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#10: Sears Tower
233 S. Wacker Dr.
(Skidmore, Owings & Merrill, 1974)
The city’s giant is an engineering marvel—and I will never, ever, refer to it as the Willis.
#9: Farnsworth House
14520 River Rd., Plano
(Ludwig Mies van der Rohe, 1951)
A transcendent modernist masterpiece, this glass-walled single-story, single-room house floats elegantly alongside the Fox River.
#8: Frederick C. Robie House
5757 S. Woodlawn Ave.
(Frank Lloyd Wright, 1909)
Prairie style perfected—even Wright had to move in other directions or risk repeating himself.
#7: Auditorium Building
430 S. Michigan Ave.
(Adler and Sullivan, 1889)
Adler’s engineering skills and Sullivan’s design savvy concocted a feast for the ears and the eyes.
#6: S. R. Crown Hall
3360 S. State St.
(Ludwig Mies van der Rohe, with Pace Associates and C. F. Murphy Associates, 1956)
Mies’s clear-span design captures space and light within a deceptively simple glass box defined by steel columns and girders.
#5: Carson, Pirie, Scott & Company
1 S. State St.
(Louis H. Sullivan, 1899, 1903; D. H. Burnham & Co., 1906; Holabird & Root, 1961; major restorations in 1980 and 2010)
Rising from richly ornamented ground floors, the former department store’s spare upper stories showcase serene rows of light-luring Chicago windows.
#4: Monadnock Building
53 W. Jackson Blvd.
(northern half: Burnham & Root, 1891; southern half: Holabird & Roche, 1893)
Massive, austere, and exciting, its mix of steel frame and load-bearing walls signaled the onset of a new age in architecture.
#3: 860–880 North Lake Shore Drive
(Ludwig Mies van der Rohe, with Pace Associates and Holsman, Holsman, Klekamp & Taylor, 1952)
Startling in their day, these 26-story glass towers established the Mies aesthetic and influenced architecture around the world.
#2: The Rookery
209 S. LaSalle St.
(Burnham & Root, 1885–1888; lobbies and light court: Frank Lloyd Wright, 1907)
The celebrated skylit atrium and spiral staircase can unfairly overshadow the building’s audacious exterior and Root’s unseen but ingenious floating foundation.
#1: John Hancock Center
875 N. Michigan Ave.
(Skidmore, Owings & Merrill, 1969)
Bruce Graham, the architect, and Fazlur R. Khan, the structural engineer, paired big-shouldered brawn with cross-braced panache in this defining skyscraper of the second Chicago school of architecture.