Ouch!

Pre-TSA I would have said that you might have had a fighting chance to get Amtrak to turn the bag over to your airline and have them fly it out on the next plane possible. But I suspect that's not an alternative anymore with today's security theater.

I quite honestly don't know if they would agree to ship the suitcase to you when it arrives. However, unless the Lake Shore ran really late into Chicago, I have to wonder if your bag simple got put in the baggage area for the Portland section of the train. If that happened, then there is a good chance that they could get it on a Cascades train in the morning and get it up to Seattle possibly before your flight, especially if you go out late in the day.

As for asking for money, since technically the bag isn't declared lost yet, they don't have to give you anything. Even the $100 was above and beyond at this point. I realize that may not help you too much, but there is still the chance that will find the bag for you and send it back to Boston for you to pick up on your return. In that case, they're paying you for something that isn't lost.

Yes, their failure gives you a huge problem, I'm not denying that. But I don't see them going too far in the dollar department until the bag is declared lost.