this is an important observation. chicago has far higher crime, far worse governance, and a worse financial position. but it's also a grand old(ish) city, with great public transit (toronto's is an international humiliation, btw), and just feels a lot more substantial, consequential and wealthy. over the past 20 years, toronto has undergone a construction boom unrivaled anywhere in north america, but chicago still has a lot more buildings and they've a pretty impressive boom there too.
a second point that i think is really important is that americans are just generally a lot more entrepreneurial than canadians. chain shops and restaurants are well-known as being american, but in the cities chains are relatively rare. the sort of formula retail market penetration you have in canada is unheard of until you get to lower tiered cities like omaha or whatever. beyond taxes and regulations and the american spirit, the major reason for the difference in entrepreneurship, imo, is that retail space in canadian cities just costs a lot more than it does in american cities of equivalent mean income. you must have serious resources to open a restaurant in the true north, relative to here. that difference in the percent of small business makes a city like chicago feel psychically different - your neighborhood feels more yours, your downtowns and high streets feel more yours, etc. and over years and decades, that feeling compounds and reinforces the integrity of neighborhoods in a way that is relatively rare in toronto, even in the annex or on the danforth. i have a broader theory about the link between this sort of investment in the community, a broader civic engagement and how that translates into the built form (i guess sort of jacobian) but it's enough here just to say that it's something that i see almost no consideration of in toronto, and it's something that would strike a chicagoan as obviously worth considering.
I think what you point out here, could in many ways be summed up by the 'Canadian way' as I see it. Which is one of compromise and meet-in-the-middle ism. That is neither a knock, nor praise, but rather an observation.
Canadian businesses concede more space to their competitors w/whom they are less fierce on the whole; they in turn, tend to accept a lower profit that might otherwise be possible; but are all but guaranteed a higher profit than might otherwise befall them.
Anyone who grocery shops w/regularly will have seen someone in a suit, not a uniform, wandering the aisles (formerly with a clip board, now usually a tablet) noting prices.
These are staff of the competition. That would rarely, if ever, be tolerated in the US, here.....I see the store manager call that competitor's staff by name and offer to grab them a coffee.
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This approach to doing business or government has its detractions. It tends to result in higher prices, lower rate of innovation, and less promotion by merit. But it also tends to result in fewer dumb risks and lower bankruptcy.
(comm. bankruptcy in recent years tends to be close to 40,000 in the US, but only about 3,000 in CA)
This same effect exists in business regulation which impacts ease of innovation/start-up. Canada, tends to impose higher barriers to entry and compliance on business, benefits/wages, etc. Those are easier to fulfill as a large business than as a new entrant.
I support more innovation and independent business; but I also support thoughtful regulation and labour standards. Striking the best balance is no easy task.
