I think Toronto can win the games of vibrancy, safety, livability, diversity, etc., but in terms of grandeur and impressiveness, we can never match those of Chicago. People will always be more impressed by downtown Chicago than downtown Toronto, BY FAR. Chicago was a city that was built to be grand with ambition, while Toronto was put together bits and pieces gradually, which means it could be nice and cozy, but will never be grand or beautiful in a coherent manner.
University Ave and Bloor st (only between Jarvis and Avenue Road) are the closest thing to be "grand", but the former is excruciatingly boring with insurance companies and hospitals, not to mention buildings are too short for the width of the street, and the latter is very short. We can only dream of having some of the exquisite buildings in Chicago, while here, we let downtown west be dominate by green glass monotony. We have Jarvis and Spadina which should be show-piece grand streets with beautiful buildings and lively retail, but instead, we seem to be happy with mediocre architecture, with significant numbers of gaps in between, and bad public spaces (it is almost embarrassing that Allan Gardens is of the best green spot in downtown Toronto). Yonge st looks shabby mostly, but even if it were lined with condos like the Five, it will still be largely uninspiring.
We are city that always think very small, and we pretend small projects like Berzcy park or Grange Park will make the city a lot nicer. They won't. Sugar beach is encourage, but it is too small to have any noticeable impact. Even the much applauded Queen's Quay still looks drab to me. And when we design public squares, we simply can't think outside the concrete box plus some trees, as if that's all the possibilities. For example, in NPS, even the benches are concrete, large ones, in addition to concrete EVERYTHING. I remember in Vienna, the seating in front of the museums look like this
It is like our designers deliberately want the city to look boring.
