I've been to Chicago 3-4 times on business and always had a good time....in the summer. Winters are usually really cold. We have a house 3 hours North of Toronto and love the area....again, in the summer. When we moved from NY to Denver many years ago, we considered Toronto (my Dad was born in Canada) as one of the places too move to. The winter weather and working in a foreign country pushed us to other alternatives but I still make it to Toronto once a year wet we go to our place. Niagara Falls is really beautiful and there is much to do between there and Toronto. Toronto is a pretty short trip and a place worth visiting. The city is clean and very international. We have taken some time and rode bicycles around Toronto Island (?). The hockey Hall of Fame is worth seeing as is the Sky Dome. When you ride an hour or so North of Toronto you get to some very pretty lake country sceneries. My vote would be for Toronto and Niagara Falls!