The chain operates primarily in Chicago's predominantly black communities but has additional locations in Carbondale, Illinois; Springfield, Illinois; Northwest Indiana; Indianapolis, Indiana; Phoenix, Arizona; Atlanta, Georgia; Las Vegas, Nevada; St. Louis, Missouri; Houston, Texas; Brooklyn Center, Minnesota; and Los Angeles, California.

[2] Harold Pierce, an African-American entrepreneur who moved to Chicago in 1943, founded the restaurant on June 22, 1950, at the corner of 47th Street and Kenwood, near the estate where he worked as a chauffeur.

Some Harold's restaurants are very informal, with takeaway chicken served by employees standing behind a window of bulletproof glass[5] (originally introduced as a necessity rather than an aesthetic concern).

The restaurant is often referenced by Chicago's hip-hop community, including Kanye West, Common, Rhymefest, Juice, G Herbo, Chance the Rapper, Freddie Gibbs, Lupe Fiasco and Dreezy.

[6] Harold's has been shown in a scene on the television show South Side, as well as part of the music video for BJ The Chicago Kid's "It's True".