Also, be careful judging prairie cities by their skylines from a distance.
Calgary is the only one that I would consider truly beautiful, at street level. Going from Winnipeg or Saskatoon to Calgary feels like what I imagine it is to cross from Juarez into El Paso.
Take Winnipeg, for example. It's a beautiful enough city from a distance - a nice enough skyline with some very tall buildings.
This is what it's like up close. This was the view from my office for years:
I lived there for 6 years. It TERRIFIES me when people say we should be more like Winnipeg, or Saskatoon, or Regina. It drove me to depression, living in such hideous, car-centric surroundings. I hope we NEVER follow what they're doing, ever.
Calgary even has some areas that look like the above, but they're filling in now because of their oil wealth. Edmonton looks a lot closer to the above than Calgary, but it's still light years beyond Winnipeg, Saskatoon, and Regina.