 N Michigan Ave, Chicago, IL 60601
💵 Cost: Free to enter the lobby
🕒 Anytime
✨ Pro tip: Visit at night — the gold top glows brilliantly against the skyline.