Okay, so I"m not sure what the UP is? To be honest, I live by mapquest. So I put my details in and what it told me to do, I did! I just mapquested Toronto to Winnipeg and its telling the exact same route, except I went down through buffalo because I was visiting friends in Niagara Falls. So I went Buffalo to Cleveland and then over to Chicago where as you will cut down through Detroit over to Chicago. The directions its giving me through Chicago are the same I took when I went. You do go through Chicago, I went through at 3am so there was no traffic. As for Minneapolis, there is a ring road that I took, and it was at 4pm in the afternoon and the traffic was fine. As for going up from Chicago, I've done it going from Madison to Milwaukee and then down to Chicago and it does add about an hour, what I did this time was go diagonal from Chicago to Madison. (Mapquest tells you to do this anyways!).
Hope this helps!
Oh and by the way, I did get pulled over just outside of Chicago for going 75 in a 55 zone....but my eyelash batting was in top form and he just told me to slow down! But watch out there because going through Chicago the speed limit is so low and then you get so excited coming out of it that you speed up and there were lots of cops waiting even at 3am. So watch out for that! Also if you cut down through Buffalo the speed limit in Indiana is 70m/h which is awesome! I don't know what it is in Michigan. And when you get to Wisconsin and South Dakota the speed limit is 75! Definitely beats 100km/h going over the great lakes on windy, one-way roads!
Good luck and don't forget to stop in Albertsville just north of Minneapolis for the outlets!
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