As the pressure to outperform the railroad mounted, Praeger and Lipsner realized that longer-distance routes were necessary in order to emphasize the advantages of aviation. A start would be a route that would connect the two largest cities in the United States, New York and Chicago. The significant distance and rough terrain between the two cities would give a significant advantage to aircraft over trains.
As with everything in a new system, there was a problem. Lipsner and Praeger picked out conveniently located and inexpensive airfields to create a route. That being said, this route had never been attempted. To test it (and garner public approval) Lipsner sent his two favorite pilots, Max Miller and Eddie Gardner to fly the route for the first time.