Chicago to NYC is actually a bit out of reach for night trains (which you should absolutely take and absolutely sleep as a baby on your berth) being 1150 km as

Chicago to NYC is actually a bit out of reach for night trains (which you should absolutely take and absolutely sleep as a baby on your berth) being 1150 km as crow flies. There was a comfortably scheduled night Helsinki to Moscow train which covered 950km, made possible by the fact that Moscow-SPb rail line was built almost a straight line and also quite quick. The terrain between NYC and Chicago is rugged so no such path to be expected. Maybe the Chinese would be able to build a 1000 km elevated track between those two cities and make it all work, though they will prefer to make it an 5h daytime ride and not a nighttrain...