Well you will enjoy your winter tour my freind, but please take this warning, Toronto and Montreal in a few weeks time will be bitter cold, so cold the snow will not fall, with the wind chill temp can fall below -30C. Dress warm, gloves,hat,long underwear under your cloths, try to avois jeans as offer little protection from the elements. Parka would be good, but a warm jacket with thinsiolate or gortex should be fine.
Things to do, things to do, well I know of Toronto, here is a post that I put up a while back...
Canada Post there are some good ideas in there about Toronto.
I do kno we have a couple Montreal folks here, so I will let them answer you questions on that fantasic city
And as for Chicago, I was planning a trip there a couple months back and asked for some ideas and this is what came back from the family, check this link...
Road Trip
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We are planing to do it in about 2 weeks and havent a clue how we are traveling (road/rail?)
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If you would like an opinion on that, For these places, I would have to say road, and why? the road equals FREEDOM, there is no stopping you whneyou pick a place thats off the beaten trail, no waiting, searching though schedules and what not. North American highways are vast and well maintained ( for the most part) and make an excellent means of travel.
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where we will be staying so any suggestions would be great
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Check these links for beds in the cities you will be in:
Montreal
Toronto
Chicago
Booking it using this service not only guarantee s your bed, but if you have any problems, these folks help ya out.
so I could do with some cloathing advice... I was planning on a good fleece, thermal trousers and top with my normal trousers and a t-shirt or two with a gore-tex jacket... is that enough to keep me toasty? 
Hope you have a good one.
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