I often take Amtrak from NYC to Chicago (and back) and just love it. The trip is about 24 hours each way. Train riders are generally friendly. Someone always has a couple of guitars, so it's fun to play and sing along. The bar car is typically friendly and the food car is generally pretty good eats.
Also, some of the stopovers in small midwest towns are a few hours long so you can get out, stretch your legs, and find a nice quaint diner or something to change things up. I've had nothing by great times on the train. Of course YMMV.