Howard Van Doren Shaw was born in Chicago, Illinois on May 7, 1869. His father Theodore was a successful dry goods businessman and was part of the planning committee for the World's Columbian Exposition. His Dutch-American mother Sarah (née Van Doren) was a prolific painter and a member of the Bohemian Club. Howard had one brother, Theodore, Jr. His family resided at 2124 Calumet Avenue, then a part of the Prairie Avenue district, the heart of the social fabric of the city. Prairie Avenue was also the site of Chicago's most modern residential architecture, including Henry Hobson Richardson's John J. Glessner House. Howard Shaw met Frances Wells, his future wife, in the district's Bournique's dancing school on Twenty-Third Street. Wells was the daughter of Moses D. Wells, a prominent wholesale dry goods merchant.