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...
We are planing to do it in about 2 weeks and havent a clue how we are traveling (road/rail?)
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.
where we will be staying so any suggestions would be great
Check these links for beds in the cities you will be in:
Booking it using this service not only guarantee s your bed, but if you have any problems, these folks help ya out.