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Expeditionary Forces and Littlehampton, England, to fly missions over the English Channel for the protection of Britain against German Zeppelin airship raids. On June 19, 1912, while in England, Diggins was granted F.A.I. License No. 1719.

After World War I, Diggins returned to Chicago where he founded and became President of the Diggins Aviation Company and School of Aeronautics. He quickly developed this into a sizable business, employing several instructors and using war surplus training planes at Midway Field. This school was in operation until mid-1923, during which time about 400 students were graduated. Many of them went on to become prominent in the aviation industry.

During this period Diggins also pioneered in putting the airplane to work in several useful ways and was credited with making the first air-express flight, from New York to Chicago, in May 1921. Promoting this type of activity, he made numerous flights to distant cities carrying special air express and light freight shipments. He also ferried many notable passengers on business flying trips and did considerable aerial photographic work in the Chicago area.

In 1923 Diggins sold the business to the Mackey Aircraft Company of Forest Park, Illinois. From 1923 to 1925 he was Sales Manager of the Mercantile Finance Corporation of Los Angeles, California, then in 1925 he joined Western Air Express, remaining there until 1927. At that time he became Traffic Manager for Transcontinental Air Transport and served in that capacity until T.A.T. merged with Western Air Express in 1931 to form T.W.A. He then went into business for himself at Los Angeles.

Diggins returned to his former hometown, Harvard, Illinois, in 1934. About 1937 he retired to a dairy farm nearby where he made his home until he passed away at the Harvard Community Hospital on May 13, 1959, at age 72. He was survived by his wife. He was a co-organizer of the National Aeronautic Association, and the Southern California Passenger Association.

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