Chester is a young chipmunk and grandson to the Old Man.
Dr. Angler kidnaps Chester before the game begins, and Trevor's quest revolves around rescuing him. In Angler's Fortress, Trevor rescues Chester. Together, they return to Chester's house. Chester wonders where his mother is, though her location and identity are not specified.
He appears several other times during the game:
- After Trevor's wiffle bat is shattered in the Ice Cave, Chester will tell the player that Clyde mentioned a wiffle reforger who resides in a place called Cloud Haven.
- After the initial encounter outside the Ice Cave, Chester will appear in West Port when talking to Thomas. He mentions that he and Clyde have been separated and that Clyde is "doing his own thing."
- Chester appears during the game's finale alongside Winter and the king.