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 Kieslowski | 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 |
| Milos 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 |
Read more about this topic: Chicago Film Critics Association Award For Best Director, Winners