Jackie Ormes and her husband moved to Bronzeville, a predominantly Black neighborhood in Chicago's South Side, in 1942, and she continued to pursue art and journalism.
She interacted with the socially conscious artists of the Chicago Renaissance and contributed to the Chicago Defender, one of the nation's leading Black newspapers. In the 1950s, Ormes worked for the women's auxiliary of the Chicago Urban League, and joined the board of the South Side Community Art Center in 1953. Ormes' political awakening informed the content of her own art—for example, in Patty-Jo 'n' Ginger, five-year-old Patty-Jo often levied pointed criticisms at the House Un-American Activities Committee— prompting the FBI to compile a 287-page dossier on her.