Born in Bristol, England, Bennett attended technical school before immigrating to San Francisco in 1890, where he found work in the architectural offices of Bernard Maybeck. Following Maybeck’s suggestion, he matriculated to the Ecole des Beaux-Arts in Paris from 1895-1902. He moved to New York upon graduating and apprenticed under George B. Post until 1903, when he relocated to Chicago to work with architect and urban planner Daniel H. Burnham. It was with Burnham that Bennett gained acclaim, co-authoring the Plan for San Francisco in 1905 and the Plan of Chicago in 1909. Settled in Chicago, Bennett served on the Chicago Plan Commission and opened a private practice as an architect and city planner, partnering with William E. Parsons and Harry T. Frost. Bennett’s Beaux-Arts education and his involvement with the City Beautiful Movement informed his later city plans, including those for Minneapolis, Detroit, Portland, Oregon, and San Juan, Puerto Rico, among others. His work led the way in establishing zoning ordinances, conducting transportation studies, and designing by regional planning. Bennett served as Chairman of the Board of Architects from 1927-1937, which was responsible for the enlargement of Federal Triangle in Washington, D.C. Bennett retired from practice in 1944.