The 11th Chicago Film Critics Association Awards, given on 1 March 1999, honored the finest achievements in 1998 filmmaking.

• Best Actor:
  • Ian McKellen - Gods and Monsters
• Best Actress:
  • Cate Blanchett - Elizabeth
• Best Cinematography:
  • The Thin Red Line - John Toll
• Best Director:
  • Terrence Malick - The Thin Red Line
• Best Film:
  • Saving Private Ryan
• Best Foreign Language Film:
  • La vita è bella (Life Is Beautiful), Italy
• Best Score:
  • " The Truman Show" - Burkhard Dallwitz
• Best Screenplay:
  • Shakespeare in Love - Marc Norman and Tom Stoppard
• Best Supporting Actor:
  • Billy Bob Thornton - A Simple Plan
• Best Supporting Actress:
  • Kathy Bates - Primary Colors
• Most Promising Actor:
  • Joseph Fiennes - Shakespeare in Love
• Most Promising Actress:
  • Kimberly Elise - Beloved

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