Map: The Loop, Chicago

The heart of Chicago’s downtown financial center is called The Loop for the elevated train line that rings the district. It is home to some of Chicago’s first experiments in building the skyscraper and represents an early affinity for public art later embodied by Millennium Park.

Begin your walk at Jackson Boulevard and Dearborn Street, home to the (1) Monadnock Building (53 W. Jackson Blvd.), the north part of which was designed by architects Burnham and Root, considered the world’s tallest masonry building in which six-foot (two-meter) walls at the base support 17 stories above on the north wing and a steel-frame structure on the south represents the move to modern materials.

Continue on Jackson past the (2) Chicago Board of Trade Building (141 W. Jackson Blvd.), a Holabird and Root art deco landmark that foots LaSalle Street. Walk north a block to the (3) Rookery Building (209 S. LaSalle Street), another Burnham and Root transitional building in the history of architecture that employs both masonry and steel frame. Step into the sky-lit lobby, which architect Frank Lloyd Wright remodeled in Prairie style in 1905.

Return two blocks east to Dearborn along Adams Street to the (4) Kluczynski Federal Building (230 S. Dearborn Street) by Ludwig Mies van der Rohe of “less is more” fame. The plaza here hosts the first in a series of public “sculptures (which) are site specific and work in counterpoint with the surroundings to enliven the public realm.”—Blair Kamin, architecture critic, Chicago Tribune. Here Alexander Calder’s 53-foot (16-meter) red steel (5) Flamingo arches gracefully over the plaza in contrast to the government building’s 42-story rational rectangle above.

Next, walk north to the (6) Marquette Building (140 S. Dearborn Street), an 1895 Holabird and Roche skyscraper that celebrates its steel construction with a seemingly light structure of broad windows. Continue north on Dearborn between Monroe and Madison Streets to (7) Chase Tower plaza (10 S. Dearborn Street), home to a curving, 60-story skyscraper and (8) The Four Seasons (Dearborn and Monroe Streets), a mosaic installation by artist Marc Chagall.

Follow Dearborn again to Washington Street where the (9) Daley Center (50 W. Washington Street) hosts another international style high-rise based on the works of van der Rohe and the 1967 (10) untitled Picasso sculpture created and donated to the city by Pablo Picasso. The interactive and enigmatic metal statue—resembling a dog or an aardvark, depending on whom you quiz—is popular with the playful, who like to slide down it.

Exit Daley Plaza on the Clark Street side and walk one block north to the (11) James R. Thompson Center (100 W. Randolph Street), a metal and glass rotunda by Helmut Jahn. Its plaza hosts artist Jean DuBuffet’s (12) Monument with Standing Beast, a marzipan-looking white fiberglass structure you can walk in and around. Return east two blocks past the theaters in the area and south one block on State Street to finish with a bite at the (13) Atwood Café (1 W. Washington Street; www.atwoodcafe.com) located in the Hotel Burnham, an early skyscraper from, again, Daniel Burnham.

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