My personal feeling is that this is a red herring. I have often heard of people who visit the US for the first time who have no idea of the size of this country. I read of a woman who planned to see the Statue of Liberty in the morning and then the Niagra Falls in the afternoon, and then see the Grand Canyon, (by car), the next day. I wouldn't be suprised if they simply got off of the plane in New York and thought they could rent a car and drive to Montana and sightsee on the way. Then this guy got tired or realized how much driving was involved and tried to fly the rest of the way from Chicago on his New York to Montana ticket.
but 11 of them, and all in different locations?
Also this would not be an unusual for someone to think who was accustomed to railroad tickets as the main way of getting around.