Hmm... according to www.amtrak.com, you could take the 48 Lakeshore Limited from Chicago (15h35m) to Albany, NY, and then the Adirondak up to Montreal (7h35m, not counting waiting time between trains and the border crossing, which can apparently take up to 2 hours).
It might be quicker to take Amtrak to Buffalo (10 hrs), then Buffalo to Toronto (5 hrs), then Toronto to Montreal on http://www.viarail.ca (4 hrs on the express, 5-6 hrs normal, 8 hrs overnight), but you'd have to check the connecting times to see how long it would really take.
I absolutely love the train -- the clackety clack, the gentle swaying, the big seats, the views, and its Kyoto green factor, but given the same choice, I'd fly or drive :)
Having enjoyed both Canadian ViaRail and Amtrak, for this trip would try to get onto the Canadian side as soon as possible. It will take time but I would go by the Toronto route.
I vote for the Toronto route as well.
I would only add that some MTL-TO trains are "express" and can make the voyage between the two cities in a little over 4 hours.
Oh, and there is no longer overnight service between TO and MTL. They cancelled the Enterprise over a year ago, I believe.
Get in Canada as soon as possible. So take the ten hour train to Buffalo (wawawiwa) and then over to Toronto.
I find it incredibly insane to travel for over 20 hours on a train for the price i'm seeing. Why not fly? It'll be the same price and much much quicker.
I hope you have a deal with the train service or you are coming to Montreal for a while.
If you should happen to be arriving in Toronto on a Friday & can afford to purchase a Via 1 ticket, the express train leaving Toronto in the afternoon is a great way to travel to Mtl. It's considered the party train since the drinks flow freely/frequently & Via 1 class is really comfy & the service is pretty darn good (or at least it was 3 years ago during my last trip).
My wife went to/from NYC using the Montreal-Albany-NYC route and that train is *never* on time, particularly because of delays at the border. It's also very slow, but maybe you don't mind it.
We looked into going to Chicago by rail a couple of years back and the schedule + price both seemed very very very blaaah. - You can easily fly out of O'Hare for about USD $230 - direct flight at that. Or if you won't fly, why not at least drive to Windsor, Ont (across from Detroit, approx. 5-6hr drive from Chicago) and take the train from there? Just a thought.
Unless you suffer acutely from airplane phobia, or that you have a free ride, I will never suggest that you take the train from Chicago to Montreal. So long and totally boring, absolutely nothing to see.
Just a quick check on Expedia confirmed that you could get a better deal on a flight from these two cities than anything by train. Plus it will take you just a couple of hours.!
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