The most well-known and scenic of Chicago's historic boulevards is arguably Lake Shore Drive. In the 19th century, Lake Shore Drive was a popular tree-lined carriage drive. Pedestrians strolled along the drive, resting and relaxing at benches that were scattered along the boulevard.

Following the popularization of the automobile, an increasing number of motorists began using Lake Shore Drive to cut through Lincoln Park. In 1937, the Park District turned Lake Shore Drive into the city’s first freeway. Today, Lake Shore Drive is an eight-lane, often-congested, modern highway, but because it is still technically a boulevard, its lanes are closed to most commercial traffic.