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Originally Posted by BuildThemTaller
Eh, that's always been the view of people from Chicago. Truth is that a lot of cities are undergoing a big transformation right now. Look at Austin, Nashville, even Philly and their 30th Street Station redevelopment. Chicago's profile is going to lag behind what's happening because that's sort of how it works.
The first thing that needs to happen for Chicago is to stop losing net population. Once the city population starts to grow again, that's when the national perception - those that haven't been paying attention to what's really happening, at least - will take notice. If the 2030 Census shows population gain for Chicago, for example, expect a bunch of articles with the headline 'Is Chicago the next cool city?' By then, they'll have been behind the curve for more than a decade.
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I'm not originally from Chicago but have lived here a while. I just feel like development and culture wise Chicago is starting to finally turn a corner (which I did not feel originally). I could be wrong though and admittedly am much more attuned to development here than other cities. Population growth isn't spontaneous and takes a nuanced attractive quality work/play/energy environment and so I see many of these developments (plus Riverwalk/Fulton/Ohare etc) all combining into the right formula to spur that.
Austin/Nashville and even Philly are on much smaller scale than Chicago as urban centers but to each his own. I will look more closely at the Philly development you mentioned thank you for pointing that out.