Landscaped with long vistas and avenues of trees at the start of the 20th century, the Midway in part followed the vision of its designer Frederick Law Olmsted, one of the creators of New York City's Central Park, but without his proposed feature of a Venetian canal down the Midway's center linking the lagoon systems of Jackson and Washington parks.

Instead, the Midway is landscaped with a fosse, lawn covered depression, where the canal would have been, although in the winter parts of the grounds are turned over for ice skating.

The firm of Olmsted, Vaux, and Co., famous for creating New York City's Central Park, was hired to design the urban oasis.

The expense of rebuilding the city eliminated the funds to cover expenditures that the plans would have entailed, and the South Park area remained largely in its natural swampy state.

For the Exposition, the mile-long Midway Plaisance, running from the eastern edge of Washington Park on Cottage Grove Avenue to the western edge of Jackson Park on Stony Island Avenue, was turned over to the theatrical entrepreneur Sol Bloom, a protégé of Chicago mayor Carter Harrison III.

It became a grand mix of fakes, hokum, and the genuinely educational and introduced the "hootchy-cootchy" version of the belly dance in the "Street in Cairo" amusement; it was the most popular, with 2.25 million admissions.

The Midway also featured more scholarly exhibits which were overseen by Frederic Ward Putnam, head of Harvard University’s Peabody Museum of Archaeology and Ethnology, and ethnologist Otis Tufton Mason of the Smithsonian Institution.

The sunken panels, home now to soccer players and ice skating and sports facility, the cross-street "bridges", and the east–west lines of trees, pay homage to Olmsted's vision.