If you really wanted to go the "when pigs fly" route, one could create a hypothetical LD train that starts in CHI, travels via the Wolverine's route to somewhere near Detroit, crosses the Detroit River, and then runs sealed through Canada until it crosses back over in BUF to go to NYP (using the same tracks as VIA for this segment). I know there used to be a route like this (the Niagara Rainbow), though I figure with the increase in security since 9/11 there's no way this would ever fly with U.S/Canadian Customs today.
In the same vein (though perhaps a bit less "when pigs fly"), I'd like to see a Chicago-Detroit-Toronto train via the Wolverine route and the VIA Corridor. Would essentially operate like the Maple Leaf and the old International - it would operate like a Wolverine in Michigan, but then would essentially become a VIA Corridor train in Windsor. This would be a much better option for going from Chicago (and points west) to Toronto rather than the long connection to the Maple Leaf in BUF or the Detroit-Windsor self-transfer (though you probably couldn't do same-day connections unless you made it an overnight train with sleepers, which would mean ugly boarding times in Michigan).
In a completely different area of the country, I have one more suggestion - an overnight train LAX-EMY via the Coast Starlight's route (though I'd have it extend south to SAN as well). Perhaps just make it a full-fledged second frequency of the Coast Starlight (maybe the Coast Twilight - Coast Daylight doesn't seem like a good name for this). Running overnight would definitely make Amtrak more attractive for this route - as it stands, your choices here are to burn a whole working day on the Coast Starlight (a great train for this, but not very practical time-wise) or take a convoluted combination of buses and trains that involves a similar all-day trip or connections in the middle of the night.
Oh, and extend the Coast Starlight to San Diego on the south end and Vancouver, BC on the north end as well.
Edited by thully, 05 July 2012 - 09:55 PM.