Walter Whitehead was born in Chicago, Illinois, in 1874. He studied at the Art Institute of Chicago before joining the Howard Pyle School of Art about 1901. While at Pyle's school, Whitehead helped Pyle by managing the art supplies which Pyle sold to his pupils at cost. His duties included not only stocking and dispensing the art supplies but balancing the accounts at the end of the month. Whitehead attended the Chadds Ford summer school in 1902. He later returned to Chicago and eventually taught at the Chicago Academy of Fine Arts.