Tokyo is certainly impressive, but it's nowhere near as aesthetic. It really felt like Chicago knows that its core is an impressive work of history and collection of art, and has made cultivating it a priority. It's that "City as grand work of art" that really struck me, and that no other city has been able to match.
Tokyo certainly has a lot to offer, including some pretty/impressive architecture. But like most Japanese cities, it dates almost entirely since the '50s, and also like most Japanese cities, unbridled growth has been the top urban development priority until about the last 20 years.
Most of the condos you reference along the waterfront were under construction when I was there last which would have been December 2002. Canada as a whole had a pretty big building boom starting around 2000 and heading through about last summer... Their boom lasted a bit longer than ours because they were reaping the rewards of our $4.50 a gallon gasoline :-)
Oh, and the thing that I like about Toronto isn't so much its downtown core, although that's nice to have, it's more the Victorian neighborhoods and its accessibility relative to its size.
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Tokyo certainly has a lot to offer, including some pretty/impressive architecture. But like most Japanese cities, it dates almost entirely since the '50s, and also like most Japanese cities, unbridled growth has been the top urban development priority until about the last 20 years.
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