AmtrakFan said:
Lake Shore Limited New York-Chicago1-2 Night in Chicago
Empire Builder Chicago-Portland
Coast Starlight Portland-Los Angeles
1 Night in LA
Southwest Chief LA-Chicago
4 is very good with OTP so you would be ok
Capital Limtied Chicago-Washington
2 Nights in Washington
Regional Washington-New York
This is a nice itinerary, however, I'd suggest altering it just a bit.
Reverse the start and ending trains. In other words, leave NY and go to DC first, then take the Capitol Limited to Chicao. After doing the west coast legs, upon return to Chicago, take the Lake Shore Limited back to NY.
The reason I'd recommend doing it this way is that it gives you more cushion time to make the connection in Chicago when returning from the west coast. The Capitol leaves CHI at 5:35 pm, whereas the LSL leaves at7:55 pm.
Even though 4 does have a good OTP, I'd still rather have a 4 - 1/2 hour layover, rather than a 2 hour 10 minute layover. That extra cushion time could come in handy if something does delay you on #4.
If 4 does somehow miss the connection with #30, then you'd end up on the LSL anyhow, unless you are really late. So IMHO, avoid the rush, reverse the ends and give yourself more connection time.
And you'll still get dinner on the LSL, assuming that you want to wait until 7:30 or so to eat.