Grand Boulevard on the South Side of Chicago, Illinois, is one of the city's Community Areas.

The area is bounded by 39th to the north, 51st Street to the south, Cottage Grove Avenue to the east, and the Chicago, Rock Island & Pacific Railroad tracks to the west.

Grand Boulevard also includes the Washington Park Court District neighborhood that was declared a Chicago Landmark on October 2, 1991.

It arose on the site that from the 1920s through the 1970s housed a famous center of African American cultural life, the Regal Theater.

The Grand Boulevard community area has supported the Democratic Party in the past two presidential elections by overwhelming margins.