The Chicago Film Critics Association Award for Best Director is an annual award given by the Chicago Film Critics Association.
Winners
1980s
| Year | Winner and nominees | Film |
| 1988 | Robert Zemeckis | Who Framed Roger Rabbit |
| 1989 | Spike Lee | Do the Right Thing |
| Woody Allen | Crimes and Misdemeanors |
| Kenneth Branagh | Henry V |
| Tim Burton | Batman |
| Steven Soderbergh | Sex, Lies, and Videotape |
1990s
| Year | Winner and nominees | Film |
| 1990 | Martin Scorsese | Goodfellas |
| 1991 | Jonathan Demme | The Silence of the Lambs |
| Kenneth Branagh | Peter's Friends |
| Joel Coen | Barton Fink |
| Martha Coolidge | Rambling Rose |
| Terry Gilliam | The Fisher King |
| Spike Lee | Jungle Fever |
| Barry Levinson | Bugsy |
| John Sayles | City of Hope |
| Martin Scorsese | Cape Fear |
| Ridley Scott | Thelma & Louise |
| John Singleton | Boyz n the Hood |
| 1992 | Robert Altman | The Player |
| Clint Eastwood | Unforgiven |
| Neil Jordan | The Crying Game |
| Spike Lee | Malcolm X |
| Quentin Tarantino | Reservoir Dogs |
| 1993 | Steven Spielberg | Schindler's List |
| Robert Altman | Short Cuts |
| Jane Campion | The Piano |
| Andrew Davis | The Fugitive |
| Jonathan Demme | Philadelphia |
| 1994 | Quentin Tarantino | Pulp Fiction |
| Tim Burton | Ed Wood |
| Steve James | Hoop Dreams |
| Krzysztof Kieślowski | Three Colours: Red |
| Robert Zemeckis | Forrest Gump |
| 1995 | Oliver Stone | Nixon |
| Clint Eastwood | The Bridges of Madison County |
| Mike Figgis | Leaving Las Vegas |
| Ron Howard | Apollo 13 |
| Martin Scorsese | Casino |
| 1996 | Joel Coen | Fargo |
| Miloš Forman | The People vs. Larry Flynt |
| Mike Leigh | Secrets & Lies |
| John Sayles | Lone Star |
| Lars von Trier | Breaking the Waves |
| 1997 | Curtis Hanson | L.A. Confidential |
| Paul Thomas Anderson | Boogie Nights |
| James L. Brooks | As Good as It Gets |
| James Cameron | Titanic |
| Atom Egoyan | The Sweet Hereafter |
| Ang Lee | The Ice Storm |
| 1998 | Terrence Malick | The Thin Red Line |
| John Boorman | The General |
| Neil Jordan | The Butcher Boy |
| Steven Spielberg | Saving Private Ryan |
| Peter Weir | The Truman Show |
| 1999 | Sam Mendes | American Beauty |
| Paul Thomas Anderson | Magnolia |
| Spike Jonze | Being John Malkovich |
| Stanley Kubrick | Eyes Wide Shut |
| David Lynch | The Straight Story |
2000s
| Year | Winner and nominees | Film |
| 2000 | Steven Soderbergh | Traffic |
| Darren Aronofsky | Requiem for a Dream |
| Cameron Crowe | Almost Famous |
| Ang Lee | Crouching Tiger, Hidden Dragon |
| Robert Zemeckis | Cast Away |
| 2001 | David Lynch | Mulholland Dr. |
| Robert Altman | Gosford Park |
| Ron Howard | A Beautiful Mind |
| Peter Jackson | The Lord of the Rings: The Fellowship of the Ring |
| Baz Luhrmann | Moulin Rouge! |
| 2002 | Todd Haynes | Far from Heaven |
| Paul Thomas Anderson | Punch-Drunk Love |
| Peter Jackson | The Lord of the Rings: The Two Towers |
| Alexander Payne | About Schmidt |
| Roman Polanski | The Pianist |
| Martin Scorsese | Gangs of New York |
| 2003 | Peter Jackson | The Lord of the Rings: The Return of the King |
| Tim Burton | Big Fish |
| Sofia Coppola | Lost in Translation |
| Clint Eastwood | Mystic River |
| Peter Weir | Master and Commander: The Far Side of the World |
| 2004 | Clint Eastwood | Million Dollar Baby |
| 2005 | David Cronenberg | A History of Violence |
| George Clooney | Good Night, and Good Luck. |
| Peter Jackson | King Kong |
| Ang Lee | Brokeback Mountain |
| Steven Spielberg | Munich |
| 2006 | Martin Scorsese | The Departed |
| Clint Eastwood | Letters from Iwo Jima |
| Stephen Frears | The Queen |
| Paul Greengrass | United 93 |
| Alejandro González Iñárritu | Babel |
| 2007 | Joel Coen and Ethan Coen | No Country for Old Men |
| Paul Thomas Anderson | There Will Be Blood |
| David Fincher | Zodiac |
| Tony Gilroy | Michael Clayton |
| Jason Reitman | Juno |
| 2008 | Danny Boyle | Slumdog Millionaire |
| David Fincher | The Curious Case of Benjamin Button |
| Christopher Nolan | The Dark Knight |
| Andrew Stanton | WALL-E |
| Gus Van Sant | Milk |
| 2009 | Kathryn Bigelow | The Hurt Locker |
| Joel Coen and Ethan Coen | A Serious Man |
| Spike Jonze | Where the Wild Things Are |
| Jason Reitman | Up in the Air |
| Quentin Tarantino | Inglourious Basterds |
2010s
| Year | Winner and nominees | Film |
| 2010 | David Fincher | The Social Network |
| Darren Aronofsky | Black Swan |
| Debra Granik | Winter's Bone |
| Tom Hooper | The King's Speech |
| Christopher Nolan | Inception |
| 2011 | Terrence Malick | The Tree of Life |
| Michel Hazanavicius | The Artist |
| Alexander Payne | The Descendants |
| Nicolas Winding Refn | Drive |
| Martin Scorsese | Hugo |
| 2012 | Kathryn Bigelow | Zero Dark Thirty |
| Ben Affleck | Argo |
| Paul Thomas Anderson | The Master |
| Steven Spielberg | Lincoln |
| Benh Zeitlin | Beasts of the Southern Wild |
| 2013 | Steve McQueen | 12 Years a Slave |
| Joel Coen and Ethan Coen | Inside Llewyn Davis |
| Alfonso Cuarón | Gravity |
| Spike Jonze | Her |
| David O. Russell | American Hustle |
| 2014 | Richard Linklater | Boyhood |
| Wes Anderson | The Grand Budapest Hotel |
| David Fincher | Gone Girl |
| Alejandro G. Iñárritu | Birdman or (The Unexpected Virtue of Ignorance) |
| Christopher Nolan | Interstellar |
| 2015 | George Miller | Mad Max: Fury Road |
| Todd Haynes | Carol |
| Alejandro G. Iñárritu | The Revenant |
| Tom McCarthy | Spotlight |
| Adam McKay | The Big Short |
| 2016 | Barry Jenkins | Moonlight |
| Damien Chazelle | La La Land |
| Pablo Larraín | Jackie |
| Kenneth Lonergan | Manchester by the Sea |
| Chan-wook Park | The Handmaiden |
| 2017 | Christopher Nolan | Dunkirk |
| Guillermo del Toro | The Shape of Water |
| Greta Gerwig | Lady Bird |
| Luca Guadagnino | Call Me by Your Name |
| Jordan Peele | Get Out |
| 2018 | Alfonso Cuarón | Roma |
| Bradley Cooper | A Star Is Born |
| Yorgos Lanthimos | The Favourite |
| Lynne Ramsay | You Were Never Really Here |
| Paul Schrader | First Reformed |
| 2019 | Bong Joon-ho | Parasite |
| Noah Baumbach | Marriage Story |
| Greta Gerwig | Little Women |
| Martin Scorsese | The Irishman |
| Quentin Tarantino | Once Upon a Time in Hollywood |
2020s
| Year | Winner and nominees | Film |
| 2020 | Chloé Zhao | Nomadland |
| Emerald Fennell | Promising Young Woman |
| Spike Lee | Da 5 Bloods |
| Steve McQueen | Lovers Rock |
| Kelly Reichardt | First Cow |
| 2021 | Jane Campion | The Power of the Dog |
| Paul Thomas Anderson | Licorice Pizza |
| Ryusuke Hamaguchi | Drive My Car |
| David Lowery | The Green Knight |
| Steven Spielberg | West Side Story |
| 2022 | Daniel Kwan & Daniel Schinert | Everything Everywhere All at Once |
| Park Chan-wook | Decision to Leave |
| Todd Field | Tár |
| Sarah Polley | Women Talking |
| S. S. Rajamouli | RRR |
| 2023 | Christopher Nolan | Oppenheimer |
| Greta Gerwig | Barbie |
| Todd Haynes | May December |
| Yorgos Lanthimos | Poor Things |
| Martin Scorsese | Killers of the Flower Moon |
| 2024 | RaMell Ross | Nickel Boys |
| Sean Baker | Anora |
| Brady Corbet | The Brutalist |
| Coralie Fargeat | The Substance |
| Jane Schoenbrun | I Saw the TV Glow |
Multiple winners
5 directors have won the award multiple times.
| Wins | Director |
| 2 | Kathryn Bigelow |
| Joel Coen |
| Terrence Malick |
| Martin Scorsese |
| Christopher Nolan |