Downtown

Start at the 1883 Monadnock Building (1)(53 W Jackson Blvd), the last skyscraper made without steel (back when “skyscraper” meant 11 stories). Head north on Dearborn Street and you’ll enter the Mies van der Rohe Federal Center (2)(Dearborn St between Jackson and Adams Sts) with its orange Alexander Calder sculpture. Take a right (east) on Monroe Street and hit the former Carson Pirie Scott building (3)(1 S State St), Louis Sullivan’s masterpiece. Continue north on State and check out the iconic buildings across the river: Bertrand Goldberg’s “corncob” Marina Towers (4) and Mies’s IBM Building (5), soon to be hidden by the Trump Tower (6), swiftly rising to 90 stories. Turn right (east) on Wacker Drive and hit the Michigan Avenue bridge, where you’ll take the stairs to the riverwalk for skyline views. Turn left and head west along the river. At the bend, look across the water: Graham, Anderson, Probst & White’s 1931 Merchandise Mart (7) boasts its own zip code. And 333 Wacker Drive (8) is a favorite for its spectacular curving glass facade. Double back and ascend the stairs at Michigan Avenue. Take a look at the Wrigley Building (9)(400–410 N Michigan Ave) with its 250,000 terra-cotta tiles. Run south beside the Michigan “streetwall,” then take a right on Jackson Boulevard and continue west. The mammoth structure to the right is the Sears Tower (10)(233 S Wacker Dr). Turn right (north) on Wacker Drive and go to Adams Street, then turn right (east) again. At Adams and LaSalle streets, see the Rookery (11) (209 S LaSalle St), Burnham & Root’s building with a Frank Lloyd Wright–designed lobby. Continue east on Adams, turn right (south) on Dearborn Street, and end where you started. —Madeline Nusser

Map illustration: Headcase Design

Start at the Cloud Gate(1) sculpture, a.k.a. “The Bean,” in Millennium Park. Head east on the park’s path around the Great Lawn toward Frank Gehry’s shiny, snakelike BP Bridge (2) (his only bridge to date). Cross Columbus Drive over the bridge, go south along Columbus, then turn left (east) at Monroe Street, crossing with the traffic light. Follow the lakefront sidewalk south along Lake Shore Drive all the way to the Shedd Aquarium (3). You’ll see Solidarity Drive, a divided parkway, with trees and flowers down the middle. Turn left (east) until it dead-ends at the Adler Planetarium (4). Face northwest for a spectacular view of the skyline and lake. Oooh and ahhh, then turn and run back the way you came.—Liz Plosser