As a Torontonian who travels often to Chicago, I have to admit that TO's skyscapers are still well below Chicago in terms of quality and awesomeness.
You got this "wow" feeling when you're in Chicago. I suspect the city's layout and the distribution of supertalls in Chicago contribute to that feeling. TO has many tall buildings, but they're tightly clustered in a few spots. When you're on street level in Chicago, you can see the supertalls on your right, on your left, etc. Not to mention the quality of the buildings and different architectural styles in Chicago.
TO still has a long way to go for #2, but we're getting there
