A small, inch-long, shiny black cricket from the Connecticut countryside, Chester feels close ties to his tree-stump home there, where he chatted with swallows and played his music for “woodchucks and pheasants and ducks and everybody else who lives in the meadow or the brook” (133). Although accidentally displaced from his home, he comes to appreciate his new environment in New York. He’s a kind, gentle soul who cares about his friends and appreciates the kindness of others. He eats Mama Bellini’s fancy fruit and vegetable plates, for example, because he doesn’t want to hurt her feelings. Chester shows courage in his willingness to try new things and embrace different experiences in his new life in New York City, like drinking from a cup and enjoying a Chinese dinner. In addition, Chester reveals his strong moral character when he takes responsibility for eating the $2 bill and starting the newsstand fire.

Chester has exceptional musical talent and loves music. He uses his wings like a violinist to play songs of his own creation and, later, songs that humans enjoy. Chester’s wings aren’t useful for flying, but Chester tells Tucker and Harry that “I prefer music anyhow” (30).