Shortly after the Post Office gained full control of the airmail service and the route from Washington to New York via Philadelphia, officials began planning their next steps. Second Assistant Otto Praeger announced their intention to create an airmail connection between the nation's two top financial centers, New York and Chicago.Linking New York and Chicago, the nation's major financial centers, would help prove the service's worth to Congress, which held the Post Office Department's purse-strings.But first they had to figure out the best route between the cities.

Praeger and Lipsner, Superintendent of the Airmail Service, chose two of their pilots, Max Miller and Eddie Gardner, for the task of finding the best way over the Allegheny Mountains and to Chicago. The pair left New York on the same day, but in different aircraft. Their goal - make it all the way to Chicago in a single day. Anything less would put airmail on the same timetable as trains, and not worth the money in Congress' opinion.