Quote:
Originally Posted by craner
For me the the biggest factor favouring Chicago over Toronto is it’s longest skyline axis is parallel to the lake (Chicago) instead of perpendicular to it (Toronto).
Toronto has, and continues to close the gap rapidly. And I definitely consider the CN tower as an integral part of the skyline.
Chicago is my favourite skyline so I’m likely biased towards it but I can conceive a day that Toronto surpasses it - just hasn’t done so yet IMO. 
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Toronto does not touch Chicago and never will... and Justin Bieber told me to never say never.
Chicago's history, era impact and living legends are way beyond anything that it could touch.