Wow. A lot of perfect information thrown out here. All awesome advise.
The one wrench that I want to throw in this well oiled collection of advise is the following: On your way to Anaheim, you can exit the SWC in Fullerton, transfer to Metrolink and take the train just a couple of stops to Anaheim. You really are a lot closer. I don't know about getting car rentals and lodging, but I know there is a shuttle between Anaheim station and Disney.
Returning home, though, going to LAX is extremely important. If you are ticketed FROM LAX and you don't get on their, they could cancel your whole reservation.
Finally, I don't think anyone mentioned this, but your sleeper ticket is your first class ticket to the lounge area in Chicago. You'll get to sit in a bit more comfortable area, with access to coffee, tea, soda, and chips. You will also be called first for boarding and will get to endure less of a "kindergarten walk" - which is when they line everyone up and play follow the leader to the train. LAX is working on a lounge for sleeper passengers - I don't know if it's done yet or what the status is. If the lounge isn't up and running yet, I think they allow sleeper pax to hang out in a cordoned off area of the Traxx bar. There's a Kindergarten walk there, too.
By the way, I hate to be the one that says this, but here goes. Amtrak is not always a well oiled travelling machine. They do pretty good with what they've got. But they operate on a shoestring budget and their schedule is at the mercy of the private railroad companies who's tracks they ply. Things can happen on Amtrak just like any other transit mode. Be prepared for service disruptions, delays, and just shabby service. I typically try to temper my expectations by planning for the worst, hoping for the best and just loving every minute I'm on board and won't let anyone else change that for me.
Good luck, and please be sure to share with us how your journey goes!
And this is even easier. We get off in Fullerton and take a quick cab ride to Disneyland. No need to catch another train and the cab is under $20.00. Super easy!
Although downstairs is closer to the extra bathrooms (I always travel roomette and for the most part go downstairs to use the restrooms unless it's late night), I do notice it does lessen the view, so since your trip already has one upstairs and one downstairs room booked, maybe leave as is and see how it goes this time. I was surprised that I missed having the view when I was assigned to a downstairs room last year.
I hate eating in the dining car, but do it at least once every trip, especially for breakfast so the room can be made up. I don't like trying to make conversation and the awkward silence is worse, but even though all materials say private room dining is part of the SCA's job, I often feel like it's a bother for them, so the whole dining thing is a little uncomfortable for me. You don't have to have the whole giant meal, either, I often get on right at lunch time and suffer through the dining car for a hamburger, then have the SCA just bring me a baked potato for dinner (and maybe dessert too
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To justify the cost, I just look at it like a road trip...on a train..and the extra cost is what I'd pay for hotels and eating out. I also HATE to fly and only do so when I have to, like to Mexico.
In a couple weeks, though I'm facing the 'never ending train trip' since I need to go to Orlando and since they took that route off years ago, never to return, on the Sunset Limited, I have to go to Albuquerque to get on the Chief, go to Chicago, then to DC, then to Orlando. We will see how that goes! Pretty nervous.
All advice here is good. The most important is you are on train time! you will creep along a lot and stop often and sit there for no apparent reason. You will be way ahead of schedule and then manage to fall way behind. Still, with the proper additude it is super relaxing. Oh yea, please realize the sleepers have very thin walls so be sure and use headphones like you would in coach. I not only bring a fully loaded kindle, bit my Fire for movies downloaded as rentals or purchased off Amazon. I think on my never ending trip I may binge on Downton Abbey. OH! as a first class pasenger, take advatage of the wonderful lounges in Chicago and Los Angeles for any waiting time you might have. Lovely, comfy and free snacks.
