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Originally Posted by niwell
This. It's good for events I suppose but most of the time it's kind of a dead zone in the central city - barring the touristy areas around the Bean of course. I go to Chicago fairly often (for fun) and only bothered with Grant Park the first time around.
The Loop has bigger and more impressive buildings than Toronto but also feels more open and airy - Toronto really packs them into a small area. Magnificent Mile is on another level but again I don't really bother going to that area of the city when I visit.
Chicago is "urban" over a far larger area than Toronto, full stop. This shouldn't really be surprising - if we include the metro area it was probably 5x the population in 1945. Effectively 5x the population of Montreal too. Though it's also probably accurate to say that Toronto's "urban" area outside downtown is both more intact and densely built - even compared to nicer areas of Chicago. Commercial streets like Milwaukee are still pretty gappy between El stations.
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On SSP there's often a sort of zero-sum perspective whereby the population in 1945 is used as the baseline for urbanity. In reality of course, a lot has happened over the past 78 years - and many cities have lost urbanity while others have gained. So while Chicago's urban core is still a larger geography than Toronto's in 2023, Toronto's is healthier & more vibrant.
The other factor to consider is that Canada was generally a bit slower to get on the suburban development bandwagon, while development patterns have diverged further in recent years, so "post-war" doesn't mean exactly the same thing. I'd hazard a guess that the proportion of people living in cohesive urban neighbourhoods in Chicago today is maybe 1.5-2x higher than in Toronto now, despite having had 5x the population in 1945.
Also agree re. Grant Park. It looks great from the air, but it's not a particularly human-scaled park at street level, and is bisected by too many wide, fast-moving roads to make for a pleasant environment.