Experience Architectural Art with the Tallest Buildings in Chicago

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Chicago, Illinois is world-renowned for its upscale cuisine and street food, engaging public art pieces (like the famed Cloud Gate Sculpture in Millennium Park), and live concert venues. But the Windy City is perhaps most famous for its skyline. 

Some of the tallest buildings in the world are located downtown, crowding the Chicago skies with stunning examples of architectural design and ingenuity. As you take in the Chicago skyline, seek out these skyscrapers that remain some of the tallest buildings in Chicago. 

The Willis Tower (formerly known as the Sears Tower)

Up until 1998 when the Petronas Tower in Kuala Lumpur took the crown, the Willis Tower (known as the Sears Tower when it was first built) held the title of tallest building in the world for 25 years. This 108-story, 1,450-foot marvel paved the way for all the towering skyscrapers that came after it, and remains the tallest building in Chicago to this day. 

The tower is currently the third-tallest building in the United States (after being outpaced by the One World Trade Center and Central Park Tower, both in New York City) and the 23rd-tallest in the world. Though the skyscraper mostly houses office spaces, you can enjoy the views and feel your adrenaline skyrocket by stepping out onto the Skydeck Chicago ledge. You'll be able to see out over the Chicago skyline, with the city’s towering skyscrapers below your feet. 

875 North Michigan Avenue 

Formerly known as the John Hancock Center, the skyscraper at 875 North Michigan Avenue stands within the famed Chicago shopping district known as the Magnificent Mile. The 100-story, 1,128-foot standout on the list of the tallest buildings in Chicago features the city’s only open-air skywalk and America’s highest indoor swimming pool. It’s a stunning example of the structural expressionist style, completed in 1968 by civil engineer Faxlur Khan and architect Bruce Graham. 

St. Regis Chicago and Aqua Lakeshore East 

Jeanne Gang’s architectural firm is responsible for the towering beauty of both the St. Regis Chicago (formerly known as the Wanda Vista Tower) and the Aqua. The St. Regis is the 3rd-tallest building in the Windy City, while the Aqua sits at around 12. 

Both remain the tallest buildings in the world designed by a female architectural team, and stun viewers with a sense of rhythm and movement that is unmatched by the towering skyscrapers that surround them. Both are mixed-use hotel and residential spaces, giving you the opportunity to live within a majestic example of Chicago’s architectural history

Whether you seek out the tallest buildings in Chicago, Illinois along the Magnificent Mile or look to the Chicago skyline to take them in, you’re always within sight-distance of beauty when you’re in the Windy City. Continue to explore by checking out the broadway scene in Chicago, or experience history by visiting museums in the Loop.