I don't see why Madison doesn't work. I've taken buses to Madison, you can get downtown. You can usually find some transport. Or you can just call a ride share or something!
I've done Chicago -> Madison by bus, and honestly prefer it to the plane at least (even from the airport). More comfortable seats and I get out just at a station. High frequency bus lines feel like good indicators of where some trains could work, and it's not like bus services are dead.
(Similarly, I did Portland -> Eugene on Amtrak and it was nice and chill! I roadshared to my final destination but I had to get from A to B somehow)
I've done Chicago -> Madison by bus, and honestly prefer it to the plane at least (even from the airport). More comfortable seats and I get out just at a station. High frequency bus lines feel like good indicators of where some trains could work, and it's not like bus services are dead.
(Similarly, I did Portland -> Eugene on Amtrak and it was nice and chill! I roadshared to my final destination but I had to get from A to B somehow)