I know the problem you're facing - connections between Canada and Chicago are pesky - the whole direction ('clockwise' instead of 'anti-clockwise' - see
jamesbrownontherails.blogspot.com) of my N. America Rail Pass trip has been influenced by the fact that Amtrak can make a connection Montréal to Chicago, but not Chicago to Montréal... :blink:
So, while the Greyhound might be the most sensible option, here are two possible alternatives... maybe not what you were expecting....!
1) This is the expensive option, unless you can find good last minute deals on rooms. It's good if you 1) really don't like the idea of spending seven hours in Buffalo 2) don't fancy spoiling your rail trip with a leg on Greyhound bus
and 3) want to get the most out of your railpass. Travel Chicago - New York (by the 'Cardinal' perhaps to add some variety of scenery?) spend the night there and then take 'The Maple Leaf' to Niagara Falls the next day. Spend the night and the leave on the 0645 (Mon-Fri) / 1410 (Sat-Sun) VIA train to Toronto. Both would allow you to connect to Montréal (arriving in Montréal at 1426 or 2355 respectively). So you have two nights of accomodation to find in New York and Niagara Falls, ON, but not Toronto.
2) .... or go to Niagara Falls on your return instead. Travel via Buffalo to Toronto and take it easy in Buffalo for lunch and maybe visit a gallery (the Albright-Knox Art Gallery is a stunning collection: I could personally pass seven hours quite happily there....). Catch the Maple Leaf through to Toronto, stay overnight, then continue your trip Montréal - Québec - Halifax - Montréal - Toronto. Then take the Maple Leaf to Niagara Falls, ON and spend the night there before leaving the next morning. That means hotels needed in Toronto and Niagara Falls.
So, certainly a difficult one re: accomodation. Your solution may well be the best, but I admit it would feel a bit of a let down to have to resort to the 'hound. But, it's not yet high season, and you're booking late, so you might find a good last minute deal. Have you tried
priceline.com - start your bidding at 25% - 30% below the lowest rate you can find elsewhere and see what you get. I always find planning Rail Pass trips throws common sense out of the window. It's not usually a matter of 'do I want to go there' but 'ooo.... I can go there... let's do that instead'....
Enjoy the trip.... if you need any inside tips for Montréal, drop me a line. I'm no good on hotels (although we do have a couch) but everything else I should be able to help :blink:
Happy travelling,
*j*