Metropolitan Correctional Center in Chicago

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287 ft. While not very tall, this 1975 brutalist structure is one of the most distinctive and curious in the Chicago skyline. As its name suggests, it is a vertical prison skyscraper and its sharp triangular shape is designed to minimize the amount of time that it takes to patrol its corridors. Its prisoners have some of the prison world's best views as their exercise yard is located on top of the roof, although the narrow slits serving as windows do not allow such nice views from the cells. The
Address: 71 W Van Buren St