He soon enrolled at the Academy of Fine Arts, Munich in Germany, under the direction of Angelo Junk, Walter Thor, and Franz von Stuck, who was particularly influential on the painter.
[4] Before World War I escalated, Hennings relocated back to his hometown of Chicago and initially resided at the Fine Arts Building on Michigan Ave, where Louis Grell joined him for a short period before the two moved studios to the famous Tree Studio artist colony in Chicago's North side.
At this time Hennings also joined the artist run Palette and Chisel Academy of Fine Art, and by 1916 had already gained respect in Chicago with a number of awards, including a Gold Medal from the Palette and Chisel Club as well as the Englewood Women's Club prize at the Art Institute of Chicago.
[4] Hennings was not the first to receive such a proposition; Walter Ufer and Victor Higgins had both been approached by Harrison three years earlier, and soon settled permanently in the Southwest.
Although Hennings soon traveled back to Chicago to continue his work as a commercial artist, three years later he moved permanently to Taos.
In particular, the artist was able to travel around the area surrounding Taos freely, painting en plein air subjects of intense natural beauty in remarkable light, none of which would have been possible in Chicago.
[3] Such accolades contributed to Hennings' reputation and, also in 1923, the painter was nominated by Oscar E. Berninghaus and Walter Ufer for membership in the Taos Society of Artists.
[7] During one trip back to Illinois, in 1924, Hennings met Helen Otte, an employee at the Chicago department store Marshall Field's.
The two were married just two years later, on July 20, 1926, and travelled extensively through Europe for 16 months for their honeymoon, visiting Italy, France, Spain, and Morocco.
Hennings also received support from the Public Works of Art Project[10] and the Section of Painting and Sculpture, which commissioned the mural The Chosen Site in a Van Buren, Arkansas, post office.