When playwright Lorraine Hansberry was a child in 1937, her family moved into a home in Woodlawn. Their case fighting the covenants went all the way to the U.S. Supreme Court, and the Hansberry's won. The events inspired her play, A Raisin in the Sun––the first Broadway play by a black woman.
But white flight and redlining soon followed, and Woodlawn has since experienced the fallout from disinvestment. Once a population of over 80,000, Woodlawn now has 23,000 residents, according to 2019 data.