Dill became a lawyer in 1910, and soon entered politics. He was elected to the U.S. House in 1914 and 1916 from the newly created fifth district. On April 5, 1917, Dill was one of 50 representatives who voted against declaring war on Germany. His vote was controversial among his constituents, including members of his own party. The Spokane County Democratic Committee debated censuring Dill, but ultimately voted against doing so. Dill was narrowly defeated for re-election in 1918 by state supreme court justice J. Stanley Webster.