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At 16 stories, this Holabird and Roche designed building (1891) is one of the world’s tallest all-masonry high-rises. Inside, there’s a magnificent wrought-iron staircase.

Holabird and Roche also built this 1894 Chicago School structure with a steel skeleton and decorative ornamentation.

Daniel H. Burnham’s stunning glass-and-white-glazed-terra-cotta building (1895) is now the Hotel Burnham.

Another Chicago School edifice with a steel structure, this 1896 neo-Gothic building is also by Daniel H. Burnham. Aquatic motifs on the façade honor the building’s first owner, L. G. Fisher.

Eye-catching cast-iron swirls on part of the exterior of this store (1899 & 1903) express architect Louis H. Sullivan’s love of elaborate detail (see Carson Pirie Scott & Co.).

Daniel H. Burnham designed this elegant high-rise in 1904: its carved building signs are from Chicago’s days as a railroad hub. The ground level houses the Chicago Architecture Foundation (see Chicago Architecture Foundation Shop).

The red marquee of this Beaux Arts-style theater is a symbol of Chicago. Built in 1921, today it is a concert and performance venue.

This 1930-built, 49-story building was Chicago’s tallest for 35 years, and is one of the city’s best surviving examples of Art Deco architecture.

One of the first skyscrapers to be built (in 1957) on steel, not concrete, pilings. It predated the John Hancock building (see John Hancock Center) in using external supports.

Flanked by Ludwig Mies van der Rohe’s federal buildings, this plaza (1959–74) contains Alexander Calder’s striking statue Flamingo (1974).