Robert Boyle Chillingworth was born at 1 Audley Place, Cork, Co. Cork, Ireland on 28 July 1878 and studied at the School of Engineering, Queen's College, Cork from 1897 to 1902. He then worked briefly as an assistant to the Cork architect and engineer Henry William Hill (1867-1941) on the construction of the Cork & Muskerry Light Railway, and from 1903 to 1905 was employed as an assistant in the office of W/. H. Hill & Son in Cork.
While working at W. H. & Son, Chillingworth met Daniel Andrew Levie (1875-1963) and together they formed the architectural partnership Chillingworth & Levie in Cork in c.1911.
Chillingworth's architectural career was short-lived as in 1916 he fell victim to tuberculosis and died at his home, Woodville in Rochestown, Co. Cork on 3 December 1916.
Works by Chillingworth: a house for his brother, J. Chillingworth, Carrickbrack Road, Dublin (1911-12). Work by Chillingworth & Levie during Chillingworth's time as a partner: alterations to the Methodist Church, Dunmanway, Co. Cork (1912); a housing scheme for Youghal Urban District Council, Co. Cork (1912); working men's housing scheme, Youghal, Co. Cork, (1914); shop front, car showroom for Johnson & Perrott Ltd, Winthrop Street, Cork (c.1915).