I remain unconvinced these things will ever pay for themselves.
Ask yourself....just how many New Yorkers are begging to go spend a weekend in Chicago? Or how many Chicago folks are begging to go and spend a weekend in New York? It’s a joke. Go and imagine the cost of this round-trip ticket? It’ll have to run at least $300 (my humble opinion).
Now, the positive of this? If you did want to make this trip....you could avoid TSA and the whole airport rountine. You could probably even go and dissolve every single flight between the two cities.
The only corridor where I think there is enough traffic to pay for something like this is NY to Washington. Beyond that....any high-speed rail effort with economic pay-off....is bogus.