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#20: Aon Center
200 E. Randolph St.
(Edward Durell Stone, with Perkins + Will, 1973)
Chicago’s third- tallest skyscraper lost some of its luster after gray granite replaced its Carrara marble skin.
#19: John J. Glessner House
1800 S. Prairie Ave.
(Henry Hobson Richardson, 1887)
The great East Coast architect’s only surviving Chicago building, its intimidating façade cloaks an airy family haven.
#18: Chicago Water Tower and Pumping Station
806/811 N. Michigan Ave.
(William W. Boyington, 1866, 1869)
A symbol as much as a building, the castellated tower—a survivor of the great fire of 1871—is one of Chicago’s few remaining Boyington works.
#17: Marquette Building
140 S. Dearborn St.
(Holabird & Roche, 1893–1895, 1906)
The brick and terra cotta exterior exemplifies the Chicago style; its entrance and lobby (with its Tiffany mosaics) are among the city’s most stunning.
#16: Richard J. Daley Center
bounded by Washington, Dearborn, Randolph, and Clark streets
(C. F. Murphy Associates; Loebl, Schlossman & Bennett; Skidmore, Owings & Merrill, 1965)
Complemented by the now-beloved Picasso, the rust-colored Cor-Ten steel building rises 648 feet but contains only 31 roomy floors.
#15: Robert Morris Center
403 S. State St.
(William Le Baron Jenney, 1891)
Known historically as the Second Leiter Building, this proto-skyscraper’s steel-and-cast-iron frame—Jenney’s great innovation—led architecture into the modern era.
#14: Marina City
300 N. State St.
(Bertrand Goldberg Associates, 1962)
With their eye-catching corncob design, these twin towers kicked off yet another architectural renaissance in Chicago.
#13: Hotel Burnham
32 N. State St.
(ground floor: Burnham & Root, 1891; rest of building: D. H. Burnham & Co., 1895)
Known originally as the Reliance Building, its façade of broad bay windows anticipated the glassy towers of the later 20th century.
#12: Unity Temple
875 Lake St., Oak Park (Frank Lloyd Wright, 1909)
The cubist exterior cast in unadorned concrete gives way to an awe-inspiring inner chamber.
#11: Inland Steel Building
30 W. Monroe St.
(Skidmore, Owings & Merrill, 1957)
Clad in stainless steel and glass, this postwar gem achieved its open floor plan by banishing elevators and other service elements to a separate tower.