Chicago's Grant Park Music Festival, a free classical music series, provides a case study for exploring how music festivals contribute to the musical life of cities. Each summer, the Grant Park Music Festival Orchestra and Choir perform dozens of free performances at the Jay Pritzker Pavilion in Millennium Park and in residential neighborhoods. In 1935, James C. Petrillo, head of the Chicago local of the American Federation of Musicians, initiated the festival, then called Grant Park Concerts, to employ musicians during the Great Depression with funds from the federal Works Progress Administration. Changes in the city's cultural policies, its demographics, financial support, and expectations for how the festival serves the community have impacted how it programs its season and seeks audiences. Based on archival research, this article focuses on how the festival as a civic institution creates a listening public invested in particular narratives of Chicago as a dynamic city through programming music in public spaces. Looking at Grant Park Music Festival from contemporary and historical angles provides insight into how changes in aesthetic and social values, funding for the arts, and urban planning shape the way a festival engages with the city.