<p>1) UChicago’s reputation is primarily in the field of Economics (and to a lesser extent Physics and Mathematics); Penn’s in is Business and pre-professional studies.</p>
<p>2) Penn is probably better at Art side of Arts & Humanities; Chicago at the Humanities side.</p>
<p>3) Penn has a more diverse total student body (due primarily to size, as its about 2x as large as Chicago), but Chicago won’t be a slouch on this.</p>
<p>4) Based on third-parties, international students at both schools are likely to intergrate themselves in the overall fabric of the school. Chicago will be very moderately more open-minded in a political sense (a result of the conservative intellectual tradition giving a broader breadth of views present and influential at the school) but Penn is probably more socially open minded (for a long time, it was the ‘gay ivy’). For all intents and purposes, they’ll be of similar natures in this regard.</p>
<p>5) Penn will be a little more laid-back overall, but Chicago has normalized itself in this regard (the greek system is rapidly expanding, for example). That said, Chicago>>>Philly in terms of nightlife (though you’ll have to leave HP). </p>
<p>6) Both will be cold in the winter, but Chicago will be colder and windier, with more snow than Philadelphia (though my experience with the two is that Philly gets a lot more rain than Chicago, I haven’t spent all that much time in Philadelphia).</p>
<p>In short: If you get into both, consider this:</p>
<p>You will get to determine much of how your education folds out at Penn, a result of distributional requirements. If you want to devote as much of your time as possible to your field and not need to worry about being told to take certain specific classes/forced to spend more time outside your field, Penn is probably a better choice. If you want to maximize your breadth of study and have a system in place to do that, Chicago is probably the better choice (though at Chicago you still have enough room to concentrate deeply in your chosen field, and at Penn you still have plenty of chance to explore the core of a liberal arts education).</p>
<p>Also, consider your feelings about sports–Chicago has a relatively small sports scene for a college, but the city has a strong professional sports scene. Penn has a stronger on-campus sports scene with a weaker sports city.</p>
<p>In short: Chicago is probably stronger in your interests, but not so much stronger than it’s the clear choice over Penn, which may have more the the personality you want in your college.</p>