Chessie

Chessie may refer to:


 * Chessie (sea monster), a legendary monster supposedly living in Chesapeake Bay, US
 * Chessie System, a former holding company of the Chesapeake and Ohio Railway (C&O)
 * Chessie (mascot), a kitten mascot of the C&O
 * Chessie (train), a proposed streamlined passenger train of the C&O
 * Chessie (band), an American experimental music group started in 1993
 * Chesapeake Bay Retriever, a breed of dog