Sorry to have annoyed you! I find comparisons to Chicago equally annoying.
And since the cities aren't considered by anyone except people on this forum to be the same size, coming up with = areas seems like an arbitrary way to compare - it's like trying to find a way to say that Toronto, somehow, is the same size as Chicago, even if it turns out we are pretending that all of Ontario is part of Toronto. (Ontario's GDP is essentially equal to Chicago's.) Sure, if that makes you feel good, but I don't think it comes close to reflecting reality.
And my point is that this sort of "Toronto is the same as Chicago! Therefore we should have equal things!" idea is the sort of chant we hear from people who think that we need to be globally important and that all cities follow the same trajectory in their development. Toronto is veeeeeeerrrry different from Chicago, its history is enormously different, and in the context of American power, it is rising, but still nowhere as important. But that's okay! Toronto has to find its own way, and not pretend that Chicago is some marker of development.