In a word don't. ICE and Customs on both ends will be going over the truck with 
a fine toothed comb, and can refuse entry for any reason.Moreover the 
trans-Canada route through northwestern Ontario is very sparse. If anything 
happens the tow alone will be expensive. The US route is easier, although the 
Chicago to Minneapolis leg is boring as   white bread.

>Canada route is intriguing...however, I think it might be quite the PITA to
>drive a moving truck across two borders...
>

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