The West Park System of Chicago was created in 1869. Comprised of Douglass, Garfield, and Humboldt parks and their connecting boulevards, the system was laid out by architect William Le Baron Jenney in 1871. Jenney transformed the marshy site for Douglass Park into a Picturesque assemblage of lagoon, lawn, and trees. The first section of the 173-acre park opened to the public in 1879. By the turn of the century, park embellishments included a conservatory, ornamental gardens, and the city’s first public bathing facility, complete with a swimming pool, outdoor gym, and a natatorium (no longer extant). Additional improvements were made by Jens Jensen in 1905 and 1910, including a formal garden, and a shelter building known as “Flower Hall.” A field house was added in 1928. The park is currently under consideration for listing in the National Register as part of the Chicago Historic Park Boulevard nomination.
In 2020, advocacy by local students resulted in the renaming of the park in honor of abolitionists Anna and Frederick Douglass. The park's former name was an homage to Illinois senator Stephen Douglas.