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The Journey is the Destination

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I've liked the idea of a train trip going from Chicago through Seattle or Portland, down to San Diego, and back to Chicago for some time. I've never done a train trip aside from the commuter trains from the suburbs into downtown Chicago, so I don't have a realistic sense of what to expect.
I'm wondering about a few things:
1. What is the best way to book with Amtrak (online? by phone? in person?)
2. How should I plan for the connections in the main cities when changing routes (Seattle or Portland, San Fran, San Diego)? If the train is late arriving, how do train connections work compared to airline connections?
3. What should my sightseeing expectations be from the train itself if I do not plan to stop in any of the towns or even cities along the way?
4. Anything else that's important to know about making plans for this trip?

Thanks!

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