Hi, I was wondering if there is a train in windsor that go's to Chicago Illinois?
Amtrak has a train,351 Wolverine, that runs from Detroit,MI to Chicago,IL.
Technically I believe you can take ViaRail to Toronto, then pick up Amtrak into NY and back west through PA, OH, IN. Of course it would be much easier to take a taxi from Windsor to the Amtrak station in Detroit (near Woodward and Grand Blvd). Also look into Megabus - you can get fares as low as $1 if you book far enough in advance. The bus/train trip time is about the same.
Definitely cross the border from Windsor to Detroit and either take Amtrak or the Megabus to Chicago.
I suspect that you already know this, but tev9999 has a good sense of humor in mentioning the "alternative" train route. Technically possible to do, of course, but insanely impractical as it would be about a 16 hour trip from Toronto to Chicago that way. If you took VIA to Toronto, the trip would be even longer. It also would require an overnight stay in Toronto as the first VIA from Windsor (or any other place along the Windsor-Toronto route) gets to Toronto in the morning but well after the scheduled departure of the once a day Amtrak train to Buffalo and points west to Chicago.
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