It began in 1989 as a dream shared by a determined group of Chicago cultural leaders eager to extend the riches of the humanities to all who might benefit – that is, everyone.

Under the aegis of the Illinois Humanities Council and its then-chairman Richard J. Franke, the notion of a "humanities day" was proposed, and then expanded into a "festival." The first Chicago Humanities Festival, a one-day affair, was held on November 11, 1990 at the Art Institute of Chicago and Orchestra Hall, before an audience of 3,500 people. Eight thoughtful yet accessible programs addressed the theme Expressions of Freedom, including a memorable keynote address by playwright Arthur Miller, and inaugurated one of Chicago's most culturally rich annual events. Founding co-sponsor institutions included the Art Institute, the Chicago Symphony Orchestra, Lyric Opera Chicago, and the University of Chicago.

Since that first year, the world's most exciting thinkers have come to Chicago each fall for a Festival celebrating ideas in the context of civic life. Co-sponsored by the city's premiere cultural institutions, each Festival brings together novelists, scholars, musicians, archaeologists, historians, artists, performers, playwrights, theologians, poets, architects, policy makers, and others – both established and emerging talents – to offer presentations around a theme of universal interest, such as Love and Marriage, Crime and Punishment, Work and Play, or New & Old, Peace and War.