In 1849, John S. Wright, a real-estate investor, proposed an expansive system of parks connected by drives.

As anticipated, the park and boulevard system attracted real estate development and in the process created one of the city’s most recognizable and lasting urban features.

The system is locally significant because, for the first time in Chicago, urban growth was thoughtfully planned and executed on a city-wide scale.

The firm's principals, Frederick Law Olmsted and Calvert Vaux, designed park and boulevard systems for Boston (its Emerald Necklace), Buffalo, and other cities.

The West Chicago Commission's section of the system was designed by William Le Baron Jenney.

[5] Legal action against the Lincoln Park Commission prevented progress until widening Diversey Avenue to near Logan Boulevard became impractical.

[5] An international architectural-concept competition, Network Reset, awarded prizes in 2011 for "rethinking" the Chicago boulevards.

[14] The approved listing, stretches approximately 26 miles, including 8 parks, 19 boulevards, and 6 squares, as well as adjacent properties that preserve structures built from the 19th century to the 1940s.