The Willis Tower—formerly known as the Sears Tower—and the Pittsfield Building, among other skyscrapers, form part of the Chicago skyline.

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The Wabash Building, a part of Roosevelt University, and 333 South Wabash, previously known as the CNA Center, are notable landmarks in Chicago. The Wabash Building stands out with its 32-story glass structure offering panoramic views of the city, while the iconic 333 South Wabash, also referred to as "Big Red," is recognized for its distinctive red façade and modernist architectural style. Both buildings contribute to the architectural diversity and skyline of Chicago.

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This broadcasting mast extends into the Chicago skyline from One Prudential Plaza, while the distinctive angled architecture of Two Prudential Plaza casts its presence in the background. One Prudential Plaza, a 41-story skyscraper completed in 1955, was significant as the first new downtown skyscraper in Chicago in 21 years and served as the headquarters for Prudential's Mid-America company. Its mast was once used as a broadcasting antenna for Chicago's WGN-TV. Two Prudential Plaza, completed in 1990, stands out with its stacked chevron setbacks and a pyramidal peak rotated 45 degrees, crowned with an 80-foot spire.

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Chicago's Aon Center and adjacent buildings in the night sky over Illinois.

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A stairway climbs a building in Chicago.

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