I've driven London, Ont to Cgy a few times. The quickest way is through Chicago (as long as you don't hit rush hour) and then take I90 (I think that is the one) to Madison Wisconson and from there I took I94 all the way across until you hit Montana. First day starting early, I would end up stopping about Eau Claire Wisc, or Minnisota border. Second day Would get me into Montana. 3rd day gets into Cgy in the afternoon, of course it all depends how hard you want to push; 14 hours with only short meal/fuel stops was my limit. I've found that is around 34 hours driving time.
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