- Chicago Historical Society Building (Former) 632 N. Dearborn Street · built 1892 · Henry Ives Cobb · designated February 26, 1997 Near North Side
- Chicago Public Library/Cultural Center 78 E. Washington Street · built 1897 · Shepley, Rutan & Coolidge · designated November 15, 1976 Loop
- Civic Opera Building 20 N. Wacker Drive · built 1927-29 · Graham, Anderson, Probst & White · designated February 5, 1998 Loop
- Museum of Science and Industry Palace of Fine Arts, Columbian Museum of Chicago, Field Columbian Museum of Chicago, Field Museum of Natural History, Rosenwald Industrial Museum 57th Street and Lake Shore Drive · built 1891-93 · Charles B. Atwood · designated November 1, 1995 Hyde Park
- South Shore Cultural Center 7059 South Shore Drive · built 1906, 09, 16 · Marshall & Fox · designated May 26, 2004 South Shore
- South Side Community Art Center George A. Seaverns Jr. House, Charles Comiskey House 3831 S. Michigan Avenue · built 1892-93 · L. Gustav Hallberg (1892-93 original building); Hin Bredendieck & Nathan Lerner (1940 interior remodeling) · designated June 16, 1994 Douglas