By some metrics , such as quantity of high rises in both the city and inner suburbs , Toronto already has a much more vast and extensive skyline than Chicago, especially when you account for seperate nodes such as Yonge Eglinton, Don Mills, Fairview Mall, Six Points, NYCC
But I dont see how we will ever compete with Chicago when it comes to build quality. We don't have the beaux arts and art deco stock and downtown river that gives Chicago its dramatic beauty. Chicago's skyline is much more neat, orderly and visually appealing, while ours is cluttered with bad trends and "premium" semi-gloss window wall and also the soviet style social housing of the late 60s and early 70s.
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