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Chicago's Most Iconic Skyscrapers

© Ken Lund/Flickr
© Ken Lund/Flickr
Picture of April McCallum
Updated: 28 May 2019
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Frank Lloyd Wright said it best when he said ‘Eventually, I think Chicago will be the most beautiful great city left in the world’. Chicago’s skyline has been one of innovation and is regarded by many as being the birthplace of the modern skyscraper by innovating the steel-frame method. By using this method, Chicago housed the world’s first skyscraper in 1885 with the Home Insurance Building. This culture of invention has continued for over a century since then with the iconic skyscrapers that shape the city today.

Willis Tower

Building
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Willis Tower, South Wacker Drive
Willis Tower, South Wacker Drive | © arlexitus/Flickr
Formerly, and perhaps more widely known as Sears Tower, this 1,451-foot tall skyscraper was the tallest building in the world for 25 years until 1998. The tower is still the tallest building in the city of Chicago, meaning that its Skydeck is the ultimate viewing point of the city. Willis Tower was the first building to use Fazlur Rahman Khan’s bundled tube structure, allowing them to build the tower taller at a cheaper price.
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John Hancock Center

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John Hancock Center, North Michigan Avenue
John Hancock Center, North Michigan Avenue | © Sam Howzit/Flickr
The most distinctive aspect of this tower, besides its height, is its x-braced exterior, which helps it reach its height of 100 floors and open up its interior floor plan. Thanks to its close proximity to Lake Michigan, the Hancock building’s observatory provides a one-of-a-kind view of the city’s lakeshore and beyond.
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Tribune Tower

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Tribune Tower, North Michigan Avenue
Tribune Tower, North Michigan Avenue | © Bernt Rostad/Flickr
Chicago’s Tribune Tower is a beautiful neo-Gothic design that reaches 462 feet and has carved gargoyles of Robin Hood, a howling dog, and a frog, as references to the people behind the building’s construction. Although ornate buttresses surround the building’s peak, the most unique aspect of this building is at street level. As you walk the perimeter of the tower, you’ll find fragments of famous buildings embedded into the stone exterior walls. Each fragment is labeled with its origin and includes stone from the Berlin Wall, the Taj Mahal, Notre Dame Cathedral, the Great Pyramids and more.
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Trump International Hotel & Tower

Budget Hotel
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While many Chicagoans bemoan the addition of the two-story tall lettering of the tower’s namesake to the side, there’s no denying that it is a beautiful glass structure. The tower is located on the Chicago river, meaning it is not crowded on all sides by other buildings, giving it windows more of a chance to reflect the blue of the sky. With 98 floors, that’s a lot of blue.
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Radisson Blu Aqua Hotel

Hotel
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Radisson Blu Aqua Hotel, Chicago
Radisson Blu Aqua Hotel, Chicago | © JohnPickenPhoto/Flickr
Although only recently completed in 2009, the Radisson Blu Aqua Hotel has already claimed its spot as an iconic Chicago skyscraper. It received the Emporis Skyscraper Award for 2009 skyscraper of the year, as well as being shortlisted for the biennial International Highrise Award in 2010. It’s easy to see where the building gets its name from its wave-inspired design. This creates a perfect juxtaposition with nearby Lake Michigan.
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Crain Communications Building

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Although not as old or visually stunning as some skyscrapers on this list, the Crain Communications Building is one of the most unusually shaped buildings in the city, making it an iconic part of the Chicago skyline. Its slanted façade is what makes this building what it is, and also provides a flat surface to display messages for the public like ‘GO SOX’. It’s also unofficially known as both the ‘Diamond Building’ and the ‘Vagina Building’, the latter name is due to many people incorrectly interpreting that the building’s strange design was to counter the inherent phallic nature of most skyscrapers.
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Marina City

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Completed in 1964, these twin towers were the first buildings in the USA to be constructed with tower cranes. At the time of opening, these corn cob-shaped structures were the tallest residential buildings in the world. Marina City is located next to the Chicago River and contains a marina in the lower levels, while the complex’s original movie theater was converted into a House of Blues concert hall.
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Mon:
9:00 am - 6:00 pm
Tue:
9:00 am - 6:00 pm
Wed:
9:00 am - 6:00 pm
Thu:
9:00 am - 6:00 pm
Fri:
9:00 am - 6:00 pm

Wrigley Building

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The Wrigley Building, Chicago
The Wrigley Building, Chicago | © Benjamin Davidson/Flickr
The Wrigley Building is located at the southern beginning point of the Magnificent Mile and is across the street from the Tribune Tower. Composed of two towers with walkways at the first, third, and fourteenth floors, its distinguishing image comes from its gleaming white facade from its glazed terra-cotta and a clock tower with 19-foot clock faces on each side.
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Mon:
8:00 am - 6:00 pm
Tue:
8:00 am - 6:00 pm
Wed:
8:00 am - 6:00 pm
Thu:
8:00 am - 6:00 pm
Fri:
8:00 am - 6:00 pm
Sat:
8:00 am - 12:00 pm
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