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