Son of John Chesshire, of The Oaks, Edgbaston; he studied medicine at Queen's College, Birmingham, and at King's College and University College Hospitals, London. He practised as an ophthalmic surgeon in Birmingham, and was Surgeon to the Birmingham and Midland Eye Hospital. It was largely through his efforts that the hospital was moved from Steelhouse Lane to Temple Row, when after a long interval it was moved to a new building in Church Street. Chesshire practised at 58 Newhall Street, and on retiring lived at The Dingle, Pinner, Middlesex. He died on March 31st, 1903, at Santa Margherita on the Italian Riviera, and was survived by four sons, one of whom died at Folkestone on the same day as his father. A E Chesshire, his son, was an ophthalmic surgeon at Wolverhampton.