The 21st Chicago Film Critics Association Awards, given by the CFCA on December 18, 2008, honored the best in film for 2008. Disney/Pixar's WALL-E was the most successful film in the ceremony, winning four awards, including Best Film, out of five nominations. Slumdog Millionaire won three awards, while The Dark Knight and Let the Right One In won two awards each.

Mickey Rourke – The Wrestler

• Clint Eastwood – Gran Torino
• Richard Jenkins – The Visitor
• Frank Langella – Frost/Nixon
• Sean Penn – Milk

Anne Hathaway – Rachel Getting Married

• Sally Hawkins – Happy-Go-Lucky
• Angelina Jolie – Changeling
• Melissa Leo – Frozen River
• Meryl Streep – Doubt

WALL-E

• Bolt
• Kung Fu Panda
• The Tale of Despereaux
• Waltz with Bashir

The Dark Knight – Wally Pfister

• Australia – Mandy Walker
• The Curious Case of Benjamin Button – Claudio Miranda
• The Fall – Colin Watkinson
• Slumdog Millionaire – Anthony Dod Mantle

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

Man on Wire

• American Teen
• Dear Zachary: A Letter to a Son About His Father
• I.O.U.S.A.
• Standard Operating Procedure

WALL-E

• The Curious Case of Benjamin Button
• The Dark Knight
• Milk
• Slumdog Millionaire

Let the Right One In (Låt den rätte komma in), Sweden

• The Band's Visit (Bikur Ha-Tizmoret), Israel
• Che, France, Spain, & USA
• A Christmas Tale (Un conte de Noël), France
• I've Loved You So Long (Il y a longtemps que je t'aime), France

WALL-E – Thomas Newman

• The Curious Case of Benjamin Button – Alexandre Desplat
• The Dark Knight – Hans Zimmer and James Newton Howard
• Milk – Danny Elfman
• Slumdog Millionaire – A. R. Rahman

Slumdog Millionaire – Simon Beaufoy

• The Curious Case of Benjamin Button – Eric Roth
• The Dark Knight – Jonathan Nolan and Christopher Nolan
• Doubt – John Patrick Shanley
• Frost/Nixon – Peter Morgan

WALL-E – Andrew Stanton and Jim Reardon

• In Bruges – Martin McDonagh
• Milk – Dustin Lance Black
• Rachel Getting Married – Jenny Lumet
• Synecdoche, New York – Charlie Kaufman

Heath Ledger – The Dark Knight (posthumously)

• Robert Downey Jr. – Tropic Thunder
• Philip Seymour Hoffman – Doubt
• Bill Irwin – Rachel Getting Married
• Michael Shannon – Revolutionary Road

Kate Winslet – The Reader

• Amy Adams – Doubt
• Penélope Cruz – Vicky Cristina Barcelona
• Viola Davis – Doubt
• Rosemarie DeWitt – Rachel Getting Married

Tomas Alfredson – Let the Right One In (Låt den rätte komma in)

• Lance Hammer – Ballast
• Courtney Hunt – Frozen River
• Martin McDonagh – In Bruges
• Steve McQueen – Hunger

Dev Patel – Slumdog Millionaire

• Russell Brand – Forgetting Sarah Marshall
• David Kross – The Reader
• Lina Leandersson – Let the Right One In (Låt den rätte komma in)
• Brandon Walters – Australia

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