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Originally Posted by niwell
I've been to Chicago over a dozen times and confess I don't really get the fawning over the waterfront. It's fine, but after visiting a few times I didn't see the point of going back - like Toronto the best parts of the city aren't really near the water at all. The best feature is the multi-use path system for cycling but it's also largely separated from neighbourhoods by Lakeshore Drive complete with some pretty uninviting underpasses.
People tend to focus on the brief stretch of Toronto's waterfront redeveloped in the 70s but most of the central portion is in fact publicly accessible (minus the Redpath factory), and the pathway system runs uninterrupted from Mimico to the RC Harris Filtration plant. Plus a massive amount of new public space as the Port Lands begins to come on-line. Gets a lot of flak (some deserved) but actually fairly impressive considering the entirety of the Central Waterfront was reclaimed land intended for industrial uses in the 1920s.
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Chicago's waterfront is undoubtedly grander in that late 19th, early 20th century scale that Canadian cities don't have in significant quantities. It makes a good impression on Google Maps and for someone experiencing the city for the first time visiting the waterfront as a tourist destination. That being said, due to the reasons you mentioned, if I lived in Chicago I doubt I would be walking right along the water very often. Whereas in Toronto, I will happily walk along the boardwalk/Queens Quay to go to a volleyball game at The Docks, to a concert at the Amphitheatre, sit on the patio at Amsterdam Brewery, etc.
I don't have enough experience in Chicago to make such a definitive claim, but my gut feeling is that Chicago's waterfront is a better showpiece, while Toronto's is a more functional interactive place for the people who actually live there. That being said, a historically revisionist dream scenario would include a waterfront showpiece, something like if Coronation Park ran all the way from Ontario Place to Spadina with grand walkways and ornamentation ala Millenium Park. Some will claim that is the void that the Port Lands will fill, and we'll have to wait and see, but I get the feeling that that too will more of a functional space with weekend bicyclists and Cherry Beach goers (which is still a good thing in my mind).