Hi Shannon.
The caricature artists working around Walt Disney World's parks and resorts are very talented!
They are contracted to work at about a dozen locations at WDW through an outside company and there are usually more than 40 of them on rotation at any given time.
There is usually an artist in Hollywood Studios daily. Check the Daily Times Guide or inquire at HS Gust Services as you enter the park for the artist's schedule and location.
The artists themselves will have great experience with the likenesses of most familiar Disney Characters, but none would necessarily 'specialize' in Star Wars characters. Your best bet would be to approach any that you see, and let them know what you'd like to do. They'll be able to advise you best on what they are able to do for you.
You'll find caricature artists located in all four parks as well as at Downtown Disney and in the lobbies of Disney's Wilderness Lodge, Beach Club and Contemporary Resorts. Current pricing ranges from approximately $20-$60 for one subject and vary depending on color, characters and background added. The Caricature Artist you speak with will best be able to quote on your idea for you.
You may also consider a visit to
Tatooine Traders for great, unique Star Wars gift ideas. The shop is located adjacent to
Star Tours - The Adventures Continue in Disney's Hollywood Studios.
Thanks for visiting the Moms Panel with your question Shannon.
Wishing you a simply Magical time at Walt Disney World!
Kirsten