Chicago Film Critics Association Award untuk Skenario Terbaik adalah salah satu penghargaan tahunan yang diberikan oleh Chicago Film Critics Association.

• 1990: Goodfellas – Nicholas Pileggi dan Martin Scorsese
• 1993: Schindler's List – Steven Zaillian
• 1994: Pulp Fiction – Roger Avary and Quentin Tarantino
• 1995: The Usual Suspects – Christopher McQuarrie
• 1996: Fargo – Joel Coen and Ethan Coen
• 1997: L.A. Confidential – Curtis Hanson dan Brian Helgeland
• 1998: Shakespeare in Love – Marc Norman dan Tom Stoppard
  • Bulworth – Warren Beatty dan Jeremy Pikser
  • Happiness – Todd Solondz
  • A Simple Plan – Scott Smith
  • The Truman Show – Andrew Niccol
• 1999: Being John Malkovich – Charlie Kaufman
  • American Beauty – Alan Ball
  • Magnolia – Paul Thomas Anderson
  • The Sixth Sense – M. Night Shyamalan
  • Topsy-Turvy – Mike Leigh

• 2000: Almost Famous – Cameron Crowe
  • State and Main – David Mamet
  • Traffic – Stephen Gaghan
  • Wonder Boys – Steve Kloves
  • You Can Count On Me – Kenneth Lonergan
• 2001: Memento – Christopher Nolan
  • A Beautiful Mind – Akiva Goldsman
  • Ghost World – Daniel Clowes dan Terry Zwigoff
  • Gosford Park – Julian Fellowes
  • The Royal Tenenbaums – Wes Anderson dan Owen Wilson
• 2002: Adaptation. – Charlie dan Donald Kaufman
  • About a Boy – Peter Hedges, Chris Weitz, dan Paul Weitz
  • About Schmidt – Alexander Payne dan Jim Taylor
  • Far from Heaven – Todd Haynes
  • Punch-Drunk Love – Paul Thomas Anderson
• 2003: Lost in Translation – Sofia Coppola
• 2004: Sideways – Alexander Payne dan Jim Taylor
• 2005: Crash – Paul Haggis dan Bobby Moresco
  • Brokeback Mountain – Larry McMurtry dan Diana Ossana
  • Capote – Dan Futterman
  • Good Night, and Good Luck. – George Clooney dan Grant Heslov
  • A History of Violence – Josh Olson

• [1] Diarsipkan 2015-08-22 di Wayback Machine.
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