America's Most Scenic Roads
Lake Shore Drive, Chicago
The rock stars of American architecture line up like soldiers facing Lake Michigan, starting north at Hollywood and reaching south through Jackson Park, spanning 26 miles. But the downtown buildings are showstoppers, from the blocky staircase of the Willis Tower—formerly the Sears Tower and tallest building in the world—to the Belle Époque elegance of Burnham and Root’s Rookery, to the stark post-Bauhaus boxes of Mies van der Rohe. It is the greatest architecture road on earth.
Stop: In Millennium Park, listen to free summer concerts under Frank Gehry’s fretwork bandshell. (grantparkmusicfestival.com; free admission.)