I'm a software development professional. I've also spent quite a bit of time in both Hyde Park and University City and have met many students from both Chicago and Penn.
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Originally Posted by Planner15
Access to public transit
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University City wins, by far.
A subway line and streetcars run through University City. You can also walk to 30th Street Station, the main rail hub in Philly, and take the regional (mostly suburban) trains and even Amtrak in any direction.
Hyde Park has only suburban trains which run infrequently and buses.
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Originally Posted by Planner15
Quality of public transit
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Philly wins, although not by that much.
There are only two subway lines in Philly, although the city is smaller than Chicago, so it balances out. Both cities have wide swaths which are not densely populated and served only by buses. The big difference is that Philly has noticeably better regional rail coverage than Chicago.
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Originally Posted by Planner15
Access to computer science jobs
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Honestly, neither city is a true tech hub. Philly is at least a short trip on Amtrak or bus from NYC and DC. Overall, the job market and economy in Chicago are mediocre. Conversely, the City of Philadelphia has atrocious business taxes which drive potential employers away.
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Originally Posted by Planner15
weather
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Philly is noticeably warmer.
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Originally Posted by Planner15
Geek friendly
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Neither city really has a geeky vibe.
In general, I found Penn students to be friendly and welcoming. However, this may be skewed by the ones I've met. A Penn alumnus I know admitted to me that many Penn students are jerks.
The University of Chicago has an intellectual, geeky vibe. However, while some Chicago students are friendly, I've found others to be somewhat cold.
In practice, Philly is probably a better fit socially than Chicago for you. Chicago is socially polarized and you really have to find a subculture to fit into. If your interests are mostly geeky, you're not likely to be welcomed by the Chicago mainstream, which is quite conformist. You may or may not fit in with the hipsters. Hipster culture really has nothing in common with old-school geek culture. In Philly, it's much easier to just be yourself and do your own thing.
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Originally Posted by Planner15
Dating scene (I'm a straight male)
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Both campuses have attractive women.
But when looking at the cities as a whole, Philly is vastly superior in this category for you.
The biggest reason for this is that women in Chicago generally prefer jocks and fraternity types. They also tend to be status conscious and to look for men with money. Women in Chicago also tend to run in close-knit circles which you'll have a very hard time breaking into. In my experience, women in Philly are much friendlier and more approachable.
The Wrigleyville social scene is about as ungeeky as it gets. Many of the other Chicago nightlife districts are only marginally better.
Much of the socializing in Chicago takes place in neighborhoods which are miles from Hyde Park. At Penn, you can walk to places where people socialize.