The term Chessie has several meanings including:
- Chessie (sea monster), a legendary monster supposedly living in the Chesapeake Bay, United States
- Chessie System, former holding company of the Chesapeake and Ohio Railway
- Chessie (railroad mascot), kitten mascot of the Chesapeake and Ohio Railway
- Chesapeake Bay Retriever, breed of dog
- Chessie (band), American experimental music group started in 1993