Hubby and I have a trip coming up in May: Southwest Chief from Los Angeles to Chicago, Lakeshore Ltd from Chicago to Boston, Downeaster from Boston to Portland ME where we will rent a car and drive to Bar Harbor. Then the entire trip in reverse. Not only did it cost me well over $5K for train fare (bedrooms) but I am absolutely staggered at the cost for hotels, and we stay at decent but not fancy places. The trip, which is 18 days total with 11 nights total in hotels, is costing a fortune and I don't think we'll do such a long trip with multiple legs and hotels again.
First, be sure you have notification status with amtrak.com/deals. There’s a good chance that soon (before May) that as happened last year, Amtrak will offer a substantial discount, even if you were already booked - shaved off 25%!
Coach hybrid? You can perhaps go coach for part of your trip maybe the return LSL might be a good choice. Especially since LSL doesn’t currently have traditional dining. I think you’ll still be able to use the metropolitan lounge in Chicago - the showers are great by the way
Getting into Boston if you’re not familiar with the Back Bay, ask the conductor as you get off which way to the orange line that brings you to North Station and of course the DownEaster. But if you decide to go into South Station instead, I would recommend a cab too BON because they’re the same price as an Uber or Lyft driver PLUS there’s a Taxi stand at BOS.
In Portland, there is a full fledged Marriott AND A variant Marriott called “Aloft” hotel. The cabbie was confused until he saw the cryptic Aloft sign on the building. Both Marriott’s are on Commercial Street - Portland’s main drag. The great restaurant is across from Aloft is Becky’s Diner - if you like outside ask for the upstairs porch with harbor view.
The Aloft was about $90, includes breakfast. Young crowd, as is Portland. I was on the 6th floor and the bed faced this huge window - facing the city’s beautiful architecture in the morning light! They slored my bag after checkout so I could take a brief round trip on a ferry. I recommend the “Aloft.”
I would maybe have the car delivered to the actual AMTRAK Portland station rather than the hotel - it cost me $25 to get from the Portland station to the hotel and it was only a few miles.
LASTLY - What a great trip you’ll have to Bah Hah-bah. All the nooks and crannies of the Maine Coast coming into bloom.