During this time, Dilworth worked on his poetry. His manuscripts were largely written on Art Institute bulletins. Many of his poems from this time are sonnets, and the themes of his work vary from the natural to the political, with occasional humorous poems. He also wrote about music, as he was heavily involved in the Chicago music scene, performing and attending classical music concerts.
Dilworth published several poems, such as "The Cup of Joy", "Les Sonnets Celestes", and "Ode to Morning", but desired to remain an independent poet rather than a poet-for-profit. He received the most acclaim for a patriotic poem, "Harry Butters".
