Dan Ryan Sr. died in 1923 and the board elected Ryan Jr. to fill the remainder of his father's term. From 1926 to 1930, he operated an insurance business before running for the commission in 1930. After his election, Ryan served on the Roads and Bridges Committee and later the Finance Committee. It was in his chairmanship of the Roads and Bridges Committee that he proposed building a superhighway across the city. He aspired to run for Mayor of Chicago as well as Governor of Illinois, however, neither post materialized in his career.