During the Great Migration (1916-1930), Bronzeville's Black LGBTQ population grew rapidly as African Americans moved north for better opportunities and to escape Southern racism. The anonymity of Chicago allowed for greater sexual freedom and acceptance within the community.

Tony Jackson, a gay blues pianist from New Orleans, epitomized this shift. Seeking a more accepting environment, he migrated to Chicago in 1912, becoming a key figure in Bronzeville's vibrant music scene. Jackson's presence and performances in notable venues like the Elite Cafes and Pekin Cafe transformed the cultural landscape, leaving a lasting impact on the neighborhood's social life and LGBTQ history.