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#30: Serta International Center
2600 Forbs Ave., Hoffman Estates
The architect Andrew Metter fused a Prairie-style vibe with a spare Miesian grace for this suburban corporate headquarters.
#29: Prudential Building
130 E. Randolph St.
(Naess & Murphy, 1955)
For years Chicago’s tallest building, this limestone behemoth initiated a revival of downtown construction, dormant since the Depression.
#28: NBC Tower
454 N. Columbus Dr.
(Skidmore, Owings & Merrill, 1989)
Adrian Smith’s contribution to the Cityfront Center development updated the 1930s Art Deco style.
#27: 333 West Wacker Drive
(Kohn Pedersen Fox, with Perkins + Will, 1983)
A mix of modern and classical design, William Pedersen’s green-class building mirrors the nearby bend in the Chicago River.
#26: Lake Point Tower
505 N. Lake Shore Dr.
(Schipporeit-Heinrich Associates, with Graham, Anderson, Probst & White, 1968)
Based on a Ludwig Mies van der Rohe design from 1921, its curving glass walls reflect the lakeside setting.
#25: Union Station
210 S. Canal St.
(Graham, Anderson, Probst & White, 1925; 1992 renovation, Lucien Lagrange Architects)
The station’s Great Hall is the last reminder of Chicago’s glory days as the country’s railroad hub.
#24: United Airlines Terminal One Complex
at O’Hare International Airport
(Murphy/ Jahn, with A. Epstein & Sons, 1987)
The soaring barrel-vaulted concourses dazzle—but don’t overlook Helmut Jahn’s functional design.
#23: Wrigley Building
400 N. Michigan Ave.
(Graham, Anderson, Probst & White, 1920, 1924)
Brightly illuminated at night, this wedding cake of a building defies categorization.
225 N. Columbus Dr.
(Studio Gang Architects, 2009)
Universally praised for its visual and technical innovation, Jeanne Gang’s rippling Lakeshore East skyscraper found an immediate home on the skyline.
#21: Tribune Tower
435 N. Michigan Ave.
(Howells & Hood, 1925)
Built from a design selected from more than 250 entries to a 1922 contest, this neo- Gothic tower serves as a gateway to the Magnificent Mile.