I took MB to Minneapolis this summer, and had a blast. We left at the tail end of Comfest, and I took a nap and woke up in Cincinnati, so I went back to sleep and woke up again at a largish trucker gas station in the middle of nowhere for a break, watching lightening flashing off in the distance in the middle of the night. In early morning in Chicago got right on the bus to Minneapolis, and the day burned on looking out over nice prairie land, and it took a while, but it was nice.
Headed back, we had a 6 hour "layover" in Chicago and the friend I was with was prescient enough to phone a friend before hand, and we had dinner and rode the train around town, and I got to see Wrigley Field out the window. We got back to the stop during a hellacious thunderstorm, and I was having to brush the hailstones off of me like snow, huddled in the wind and cold under the city bus stop. It was an adventure of sorts.
The AC was cranked, so being wet was rather chilly for a while, but it was alright. The WIFI was good, and all the power outlets worked great. I think going out someone had a Festivus pole or something leaning up against the window, and they were asleep and it was driving me nuts rattling loudly on every bump so I moved it slightly.
I think it is a pretty good deal for the money, and even though my phone had died and couldn't look up my reservation number in Chicago, they were able to find a supervisor who looked it up for me. The upper deck is nice to look out and see everything, especially in the front, and the table areas on the lower level of the bus are great if you can get into one. Bring a neck pillow, however, you have slightly more half again as much legroom than an Embraer seat.
I think I would do it again except for the fact that I use twenties to wad up my chewing gum before I throw it away, and for cleaning up little spills around the kitchen.
The site seemed to list the times, and my friend booked hers before me, so my schedule was sort of figured out for me. When I looked at an NYC trip I guess I saw the same thing that it would be a while. I know the quality is less, and the stops are more often, but it seemed like Greyhound had a mostly overnight trip into at least Philadelphia, and arguably you could take a train from there.