[wwmiv]

IF Toronto has all of its proposals built (not counting what is already under construction), which is a dubious proposition, I would still put Chicago as having the more impressive skyline for a number of contextual reasons:

A—greater height
B—greater visual concentration
C—better architecture
D—more variation in architecture
E—significantly more skyscrapers underneath this article’s arbitrary boundary - for most people, 150 meters is WAY above the boundary line for what they’d consider a skyscraper... official metrices by cloistered academics be damned - for which points A-D also apply
F—and the fact that, well, Toronto won’t be far enough ahead of Chicago at all at that point on the simple, arbitrary, and totally unjustified metric used by this article (12 towers, or 8% of Chicago’s existing + under construction + proposed tower stock over 150 meters... far less than the difference between NYC and Chicago) for Toronto to say that it unambiguously has a bigger skyline (AKA because it is ambiguous, context matters).

Conclusion: at best Toronto can say it is tied with Chicago.

Also: Toronto’s archetypal tower in the park style is an urban typology of which I am very much not a fan. Skyscrapers often DO NOT equal high quality urbanism. Yay for Toronto, the Miami of Canada.