| Chicago Film Critics Association Award for Best Supporting Actor | |
| Awarded For: | Best Performance by an Actor in a Supporting Role |
| Country: | United States |
| Image Upright: | 0.7 |
| Year: | Martin Landau (1988) |
| Holder: | Charles Melton May December (2023) |
The Chicago Film Critics Association Award for Best Supporting Actor is an annual award given by the Chicago Film Critics Association.
| Year | Winner and nominees | Film | Role |
|---|---|---|---|
| 1988 | Martin Landau | Abe Karatz | |
| 1989 | Danny Aiello | Do the Right Thing | Sal |
| A Dry White Season | Joe Bella | ||
| Glory | Sergeant Major John Rawlins | ||
| Sea of Love | Det. Sherman Touhey | ||
| Johnny Handsome | Rafe Garrett | ||
| Batman | Jack Napier / The Joker | ||
| Glory | Private Silas Trip |
| Year | Winner and nominees | Film | Role |
|---|---|---|---|
| 2020 | Paul Raci | Sound of Metal | Joe |
| Da 5 Bloods | "Stormin'" Norman Earl Holloway | ||
| Bill Murray | On the Rocks | Felix Keane | |
| Leslie Odom Jr. | One Night in Miami... | Sam Cooke | |
| David Strathairn | Nomadland | David | |
| 2021 | Kodi Smit-McPhee | The Power of the Dog | Peter Gordon |
| Bradley Cooper | Licorice Pizza | Jon Peters | |
| Colman Domingo | Zola | Abegunde “X” Olawale | |
| Mike Faist | West Side Story | Riff | |
| Jeffrey Wright | The French Dispatch | Roebuck Wright | |
| 2022 | Ke Huy Quan | Everything Everywhere All at Once | Waymond Wang |
| Brendan Gleeson | The Banshees of Inisherin | Colm Doherty | |
| Brian Tyree Henry | Causeway | James Aucoin | |
| Barry Keoghan | The Banshees of Inisherin | Dominic Kearney | |
| Mark Rylance | Bones and All | Sully | |
| 2023 | Charles Melton | May December | Joe Yoo |
| Robert Downey Jr. | Oppenheimer | Lewis Strauss | |
| Ryan Gosling | Barbie | Ken | |
| Glenn Howerton | BlackBerry | Jim Balsillie | |
| Mark Ruffalo | Poor Things | Duncan Wedderburn |