The Chicago Film Critics Association Award for Best Film is one of the annual awards given by the Chicago Film Critics Association.
| Year | Winner | Director(s) |
|---|---|---|
| 1988 | Mississippi Burning | Alan Parker |
| 1989 | Do the Right Thing | Spike Lee |
| Batman | Tim Burton | |
| Born on the Fourth of July | Oliver Stone | |
| Crimes and Misdemeanors | Woody Allen | |
| Drugstore Cowboy | Gus Van Sant | |
| A Dry White Season | Euzhan Palcy | |
| Henry V | Kenneth Branagh | |
| Sex, Lies, and Videotape | Steven Soderbergh |
| Year | Winner and nominees | Director(s) |
|---|---|---|
| 2020 | Nomadland | Chloé Zhao[3] |
| Da 5 Bloods | Spike Lee | |
| First Cow | Kelly Reichardt | |
| Lovers Rock | Steve McQueen | |
| Promising Young Woman | Emerald Fennell | |
| 2021 | The Power of the Dog | Jane Campion[4] [5] |
| Drive My Car | Ryusuke Hamaguchi | |
| The Green Knight | David Lowery | |
| Licorice Pizza | Paul Thomas Anderson | |
| West Side Story | Steven Spielberg | |
| 2022 | The Banshees of Inisherin | Martin McDonagh[6] |
| Aftersun | Charlotte Wells | |
| Decision to Leave | Park Chan-wook | |
| Everything Everywhere All at Once | Dan Kwan and Daniel Scheinert | |
| Tár | Todd Field | |
| 2023 | Killers of the Flower Moon | Martin Scorsese[7] |
| Barbie | Greta Gerwig | |
| May December | Todd Haynes | |
| Oppenheimer | Christopher Nolan | |
| Poor Things | Yorgos Lanthimos |