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For what I see, Philly has a much more "blue-collar" "sports-bar" vibe than NYC or even Chicago, and that probably detracts from its hip factor for a lot of people. Folks probably still associate "Rocky" movies with Philly more than almost anything else except maybe music. And the best (popular) music from the city IMO isn't alt rock or something hipsterish like that, but jazz, Hip-Hop, and R&B.
Philly is also physically smaller than NYC or Chicago, so what hipsterdom exists is on a smaller scale geographically, which means that you have to search it out a bit more than you do elsewhere. Not like ChiTown or NYC where there are several larger hard-to-miss neighborhoods that claim to be cool (even if they're not really.)
But all said, Philly isn't nearly as bad as some people make it out to be. (Sort of like Baltimore in that respect IMO). There are interesting neighborhoods, history, lots of students, and yes, all those hipsters who can't afford Brooklyn! It's not Chicago or New York for sure, but looking for cities with a cool urban vibe you could do a lot worse.
I guess it all boils down to what people's individual interpretation of "cool" is. It's a very subjective term. Perhaps the MOST subjective term of all.
Well Chicago and NYC are huge draws as well, NYC from everywhere, Chicago from all around but moreso from the midwestern region. They're the centers of their regions, they're draws, they're huge tourist magnets and financial centers. I've been to Philly and loved it, I want to go back, but I did notice right away that there didn't seem to be the same energy I get in Chicago. Chicago seemed to be more of a magnet sucking in the recent college grads from all over, and NYC is as well. Philly has a lot of that thunder taken away by NYC and DC on either side of it.
i think economy/job market is one of the most important things here, philly doesnt have a great, booming job market that attracts a buncha new people, nyc and chi are much bigger and have much more opportunities, even if their economies are not that great now
I haven't been there yet but based on what I've heard it has the same cool urban city vibe as Chicago/NYC
Your question is vague. Is your question "why is Philly not considered cool AS" (implying equally) , or "cool LIKE" (implying cool too) the cities that you mentioned? If your question is the latter, where and how did you get a consensus that the city it is not considered "cool"? There are plenty of people who think who think Philly is one of the best and "coolest" cities in the US and then there are some people who differ. The same goes the for every large major US city such as NYC, LA etc. Every major city has its lovers and haters. Its all subjective.
In my eyes it would be because NYC and Chicago are at the top of US Cities in terms of awe inspiring and recognition. Philly is much more comparable to Boston, SF, and DC.
To be fair, I'd rather live in Philly over NYC or Chicago. It's the only city that, in my opinion, world-class amenities without the materialism and superficiality that you find in New York, Chicago, LA, SF, DC, and Boston.
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