Chicago's Best Architecture Walk

The Great Fire of 1871 could have been the death of Chicago, but instead it proved to be a grand rebirth. Renowned architects treated the decimated urban landscape as a fresh palette for their innovative ideas, sparking a revolution that has never really ended. Chicago's skyline is one of the city's most precious attributes, ever-changing but always awe-inspiring.

Tall Buildings of Every Size

Chicago is the home of the modern skyscraper, so start your tour at Wacker Drive and Adams Street at the city's tallest building, the Willis Tower (aka the Sears Tower). The 1,454-foot giant was the tallest building in the world when it was finished in 1973. Then head to the famous Rookery Building. This 12-story stunner, completed in 1888 by Daniel Burnham and John Welborn Root, is the oldest standing high-rise in town. On Jackson, check out the 45-story art deco Chicago Board of Trade, designed by Holabird & Root in 1930.

Chicago School and Modern Contrasts

Also on Jackson Street is Burnham and Root's 17-story Monadnock Building. Built in 1891, it's the last and tallest skyscraper built with masonry load-bearing walls. Head to Congress Parkway and Wabash Avenue to see Louis Sullivan and Dankmar Adler's Auditorium Building, a grand theater completed in 1889 that still hosts performances. These buildings are evidence of Chicago School architecture, which combined modern design practices of the time with traditional ideas like brick facades and ornamentation.

For a lesson in contrast, double back to Jackson and Dearborn streets to see the orderly, geometric 4.6-acre Federal Center, which was completed in the early 1970s by Mies van der Rohe. Don't miss the graceful slopes of Chase Tower, built in 1969 as the First National Bank of Chicago Building.

Stores and Centers

The Sullivan Center, at State and Madison streets, was Louis Sullivan's last major work in Chicago; note the elaborate cast-iron entryway ornamentation and three-part "Chicago Window," allowing plenty of light. Walk along State Street, past the Reliance Building (now the Hotel Burnham). This building is considered the first-ever glass-and-steel skyscraper. On the northeast corner of State and Washington streets, stop and admire Macy's, designed by Burnham in 1907 and most famous for the multistory atriums inside, one domed with a Tiffany mosaic.

Walk west on Randolph Street to reach the 648-foot Richard J. Daley Center at Clark Street, the tallest building in Chicago for four years until the John Hancock Center was built in 1969. Across Randolph is Helmut Jahn's dome-shape James R. Thompson Center.

Corncobs and High-Profile Towers

Head north on Clark Street, then east along the Chicago River to see Marina City, Bertrand Goldberg's pair of 61-story corncob-like apartment towers. Along the river at Kinzie Street is Trump International Hotel & Tower, a 1,389-foot skyscraper condo-hotel complex that was initially designed to be the world's tallest building before the events of 9/11.

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