Multiple winners
5 directors have won the award multiple times.
| Wins | Director |
|---|---|
| 2 |  Kathryn Bigelow |
| Joel Coen | |
| Terrence Malick | |
| Martin Scorsese | |
 / Christopher Nolan |
The Chicago Film Critics Association Award for Best Director is an annual award given by the Chicago Film Critics Association.
| 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 |
5 directors have won the award multiple times.
| Wins | Director |
|---|---|
| 2 | Kathryn Bigelow |
| Joel Coen | |
| Terrence Malick | |
| Martin Scorsese | |
| / Christopher Nolan |
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