Oakley Park dates to at least 1950, by which time Chicago's Bureau of Parks and Recreation was leasing the park site from the Board of Education. The Chicago Park District took over the lease in 1959, and assumed full ownership in 1990. Although there is no record of the park's naming, the Bureau of Parks and Recreation often named parks for adjacent streets. Oakley Street takes its name from Charles Oakley (1792-1849), a trustee of the Illinois & Michigan Canal accused of using canal construction to create patronage jobs in the 1840s.

Located in the Chicago Lawn community, Oakley Playlot Park is a recreational destination totaling 0.48 acres and it is enjoyed by park patrons and their families.This park contains a playground with swings, slides, and climbing equipment.