He studied architecture in the Chicago office of the late Charles J. Hull.
He began work as draftsman when he was twenty.
Several years later (in 1889) Mr. Wilson entered into partnership with one of Chicago s early architects, Marble by name, and after his retirement, Mr. Wilson carried on work under the name of Wilson & Marshall. Following the turn of the century he established an independent office, and for a decade was active in the planning and erection of a number of important buildings, including the Illinois Theatre in Chicago, the L. C. Case Office Building in Racine, Wis. (1905), the Sharp Office Building in Kansas City, Mo., and the Railroad Station at Wheaton, Ill., for the Aurora, Elgin & Chicago Railroad. After 1910 he was associated with John A. Armstrong in organizing the firm of H. H. Wilson & Company of which he remained the head until his death.
During that latter period the more important examples of his firm's works were the Macmillan Publishing Company's Office Building and Warehouse in Chicago, erected at Prairie Avenue and 20th Street, completed in 1911, and followed by a large addition to the buildings in 1916. Mr. Wilson also designed the Raymond Apartment House, North Michigan Avenue, and the Surf and Sisson Hotels in Chicago, the latter under construction at the time of Mr. Wilson's death.
Mr. Wilson was a former member of the old Western Association of Architects, and following its merger with the A.I.A. he was advanced to Institute Fellowship.