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2. Chicago

If New York City is the Batman of U.S. skylines, then Chicago is the Robin. Located on the southern tip of Lake Michigan, Chi-town is home to a number of remarkable buildings, including the world’s first skyscraper in the Home Insurance Building. Following the Great Chicago Fire of 1871, the city saw a boom in high-rise construction as it attempted to rebuild itself from the ground up. Today, the Willis Tower and the Trump International Hotel and Tower are just two of the many notable buildings that line this incredible skyline.

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