Randolph Street is a street in Chicago. It runs east–west through the Chicago Loop, carrying westbound traffic west from Michigan Avenue across the Chicago River on the Randolph Street Bridge, interchanging with the Kennedy Expressway (I-90/I-94), and continuing west. It serves as the northern boundary of Grant Park and the Chicago Landmark Historic Michigan Boulevard District. Several large theaters, as well as city and state government buildings are on and adjacent to Randolph. Metra's Millennium Station is located under Randolph Street.

The Historic Michigan Boulevard District is a historic district in the Loop community area of Chicago in Cook County, Illinois, United States encompassing Michigan Avenue between 11th or Roosevelt Road, depending on the source, and Randolph Streets and named after the nearby Lake Michigan. It was designated a Chicago Landmark on February 27, 2002. The district includes numerous significant buildings on Michigan Avenue facing Grant Park. In addition, this section of Michigan Avenue includes the point recognized as the end of U.S. Route 66. This district is one of the world's best known one-sided streets rivalling Fifth Avenue in New York City and Edinburgh's Princes Street. It lies immediately south of the Michigan–Wacker Historic District and east of the Loop Retail Historic District.