2009 - Winners of the 22nd Annual Chicago Film Critics Awards (nominees below in alphabetical order)
| Best Picture |
The Hurt Locker Inglourious Basterds A Serious Man Up in the Air Where the Wild Things Are |
| Best Director |
Kathryn Bigelow (-) The Hurt Locker Joel & Ethan Coen (-) A Serious Man Spike Jonze (-) Where the Wild Things Are Jason Reitman (-) Up in the Air Quentin Tarantino (-) Inglourious Basterds |
| Best Actor |
Jeremy Renner (-) The Hurt Locker Jeff Bridges (-) Crazy Heart George Clooney (-) Up in the Air Matt Damon (-) The Informant! Michael Stuhlbarg (-) A Serious Man |
| Best Actress |
Carey Mulligan (-) An Education Abbie Cornish (-) Bright Star Maya Rudolph (-) Away We Go Gabourey Sidibe (-) Precious: Based on the Novel Push by Sapphire Meryl Streep (-) Julie & Julia |
| Best Supporting Actor |
Christoph Waltz (-) Inglourious Basterds Peter Capaldi (-) In the Loop Woody Harrelson (-) The Messenger Christian McKay (-) Me and Orson Welles Stanley Tucci (-) The Lovely Bones |
| Best Supporting Actress |
Mo'Nique (-) Precious Vera Farmiga (-) Up in the Air Anna Kendrick (-) Up in the Air Julianne Moore (-) A Single Man Natalie Portman (-) Brothers |
| Best Original Screenplay |
The Hurt Locker (-) Mark Boal Away We Go (-) Dave Eggers & Vendela Vida Inglourious Basterds (-) Quentin Tarantino A Serious Man (-) Joel & Ethan Coen Up (-) Bob Peterson |
| Best Adapted Screenplay |
Up in the Air (-) Jason Reitman & Sheldon Turner An Education (-) Nick Hornby In the Loop (-) Jesse Armstrong, Simon Blackwell, Armando Iannucci & Tony Roche The Informant! (-) Scott Z. Burns Where the Wild Things Are (-) Spike Jonze & Dave Eggers |
| Best Foreign Language Film |
The White Ribbon Broken Embraces Red Cliff Sin Nombre Summer Hours |
| Best Documentary |
Anvil! The Story of Anvil Capitalism: A Love Story The Cove Food, Inc. Tyson |
| Best Animated Feature |
Up Coraline Fantastic Mr. Fox Ponyo The Princess and the Frog |
| Best Cinematography |
The Hurt Locker (-) Barry Ackroyd Avatar (-) Mauro Fiore Bright Star (-) Greig Fraser Inglourious Basterds (-) Robert Richardson Where the Wild Things Are (-) Lance Acord |
| Best Original Score |
Up (-) Michael Giacchino Avatar (-) James Horner Fantastic Mr. Fox (-) Alexandre Desplat The Informant! (-) Marvin Hamlisch Where the Wild Things Are (-) Carter Burwell & Karen Orzolek |
| Most Promising Performer |
Carey Mulligan (-) An Education Sharlto Copley (-) District 9 Christian McKay (-) Me and Orson Welles Max Records (-) Where the Wild Things Are Gabourey Sidibe (-) Precious |
| Most Promising Filmmaker |
Neill Blomkamp (-) District 9 Scott Cooper (-) Crazy Heart Cary Fukunaga (-) Sin Nombre Duncan Jones (-) Moon Marc Webb (-) (500) Days of Summer |
2008 - Winners of the 21st Annual Chicago Film Critics Awards (nominees below in alphabetical order)
| Best Picture |
WALL-E The Curious Case of Benjamin Button The Dark Knight Milk Slumdog Millionaire |
| Best Director |
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 |
| Best Actor |
Mickey Rourke - The Wrestler Clint Eastwood - Gran Torino Richard Jenkins - The Visitor Frank Langella - Frost/Nixon Sean Penn - Milk |
| Best Actress |
Anne Hathaway - Rachel Getting Married Sally Hawkins - Happy-Go-Lucky Angelina Jolie - Changeling Melissa Leo - Frozen River Meryl Streep - Doubt |
| Best Supporting Actor |
Heath Ledger - The Dark Knight Robert Downey, Jr. - Tropic Thunder Philip Seymour Hoffman - Doubt Bill Irwin - Rachel Getting Married Michael Shannon - Revolutionary Road |
| Best Supporting Actress |
Kate Winslet -The Reader Amy Adams - Doubt Penelope Cruz - Vicky Cristina Barcelona Viola Davis - Doubt Rosemarie DeWitt - Rachel Getting Married |
| Best Original Screenplay |
WALL*E - Andrew Stanton & Jim Reardon In Bruges - Martin McDonagh Milk - Dustin Lance Black Rachel Getting Married - Jenny Lumet Synecdoche, N.Y. - Charlie Kaufman |
| Best Adapted Screenplay |
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 |
| Best Foreign Language Film |
Let the Right One In The Band’s Visit Che A Christmas Tale I’ve Loved You So Long |
| Best Documentary |
Man On Wire American Teen Dear Zachary IOUSA Standard Operating Procedure |
| Best Animated Feature |
WALL*E Bolt Kung-Fu Panda Tale of Desperaux Waltz with Bashir |
| Best Cinematography |
Slumdog Millionaire - Anthony Dod Mantle Australia - Mandy Walker The Curious Case of Benjamin Button - Claudio Miranda The Dark Knight - Wally Pfister The Fall - Colin Watkinson |
| Best Original Score |
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 |
| Most Promising Performer |
Dev Patel - Slumdog Millionaire Russell Brand - Forgetting Sarah Marshall David Kross - The Reader Lina Leandersson - Let the Right One In Brandon Walters - Australia |
| Most Promising Director |
Tomas Alfredson - Let the Right One In Lance Hammer - Ballast Courtney Hunt - Frozen River Martin McDonagh - In Bruges Steve McQueen - Hunger |
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