Mohkínstsis — 1.6 million people at the Foothills of the Rocky Mountains, 400 high-rises, a 300-metre SE to NW climb, over 1000 kilometres of pathways, with 20% of the urban area as parkland.
Upon further review, Toronto has a long ways to go to catch up to Chicago. Chicago has 72 buildings that are at least 550 ft. Toronto only has 23. Toronto's clearly #3 though. Not too shabby!