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Green roof of Harold Washington Library Center behind Fisher, Old Colony, Plymouth & Manhattan buildings, the oldest skyscrapers in Chicago.
| South Dearborn Street with oldest skyscrapers Fisher, Old Colony, Plymouth & Manhattan buildings.
| Manhattan Building (1891) (16 floors) (431 South Dearborn St.) which when completed was tallest building in the world. Architect: William Le Baron Jenney.
| Detail of bay windows of Manhattan Building.
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Plymouth Building (1899) (11 floors) (417 South Dearborn St.). Architect: Simeon B. Eisendrath.
| Monadnock Building (1891) (17 floors) (53 West Jackson Boulevard), tallest masonry building in Chicago with walls at base six feet thick. Architect: John Wellborn Root of Burnham & Root + Holabird & Roche.
| Fisher Building (1906) (20 floors) (343 South Dearborn St.). Architect: D.H. Burnham & Co. + P.J. Weber.
| Terracotta decoration of Fisher Building.
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Bay windows of Fisher Building.
| Carved dragons decorating Fisher Building.
| Old Colony Building (1894) (16 floors) (407 South Dearborn St.). Architect: Holabird & Roche.
| Dearborn Street Station (1885) (47 W. Polk St.). Style: Romanesque Revival. Architect: Cyrus L. W. Eidlitz.
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