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There seems to be a bit of debate in some recent threads over which city is more visually recognizable or iconic. To the average person, American or foreign, which city do you think they would have a greater chance of recognizing from photographs? Chicago or San Francisco? You can add up all the iconic locations in each, but it's not a matter of how many, but which ones stick out in people's minds the most.
Going off skylines only, Chicago. Chicago has several instantly recognizable towers-John Hancock, Trump Tower, Willis Tower, to name a few. SF really only has the Transamerica Pyramid to set its skyline apart.
Once you start including street and neighborhood aesthetics, though, it becomes much harder to choose.
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