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| Art Ensemble of Chicago, The (1981) | | | | | | | | | | | |
| At Old Fort Dearborn; or, Chicago in 1812 (1912) | | | | | | | | | | | |
Benaat Chicago (Daughters of Chicago):
Growing Up Arab and Female in Chicago (1996) | | | | | | | | | | | |
| Blues Is Alive and Well and Living in Chicago, The (1970) | | | | | | | | | | | |
| Brooklyn Goes to Chicago (1954) | | | | | | | | | | | |
| Chicago (2002) | |  | | | | | | | | | |
| Chicago 70 (1970) | | | | | | | | | | | |
| Chicago After Dark (1946) | | | | | | | | | | | |
| Chicago Blues (2009) | | | | | | | | | | | |
| Chicago Cab (1998) | | | | | | | | | | | |
| Chicago Calling (1951) | | | | | | | | | | | |
| Chicago Confidential (1957) | | | | | | | | | | | |
| Chicago Deadline (1949) | | | | | | | | | | | |
| Chicago Derby Day (1903) | | | | | | | | | | | |
| Chicago Digest (1952) | | | | | | | | | | | |
| Chicago Fat Stock Parade (1901) | | | | | | | | | | | |
| Chicago Filmmakers on the Chicago River (1998) | | | | | | | | | | | |
| Chicago Fire Boats in Action (1903) | | | | | | | | | | | |
| Chicago Fire Run (1900) | | | | | | | | | | | |
| Chicago Fire Run (1903) | | | | | | | | | | | |
| Chicago Firecats on Parade (1903) | | | | | | | | | | | |
| Chicago Heights (2009) | | | | | | | | | | | |
| Chicago Joe and the Showgirl (1990) | | | | | | | | | | | |
| Chicago Kid, The (1945) | | | | | | | | | | | |
| Chicago Kid, The (1969) | | | | | | | | | | | |
| Chicago Loop (1976) | | | | | | | | | | | |
| Chicago Masquerade (1951) | | | | | | | | | | | |
| Chicago May the Modern Adventuress (1909) | | | | | | | | | | | |
| Chicago Overcoat (2008) | | | | | | | | | | | |
| Chicago Poems (2005) | | | | | | | | | | | |
| Chicago Police Parade (1900) | | | | | | | | | | | |
| Chicago Police Parade (1901) | | | | | | | | | | | |
| Chicago Police Parade (1901) | | | | | | | | | | | |
| Chicago Portland Special (1904) | | | | | | | | | | | |
| Chicago Pulaski Jones (2009) | | | | | | | | | | | |
| Chicago Story (1949) | | | | | | | | | | | |
| Chicago Syndicate (1955) | | | | | | | | | | | |
| Chicago, Chicago (1970) | | | | | | | | | | | |
| Chicago, the Beautiful (1948) | | | | | | | | | | | |
| Chicago-Michigan Football Game (1903) | | | | | | | | | | | |
| Christmas Magic in Chicago (1999) | | | | | | | | | | | |
| Colorado Special, Chicago & Northwestern Ry. (1903) | | | | | | | | | | | |
| Cry Dr. Chicago (1971) | | | | | | | | | | | |
| Don Chicago (1944) | | | | | | | | | | | |
| Duke of Chicago (1949) | | | | | | | | | | | |
| Earl of Chicago, The (1940) | | | | | | | | | | | |
| Fabulous Bastard from Chicago, The (1969) | | | | | | | | | | | |
| Gangs of Chicago (1940) | | | | | | | | | | | |
| Girl from Chicago, The (1932) | | | | | | | | | | | |
| Goin' to Chicago (1991) | | | | | | | | | | | |
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