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If we are talking city proper than I can say Chicago, just because it's downtown is older, more established and feels denser, but at the same time Chicago doesn't really have anything like Mississauga, North York, Hamilton adjacent to it, all of which have their own dense urban areas. Driving down the QEW/Gardener from Hamilton to Scarborough gives the impression of a way bigger place than wrapping from South Bend to North Chicago (which I did about a month ago).
The next closest major city to Chicago is Milwaukee and even then that's almost 100 miles from city hall to city hall.
If we are talking city proper than I can say Chicago, just because it's downtown is older, more established and feels denser, but at the same time Chicago doesn't really have anything like Mississauga, North York, Hamilton adjacent to it, all of which have their own dense urban areas. Driving down the QEW/Gardener from Hamilton to Scarborough gives the impression of a way bigger place than wrapping from South Bend to North Chicago (which I did about a month ago).
The next closest major city to Chicago is Milwaukee and even then that's almost 100 miles from city hall to city hall.
I don't get how people can say that Chicago categorically feels bigger than Toronto.
Here are some of my feelings:
Both cities feel fairly similar in size when approaching.
Toronto's skyline (with many high rises) seems to spread out over a larger area. Toronto has lots of high-rises in the suburbs. Whereas in Chicago there are some but the drop-off from downtown to lower-rise is more dramatic.
Toronto's downtown skyline is somewhat denser and has more of the pin-cushion/microchip look.
Chicago's downtown big city avenues are grander, more mature, and therefore more "big city".
Yonge-Dundas Square, which I am not a big fan of, does scream "big city" to a lot of people. So a plus for Toronto. I know Chicago has The Loop but the Union Station district in the lower part of downtown Toronto is fairly comparable in how bustling it is.
Toronto also has a more active theatre district than Chicago does. Again, I am not personally impressed by the cultural authenticity of what's on offer there, but it's still there. And it's still very vibrant.
Big cities to me have their own personalities that permeate the city. On this, Chicago beats Toronto hands down. But this is true of most any large American city compared to a Canadian one, with only a few exceptions.
If going by MSA's than every city I listed is literally adjacent to Toronto, in addition to Markham, Vaughan, Ajax, Brampton, etc. All have smallish down towns with office buildings, high rise condos, etc, that you wouldn't find in a Chicago "suburb" like Michigan City, Gary, Aurora, Naperville, etc.
I don't get how people can say that Chicago categorically feels bigger than Toronto.
To me, Chicago's core looks considerably bigger and grander. The skyline, the avenues, the department stores, the historic structures, the public spaces, the transit terminals, are on another level. There's just more "stuff" in Chicago, from a much bigger airport, to more freeways/rail lines all over the place, and more sprawl reaching deep into the periphery.
The only way I could see that Toronto looks bigger is if you think that more highrise residentials = bigger city. Toronto, as a metro, is clearly much more oriented towards the commieblock typology.
I feel that cities are typically defined by their cores, not their peripheries, so to me, it isn't really a major factor. Plus that would lead to some weird outcomes. One could argue that Prague and Warsaw feel bigger than, say, London, because Prague and Warsaw have peripheries that are almost totally commieblocks, while London has a very green periphery with basically none. Moscow would look bigger than Tokyo under such a worldview.
To me, Chicago's core looks considerably bigger and grander. The skyline, the avenues, the department stores, the historic structures, the public spaces, the transit terminals, are on another level. There's just more "stuff" in Chicago, from a much bigger airport, to more freeways/rail lines all over the place, and more sprawl reaching deep into the periphery.
The only way I could see that Toronto looks bigger is if you think that more highrise residentials = bigger city. Toronto, as a metro, is clearly much more oriented towards the commieblock typology.
I feel that cities are typically defined by their cores, not their peripheries, so to me, it isn't really a major factor. Plus that would lead to some weird outcomes. One could argue that Prague and Warsaw feel bigger than, say, London, because Prague and Warsaw have peripheries that are almost totally commieblocks, while London has a very green periphery with basically none. Moscow would look bigger than Tokyo under such a worldview.
I can see your point but there is also something to be said for a city that looks like a sea of towers.
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