[2] While an employee of Robert White, he was encouraged by famous architect Bernard Maybeck to pursue his education in Paris at the École des Beaux-Arts,[2][3] which he attended from 1895 to 1902 thanks to the generosity of Phoebe Apperson Hearst.

He served on the Chicago Plan Commission in various capacities into the 1930s and developed a substantial private practice and a national reputation as a city planner.

From this prototype Bennett developed comparable plans for numerous American cities, including Minneapolis, Detroit, and Portland, Oregon.

[citation needed] Bennett's firm was a pioneer in the creation of zoning ordinances and the study of transportation and regional planning as urban design tools.

His vision of the city was formed in the application of Beaux-Arts design principles of axiality and the incorporation of monumental public buildings as civic markers, coupled with a systematic ordering of functions for efficiency.

Fully three-quarters of the Bennett firm's work done in the 1920s was for official city planning agencies rather than for independent business or civic groups.

Although most of his life's work reflected the Beaux Arts tradition, Bennett also designed two known modernist structures, one a personal studio on the south grounds of the Bagatelle estate, and the other a house in the artist colony of Tryon, North Carolina.

He presented his papers to The Art Institute of Chicago in 1953, and these were supplemented by additional gifts and bequests from his architect son, Edward H. Bennett, Jr., over the following two decades.