In 1929 Bowles joined forces with his friend, William Benton, to establish an advertising agency, Benton & Bowles. The business was a great success and their clients included Proctor & Gamble and Maxwell House. By 1935 the Benton and Bowles agency was the sixth-largest advertising firm in the world.
After Pearl Harbor Bowles attempted to join the U.S. Navy. He failed his medical and was offered the post as director of the Office of Price Administration in Connecticut. In 1943 President Franklin D. Roosevelt appointed him as general manager of the Federal Price Administration.
In 1946 President Harry Truman appointed him as director of the Office of Economic Stability. He also published the book, Tomorrow Without Fear (1946). Bowles also worked for the UN Appeal for Children in Europe before being elected as Governor of Connecticut in 1949. At the end of his term Truman appointed him as ambassador to India.
A member of the Democratic Party, Bowles was elected to the Eighty-sixth Congress (January, 1959-January, 1961). President John F. Kennedy appointed Bowles as his Undersecretary of State. He was highly critical of Kennedy's decision to go ahead with the Bay of Pigs operation. Bowles once again became ambassador to India (1963-1969).
Bowles wrote several books including Africa's Challenge to America (1956), Ideas, People and Peace (1958), The Makings of a Just Society (1963), A View From New Delhi: Selected Speeches and Writings (1969), Promises to Keep: My Years in Public Life (1971), Ideas, People and Peace (1974) and Conscience of a Liberal: Selected Writings and Speeches (1975).
Chester Bowles died in Essex, Connecticut, on 25th May, 1986.