[suburbanite]

I think the Yonge Street example is actually quite apt since it highlights a great difference between the two cities.

Yonge and Eglinton is one of many secondary high-rise clusters in Toronto, a feature that you don't really see in Chicago due to underlying differences between how the cities grew and developed. Chicago is one of the most centralized cities in terms of high-rise location. Tall buildings are tightly grouped within the core, and finding 20+ stories outside of that area is a rarity. This lends itself to having the massive, diverse skyline the city does.

Toronto is possibly the most de-centralized city in Canada/U.S. in this regards. If you could move all of Toronto's suburban commie blocks and new glass towers together in the core it would probably look more like Sao Paulo or some tertiary Chinese city than anything in the States. There isn't really an analogous location in Chicago for St. Clair, Yonge & Eglinton, North York, Downtown Mississauga, Scarborough City Centre, etc. American cities have never really adopted the suburban high-rise living that the largest immigrant groups to Canada are quite familiar with.