Rafi
Conductor
If Toronto and Montreal are options and you're up for a round robin, here's what I'd suggest:
Take the Lake Shore Limited from Chicago to Buffalo, and transfer to the Maple Leaf to Toronto (again, a long layover is the negative aspect here; you could, as jimhudson alludes, take Wolverine 350 to Detroit and get a cab or bus to take you across the border to the Windsor, ON station, but it's not a guaranteed connection and could be a hassle--not sure).
See Toronto for a day or two
Take VIA Rail from Toronto to Montreal, which is a 4.5 hour trip. Montreal is fantastic--I prefer it to Toronto as it really feels like you're in Europe in Old Town. You can also consider a trip up to Quebec City which is supposed to be fantastic as well.
Return to Chicago via the Adirondack connecting to the Lake Shore Limited in Schenectady; the Adirondack is very scenic, to boot, and it's a guaranteed connection to the Lake Shore.
In summary, travel time is:
21 hours to Toronto via Lake Shore/Maple Leaf; 13 hours to Toronto via Wolverine/VIA (on your own to get from Detroit to Windsor; 2 hours 40 mins to make the non-guaranteed connection)
1/2 day between Toronto and Montreal (times vary)
1/3 day between Montreal and Quebec City (times vary; optional side trip--you'd have to backtrack to Montreal to come home)
25 hours from Montreal back to Chicago
-Rafi
Take the Lake Shore Limited from Chicago to Buffalo, and transfer to the Maple Leaf to Toronto (again, a long layover is the negative aspect here; you could, as jimhudson alludes, take Wolverine 350 to Detroit and get a cab or bus to take you across the border to the Windsor, ON station, but it's not a guaranteed connection and could be a hassle--not sure).
See Toronto for a day or two
Take VIA Rail from Toronto to Montreal, which is a 4.5 hour trip. Montreal is fantastic--I prefer it to Toronto as it really feels like you're in Europe in Old Town. You can also consider a trip up to Quebec City which is supposed to be fantastic as well.
Return to Chicago via the Adirondack connecting to the Lake Shore Limited in Schenectady; the Adirondack is very scenic, to boot, and it's a guaranteed connection to the Lake Shore.
In summary, travel time is:
21 hours to Toronto via Lake Shore/Maple Leaf; 13 hours to Toronto via Wolverine/VIA (on your own to get from Detroit to Windsor; 2 hours 40 mins to make the non-guaranteed connection)
1/2 day between Toronto and Montreal (times vary)
1/3 day between Montreal and Quebec City (times vary; optional side trip--you'd have to backtrack to Montreal to come home)
25 hours from Montreal back to Chicago
-Rafi
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