[MonkeyRonin]

Chicago must have the most overrated waterfront of all time. Grant Park looks great from the skyline shots, but at street level is too chopped up by major roads and lacks much of interest - Central Park on the water it ain't. The beachside residential neighbourhoods are better, but are still too cut off from the water by Lakeshore Drive. The best interface with the water is in more peripheral areas like Rogers Park and Evanston. The riverfront is really cool though, and certainly unique. 


Toronto's waterfront has come a long way in being stitched into the fabric of the city, and the actual water's edge is good enough; but given that the central waterfront consists of late 20th-century/early 21st-century development on landfill it will probably always be the core's least interesting neighbourhood. Like Chicago, the peripheral beachfront residential neighbourhoods are better, but it also has the problem of being cut off in the west end by the Gardiner. Its best & most unique waterfront "feature" are probably the islands.