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Old 12-21-2015, 07:36 AM
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Many people say that Toronto and Chicago are extremely comparable to each other. When it comes to city population they are roughly the same size, but when it comes to metro, Chicago is significantly bigger. I am curious to hear from people who have been to BOTH, which city feels bigger.

I don't know if it's because Toronto is essentially the NYC of Canada that it seems like it would feel like a bigger city. Another reason is it also seems from photos I have seen of Toronto, since high rises are more widespread throughout the city compared to Chicago where they are confined to downtown and the lakeshore (although that is really starting to change) that it seems like one would think it FEELS like a bigger city.

So which do you feel, FEELS bigger? Or do you they feel the same? Kind of like how Boston and DC feel the same in size.

Old 12-21-2015, 07:56 AM
Location: Washington, DC area
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Been to both many times.

Toronto feels bigger to me, but not by much. Chicago is huge downtown and along the waterfront to the north for many miles, but Chicago quickly becomes very midwestern and sprawly.

Toronto feels huge even out in the suburbs.

I really both cities a lot, two of my favorite cities, but it's pretty amazing just how massive and built up Toronto is considering its population.
Old 12-21-2015, 08:01 AM
Status: "Nobody's right if everybody's wrong" (set 22 days ago)
Location: New Albany, Indiana (Greater Louisville)
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To split hairs Chicago's downtown feels bigger but Toronto's suburbs feel bigger. Toronto has a ton a skyscrapers outside of downtown that make it feel larger when you drive through the suburbs. They have a lot of areas like Atlanta's Buckhead or Midtown where the number of high rises is equal to a mid sized ciy's skyline like Memphis. If you drive around I-294 outside Chicago there are very few tall buildings. But downtown Chicago feels huge.
Old 12-21-2015, 08:05 AM
Location: Atlanta
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Toronto feels bigger to me. When you're driving up the QEW, you feel like you're approaching a very big city by the time you're about 30 miles from it. When I approached Chicago from the south, I didn't quite get that impression until I crossed one of the bridges and then the skyline suddenly appeared, which was magical - I felt like I'd found Oz. Downtown Toronto also seems bigger than downtown Chicago - there's more retail (particularly small independent stores), more streets where you can wander off to and find things of interest, and the main drag (Yonge Street) goes on and on. In any case, two of my favorite cities!
Old 12-21-2015, 09:02 AM
Location: Scottsdale, AZ
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Toronto and Chicago feel similar to me. Downtown Chicago feels bigger, and thats because... it is! Shock! Toronto's burbs felt a bit more urban, but thats about it. There are several suburbs in Chicago that feel urban, too.
Old 12-21-2015, 09:03 AM
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I think Chicago feels bigger than Toronto.
Old 12-21-2015, 09:09 AM
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I have not been to Toronto's suburbs so I can't speak to metro area, but comparing the inner cities/downtown urban areas, Chicago has always felt pretty much larger. Chicago just seems like a huge city (well, it is) in the inner core, I really don't get that sense of scope with Toronto.
Old 12-21-2015, 09:10 AM
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Chicago feels larger than Toronto, IMO. I think there's still a pretty substantial gap.
Old 12-21-2015, 11:59 AM
Location: East Central Pennsylvania/ Chicago for 6yrs.
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Oh no..... not another Chicago vs. Toronto thread But it has been CALM so far. But nobody hold your breath... Both city's were compared in city limit population and both city's hug a Great Lake. With Skyscrapers lining their shores. Another aspect I'd note is..... Both cities have many neighborhoods of single-homes on lots with green-frontage, homes set-back and lack big any substantial Row-Homes.

Chicago has a FULL Alleyway system that are a asset today where most could have garages.... even if it resorted in smaller back yards. But GREAT FOR HIDING its otherwise ugly Power-lines and Poles. and city furnished trash bins stashed there. Creating clean open front green-spaces to front lawns.... once you hit its bungalow belt. Interesting article on the CITY'S EVOLUTION IN HAVING ALLEYS and continued building them till the newest neighborhoods grew to the suburbs alley-less with drive-ways instead to garages in the late 1950s early 1960s last land growth.

Chicago has the largest Alleyway system in the US and more miles of alleys then ANY CITY IN THE WORLD. Chicago has more than 4,000 miles of streets that serve motorists, buses, and 1,900 miles of alleys, providing convenient access to buildings, garages and loading docks.

Curious City: How Chicago became the country's alley capital | WBEZ 91.5 Chicago interesting on what the alleys were originally used for in the oldest neighborhoods. Compared to today. The city also has a GREEN-ALLEY program improving them further.

I am not sure of the level of alleyways Toronto has? But I do see them as a ASSET today and Fronts free from Power-Poles. Makes a BIG difference in street-level vistas. I do know Toronto can have Power-line Poles in fronts of homes in neighborhoods. So I say Chicago has that asset over Most North American cities......

Neighborhoods street-grid have MOST home own owners
could build garages in back and they did...

Chicago is also a very green-space city as I saw much of Toronto is.
TREES are many times HIGHER then Rooftops.

Old 12-21-2015, 12:34 PM
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I'd say it's kind of a draw overall, but depending on whereabouts you look in each city, one feels bigger than the other.

For example, Chicago's Loop feels bigger then Toronto's financial district, and the Magnificent Mile feels bigger than Toronto's Bloor-Yorkville, but Yonge-Dundas Square and the Yonge Street strip in Toronto has an urban assault on the senses and a critical mass that you don't really find in Chicago.

Toronto also feels bigger than Chicago outside the downtown core and in the suburbs due to all the high density nodes of development (hi-rises everywhere!) and transit use. Chicago doesn't have anything on the scale of Yonge-Eglinton and North York Centre within its city limits the way Toronto does, or anything as massive as Mississauga City Centre in the suburbs.
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