Why would I fly when I could get on a bus at midnight and then wake up in LA at 7AM? When flying, sometimes my time spent in security is literally longer than my time in air. And that's not even taking cost into account, you can do $40-50 round trip on Greyhound vs. ~$140 for a flight.
What are the rules on trains?
Express service between Philly and Chicago would probably require new, dedicated, above-grade track, and would not be competitive with any of airline, automobile, or bus travel for decades. Existing passenger trains in the US (other than the Acela) just can't get from A to B fast enough--or even just arriving at a predictable time!--to be worth the fare.
It is definitely easier to build a self-driving car than fix passenger rail in the US, probably by two orders of magnitude.
Cars are more flexible for more people. Trains travel to and from fixed points on fixed schedules.
For some reason people get all romantic about the idea of train travel but in the 21st century USA it's not going to happen.
We have a very robust infrastructure for cars already in place, and it is pretty dynamic. The infrastructure for trains would have to be built and is a lot more static.
In the US cars are also associated with autonomy and independence. The train can take me from Philly to Chicago and I'm on it's schedule, but with a car I'm on my schedule and I can detour to Cincinnati or Detroit. In the US the needs of the individual for the most part trump the need of the masses.