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Do ya'll think we can catch up to New York? Or at least Chicago?

In good lighting (like the one below) or from the right angle, Toronto's 2015 skyline comes neck and neck to Chicago's IMO. But on a normal day, I don't think we're there yet. While the look of a skyline is highly subjective, one measure uses the height of the top x tallest buildings as a comparison. By Toronto's current measure, it doesn't reach that of Chicago's. But when looking at Toronto's under construction and proposed, as a collective, it gets much closer -but still doesn't reach the scale of Chicago's 4 tallest buildings.
Despite them eventually reaching similar heights, I still think the location of where and how the skyscrapers are spread out throughout the city is more important. In Toronto's case, the bulk of the skyline density is found along Yonge and Bay Street with outliers sprawling east and west both by the lake and across the financial district. In the years to come, this will balance out of course, but I'd still say the skyline is anchored on this North-South axis (planning guidelines also influence why it looks this way).
Chicago's concentration of skyscrapers is a little more spaced out with Willis, Aon, Trump, and Hancock anchoring very different sectors of their city with many tall buildings in between. And while running on a north-south axes along Lake Michigan, the Chicago River pushes the skyline westward in a different heading.
All subjective of course but those are just my thoughts.

I had to repost this photo because it is one of the best I've seen:

Source: http://medias.photodeck.com/7dc0bd04-a14d-435d-b2a7-28941201e6e5/14-10-24-0670_xgaplus.jpg

14-10-24-0670_xgaplus.jpg

 
Someone recently took these nice photos from a plane of Toronto from many different angles and wow does it ever illustrate how dense and creative our skyline has become

Courtesy of www.skylinescenes.com

If you go to flickr and search "Toronto Skyline" and order your search by "most recent" Scroll down a tiny bit and youll see them these were uploaded just two days ago

Densecity.JPG
 

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Do ya'll think we can catch up to New York? Or at least Chicago?

I'm in Chicago right now and I think that Toronto is pretty comparable to Chicago. One thing I do notice is that there are not as many really new buildings in the glassy style you see in Toronto. Maybe I'm being biased, but maybe Toronto just seems bigger because it is still growing -- the new growth is eye-catching and the shiny panels seem to cover more space.
 

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