Chicago Film Critics Association Award for Best Director

Winners

 * 1988 - Robert Zemeckis, Who Framed Roger Rabbit
 * 1989 - Spike Lee, Do the Right Thing
 * 1990 - Martin Scorsese*, Goodfellas
 * 1991 - Jonathan Demme, The Silence of the Lambs
 * 1992 - Robert Altman*, The Player
 * 1993 - Steven Spielberg, Schindler's List
 * 1994 - Quentin Tarantino*, Pulp Fiction
 * 1995 - Oliver Stone, Nixon
 * 1996 - Joel Coen*, Fargo
 * 1997 - Curtis Hanson*, L.A. Confidential
 * 1998 - Terrence Malick*, The Thin Red Line
 * 1999 - Sam Mendes, American Beauty
 * 2000 - Steven Soderbergh, Traffic
 * 2001 - David Lynch*, Mulholland Drive
 * 2002 - Todd Haynes, Far from Heaven
 * 2003 - Peter Jackson, The Lord of the Rings: The Return of the King
 * 2004 - Clint Eastwood, Million Dollar Baby
 * 2005 - David Cronenberg, A History of Violence
 * 2006 - Martin Scorsese, The Departed
 * 2007 - Joel and Ethan Coen, No Country for Old Men
 * 2008 - Danny Boyle, Slumdog Millionaire
 * 2009 - Kathryn Bigelow, The Hurt Locker
 * 2010 - David Fincher*, The Social Network
 * 2011 - Terrence Malick*, The Tree of Life
 * 2012 - Kathryn Bigelow, Zero Dark Thirty
 * 2013 - Steve McQueen*, 12 Years a Slave
 * 2014 - Richard Linklater*, Boyhood
 * 2015 - George Miller*, Mad Max: Fury Road
 * 2016 - Barry Jenkins*, Moonlight
 * 2017 - Christopher Nolan*, Dunkirk
 * 2018 - Alfonso Cuarón, Roma

Most wins

 * 2 - Kathryn Bigelow, Joel Coen, Terrence Malick, Martin Scorsese