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  #5001  
Old Posted May 21, 2026, 9:47 PM
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One thing I love about Montreal is the night time lighting. They do it better than any other Canadian city.
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  #5002  
Old Posted May 21, 2026, 11:18 PM
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Originally Posted by MolsonExport View Post
Only bettered by New York City and Chicago, although Toronto may eventually surpass the latter in terms of skyline scale (but probably not in terms of skyline quality).
No doubt, the quality will never compare to skylines that developed largely in the 1920s-'50s. As for scale, Toronto must first build a passel of 400-metre+ towers to compete with Chicago on the upper end. Who knows if that will ever come to pass. On the lower end, it has far more highrises than Chicago, but those are not exciting, just filler. The condo crash took a decade to morph from feverish prediction to reality, and the recovery has been just as sluggish so far. Prices are still too high, imo, and condo sizes and layouts are not what buyers want.
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  #5003  
Old Posted May 21, 2026, 11:52 PM
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Quote:
Originally Posted by Gresto View Post
No doubt, the quality will never compare to skylines that developed largely in the 1920s-'50s. As for scale, Toronto must first build a passel of 400-metre+ towers to compete with Chicago on the upper end. Who knows if that will ever come to pass. On the lower end, it has far more highrises than Chicago, but those are not exciting, just filler. The condo crash took a decade to morph from feverish prediction to reality, and the recovery has been just as sluggish so far. Prices are still too high, imo, and condo sizes and layouts are not what buyers want.
That might be a bit of an overstatement. Chicago only has one building with a roof height over 400m and only two with an official height over 400m. And honestly, I'm not sure Toronto even needs one building over 400m to complete on scale considering it also has the CN tower. I agree it's necessary to have several buildings that are well into supertall territory rather than a bunch that just flirt with it though. Need stuff taller than Concord Sky and even 1 BW to complete with stuff the scale of AON or Hancock - especially since office towers tend to also have larger floor plates giving them greater visual heft than residential stuff at similar heights.
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  #5004  
Old Posted May 22, 2026, 12:36 AM
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I don't think Toronto's too far off from being equal or better than Chicago. I agree, Chicago's classic towers; buildings like Willis, 875 NM, AON, and Marina City and Lake point tower are hard to beat. Toronto's skyline already has more highrises, and will be significantly bigger in a few years. Then it'll be somewhat of an apples to oranges comparison. If Toronto were to build a couple more supertalls, especially if they can get into the 1300-1400 range, they would be the clear winner.
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  #5005  
Old Posted May 22, 2026, 12:58 AM
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There used to be a big size gap between Toronto and Chicago around 2000 but it has really narrowed. They are now in the same ballpark.
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  #5006  
Old Posted May 22, 2026, 1:14 AM
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There used to be a big size gap between Toronto and Chicago around 2000 but it has really narrowed. They are now in the same ballpark.
I vividly remember some of the arguments people had on SSC 20ish years ago. In one of them a guy talked about how completely insane and over-the-top boosterish it was to even suggest Toronto would ever come anywhere close to comparing to Chicago.
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  #5007  
Old Posted May 22, 2026, 3:13 AM
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Toronto will be the 'undisputed' #2 skyline for North America, it's only a matter of when.
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  #5008  
Old Posted May 22, 2026, 4:16 AM
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Love me some Toronto, but it ain't ever going to be Chicago, skyline or otherwise.
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  #5009  
Old Posted May 22, 2026, 4:21 AM
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Love me some Toronto, but it ain't ever going to be Chicago, skyline or otherwise.
Boo-urns.
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  #5010  
Old Posted May 22, 2026, 4:39 AM
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Love me some Toronto, but it ain't ever going to be Chicago, skyline or otherwise.
And Chicago isn't Toronto. Your point being?
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  #5011  
Old Posted May 22, 2026, 5:25 AM
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You're right, Toronto will never be Chicago, they are 2 different cities.
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  #5012  
Old Posted May 22, 2026, 1:34 PM
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Originally Posted by Docere View Post
And Chicago isn't Toronto. Your point being?
Toronto has numbers and is very impressive, but Chicago's list of architecturally important towers and overall look/feel is beyond what Toronto has or likely will have.
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  #5013  
Old Posted May 22, 2026, 1:41 PM
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Originally Posted by Coldrsx View Post
Toronto has numbers and is very impressive, but Chicago's list of architecturally important towers and overall look/feel is beyond what Toronto has or likely will have.
We were all born in the 20th century, have fond memories of the 20th century, and many of us consider the 20th century - particularly the first half - to be aesthetically superior to the century we live in so far.

These views can change, however. I remember reading books written as late as the 1950s where the author commented on how gaudy and cheap the Lower Manhattan skyline was compared to the aristocratic architecture of Old Europe, even though we would now consider Lower Manhattan to be the gold standard for skyscraper architecture anywhere in the world.

I think it's pretty clear that, when you compare the two cities, Chicago is much more of a city defined by the 20th century, and Toronto is much more defined by the 21st century.

In a few decades, people might start getting nostalgic about early 21st century architecture, and Toronto would be the clear favourite then.
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  #5014  
Old Posted May 22, 2026, 1:47 PM
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^fair perspective and comment.
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  #5015  
Old Posted May 22, 2026, 2:46 PM
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  #5016  
Old Posted May 22, 2026, 2:54 PM
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I miss the barge.
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  #5017  
Old Posted May 22, 2026, 3:01 PM
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A couple of Toronto captures via Skycandy on SRC



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  #5018  
Old Posted May 22, 2026, 3:06 PM
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Quote:
Originally Posted by hipster duck View Post

I think it's pretty clear that, when you compare the two cities, Chicago is much more of a city defined by the 20th century, and Toronto is much more defined by the 21st century.

In a few decades, people might start getting nostalgic about early 21st century architecture, and Toronto would be the clear favourite then.
well said. Chicago looks the way it does because it boomed earlier on a scale only exceeded possibly by NYC in North America.

City of Chicago growth
  • 1860 112,172
  • 1870 298,977
  • 1880 503,185
  • 1890 1,099,850
  • 1900 1,698,575
  • 1910 2,185,283
  • 1920 2,701,705
  • 1930 3,376,438

City of Toronto growth
  • 1861 44,821
  • 1871 56,092
  • 1881 86,415
  • 1891 144,023
  • 1901 238,080
  • 1911 381,383
  • 1921 521,893
  • 1931 856,955

Many Canucks don't realize this, but even Buffalo was ahead of Toronto until the 1920s
City of Buffalo growth
  • 1860 81,129
  • 1870 117,714
  • 1880 155,134
  • 1890 255,664
  • 1900 352,387
  • 1910 423,715
  • 1920 506,775
  • 1930 573,076
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  #5019  
Old Posted May 22, 2026, 3:37 PM
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Quote:
Originally Posted by hipster duck View Post
We were all born in the 20th century, have fond memories of the 20th century, and many of us consider the 20th century - particularly the first half - to be aesthetically superior to the century we live in so far.

These views can change, however. I remember reading books written as late as the 1950s where the author commented on how gaudy and cheap the Lower Manhattan skyline was compared to the aristocratic architecture of Old Europe, even though we would now consider Lower Manhattan to be the gold standard for skyscraper architecture anywhere in the world.

I think it's pretty clear that, when you compare the two cities, Chicago is much more of a city defined by the 20th century, and Toronto is much more defined by the 21st century.

In a few decades, people might start getting nostalgic about early 21st century architecture, and Toronto would be the clear favourite then.
We may likely get nostalgic for 21st century architecture at some point, but that wouldn't reduce the impact of those early 20th century skyscrapers. Those OGs will very likely always be seen as special. They also have a solid and stately presence at ground level that, for some odd reason, we has since struggled creating with modern skyscrapers.
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  #5020  
Old Posted May 22, 2026, 4:11 PM
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Interesting stats - thanks for sharing Wigs. Can you imagine if time travel tourism was a thing.. would be far more fascinating to visit Chicago, New York, your home Canadian City in 1900, 1880, etc. than modern times, although people from that era would be even more fascinated to visit the present day cities. If I had to pick just three dates for Victoria I would go with 1845 (a few years after the fort was established to get a sense of the true wilderness of the area), 1858 during the booming gold rush days, and 1913 (just after the huge building boom and yet when all/most of the historic buildings fromt he previous decades would still be in place and cars and horses were on seemingly equal footing.

Back to the present and we get great drone photos of Vancouver from giallo's personal drone, what a time to be alive
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