The Chesley Awards were presented at Anticipation by ASFA. The Chesleys honor excellence in all forms of art.
- Best Hardback Book Cover: Donato Giancola for A Book of Wizards,
- Best Paperback Book Cover: John Picacio for Fast Forward 2
- Best Magazine Cover: Matts Minnhagen for Clarkesworld, April 2008
- Best Interior Illustration: Donato Giancola for “The Wraith”
- Best Unpublished Color Illustration: Simon Dominic for The Gift
- Best Unpublished Monochrome Work: Simon Dominic for Kraken
- Best Three-Dimensional Artwork: Vincent Villafranca for The Celestial Itinerant
- Best Product Illustration: Dan Dos Santos for Hellboy II promotional art
- Best Gaming Related Illustration: Volkan Baga for Stoic Angel
- Best Art Director: Lou Anders
- Artistic Achievement: Julie Bell
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