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Sometimes cheaper than flying if you get a regular fare. Sleeping cars make it non-competitive w/flying - depending upon where you're going. Have used it on short hops too = San Diego-LA growing up in SD; and now Chicago-St. Joseph, MI and Chicago-Milwaukee.
Long distance I've ridden Chicago - Santa Fe, NM (Lamy) twice (about 24 hours) and Chicago - Tucson once about 48 hours (you hook up with the Orlando-LA train in Texas). Tucson and latest Santa Fe trip with the kids. Trips do take some time, but I used them to bracket and extend business trips. 24 hours is better than 48, but as you don't sleep much the first night, the second night's sleep is better. Bring soft earplugs, as it seems it isn't the rocking but the noise that keeps you awake.
Being in a sleeping car gets you free meals in the dining car. The experience isn't fancy, but it is pleasant. I have a cramped, coach-class trip to Japan coming up, and I much prefer to get up and walk around and talk. No cellphones or emails for a day or two helps my stress level before and after a business trip too. If you like to drive cross-country, you'll probably enjoy the train - it is quicker than driving since you don't have to stop at night, but still has that pleasant "free time" feel. If you can't stand cross-country driving, you won't like it.
You have to have a romantic streak in you, and enjoy pointless Sunday drives and other adventure journeys, or the realities will bother you: It can be slow, and is usually a bit late arriving.
If you're in a hurry, you shouldn't be on a piece of 19th Century technology to go across a continent - wheather it is a train or a car.
Heard the best trains for sights are Chicago-SF (Rockies & Sierras) and Chicago-Seattle (Glacier N.P.)
Chicago to Santa Fe runs on the same rails my commuter train does, and it was really kind of fun, though the scenery isn't much until you get out to the Colorado/New Mexico border.
Scenery in Texas was great - to watch in one day as the swampy east gave way to rolling hills and then to the dry west. Made me think about buying some land!
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