[jobu]

> you can break the trip up into "daytime travel", stay in a city like Chicago for a few days, and then "overnight" to the next city

My limited experience with Amtrak in the West or Midwest is that it's impossible to reliably plan like this. Amtrak is renting access to rails owned by freight carriers and constantly gets delayed or blocked by freight trains with higher priority.

Their "schedule" is an absolute best-case scenario that never actually happens. The trains usually arrive somewhere between 2-8 hours after the scheduled time, and occasionally it just doesn't show until the next day. They have an app that's supposed to give the "accurate" arrival time is often wildly off as well.

[secabeen]

Chicago is the exception here, though. It's the core hub of the entire system, and there are no trains that pass through Chicago. A Chicago train will nearly always leave on-time, unless there are equipment issues.

[parkingrift]

Similarly in the eastern corridor or at least all the major cities between Boston and Richmond, VA.

Air travel has become such a nightmare that I'd rather take a 7 hour train ride than a 1-2 hour flight.