I just came back from Chicago for the first time and other than geography, I don't see a whole lot of similarities between Chicago and Toronto. Chicago's architecture and downtown is very impressive and grand. Their parks are beautiful and vibrant. Their streets are for the most part well maintained and their sidewalks are large. Toronto has these things as well, but not on such a large scale. But once you venture outside the downtown, it gets really sketchy really fast. There are places I saw in Chicago that were unlike anything I've seen in Canada - people peeing on the streets, whole strips of abandoned stores, and just a lack of life in general. Of course it's not like that everywhere, but I did see some of it. The worst neighbourhood in Toronto in terms of crime would probably be Jane and Finch, and I feel much safer there than I did in some of the places in Chicago. I also went to Gary, Indiana. That was just a depressing place; terrible poverty and urban decay.
I'd be more comfortable comparing NY to Chicago than I would Chicago to Toronto.