Yes, I would in a heartbeat, but only if I had a private room with bathroom. My girls and I took Amtrak out in the early 90s from Springfield, MA to Glenwood Springs, CO and back. We loved it. It is such a fun way to see the country and meet people from all over. If you don't want to spend entire nights sleeping through hundreds and hundreds of flat, open plains ala Nebraska, Kansas, etc. you might consider flying into Denver and taking the Zephyr west from there. If you'd like to see the mighty Mississippi River and points west from Chicago, then go from there. The trains from New England to Chicago were terrible, at the time; grimey, worn-out, crowded and uncomfortable. They may have changed since then, though.

We've always wanted to do the Canada one...maybe some time we will. Have fun and if you do come through Colorado, give me a holler.