Dailey was elected assistant city attorney for Peoria in 1894, serving for two years until elected as Peoria County state's attorney. He founded the law firm of Dailey & Miller in 1904 with Harry S. Miller. Also that year, Dailey was elected as Republican to the Illinois House of Representatives, serving a two-year term. Although he did not serve in the next assembly, Dailey was elected to the Illinois Senate in 1908. He served ten consecutive two-year terms. Late in his life, he moved to Chicago.[2]