 Post, who sent him to Chicago to assist architect Daniel H. Burnham in preparing a plan for the military academy at West Point.Burnham found Bennett's work highly satisfactory and in 1903 invited him to move to Chicago to collaborate on the comprehensive plan for San Francisco, and afterwards, the Plan of Chicago.The completed San Francisco plan was not implemented in the aftermath of the 1906 earthquake, but Bennett became well known for his design work and co-authorship of the 1909 Plan of Chicago.