<p>Some quick, sleepless impressions:</p>
<p>There are certainly intellectual undergraduates at Penn, but that's not the character of the place, and the ones I have known have felt somewhat embattled, part of a secret subculture. To some extent, if you are that kind of person, it makes it easier to get faculty attention, etc., at Penn compared to Chicago, where everyone is more or less like that, but you won't feel like you are surrounded by your tribe. On the other hand, if you are NOT that kind of person, at Penn you won't feel like you are surrounded by pretentious eggheads. Remember, a third of Penn undergraduates are in Wharton, and there are also engineers, nursing students, etc. That gives Penn a much, much more practical, careerist spirit than Chicago. That isn't to say that everyone isn't smart -- everyone is smart, but everyone doesn't want to get a PhD. If one of Chicago's mottoes is "That's fine in practice, but how does it work in theory?", Penn's equivalent could be "Screw theory."</p>
<p>Chicago has its Core Curriculum, which gives all undergraduates a fairly extensive set of common reference points, whatever their interests, and also occupies up to a third of their college time. Penn has nothing like that.</p>
<p>Penn is actually much more urban than Chicago. Hyde Park is a sleepy little enclave 6-7 miles from the downtown Loop area, and even farther from the hip neighborhoods where young people hang out. Penn is basically adjacent to Center City Philadelphia -- walking distance or a 5 minute subway ride away from the action. Big streets run through it, many of the dorms are high-rises, most of the buildings modern, fancy restaurants and upscale retail stores dot the campus. There are a few placid nooks and crannies, but you are never far from traffic and bustle. Not true at Chicago.</p>
<p>Chicago (the city) is much larger, richer, more vibrant than Philadelphia. There's more to do there, and it costs a lot more to do it. No one really needs to cater to students. Philadelphia is probably more student-oriented.</p>
<p>Penn is much larger than Chicago -- twice as many undergraduates, more graduate and professional students. Plus, it is adjacent to two other universities to the north and southwest: Drexel (engineering/business) and University of the Sciences (mainly pharmacology). The student population of the Penn neighborhood is easily three or four times that of Hyde Park. </p>
<p>Penn offers a much more traditional college culture. Frats and sororities are important to social life. People care about sports, especially football and really especially basketball -- games regularly sell out. In general, more partying happens (although Chicago is hardly a party-free zone, and Penn students do plenty of work).</p>
<p>Penn is much more connected to the mainstream of life in Philadelphia than Chicago is in Chicago. It is the largest employer and landowner in the city. The current Mayor and the Governor of Pennsylvania are alumni. The Governor makes it to a lot of basketball games. The University of Chicago is a little aloof from the city of Chicago.</p>
<p>Penn has scads of students from the New York metropolitan area, and in some senses it's very New York-oriented. (Manhattan is only an hour away by train.) That means, if you're not used to it, lots of people can seem aggressive, loud and rich. Ostentatious displays of wealth are not frowned upon. That also means that, in addition to the alumni network in Philadelphia, there is an extensive alumni network in and around New York City. Chicago is more Midwestern, softer-spoken, lower key, less competitive. </p>
<p>Really, the two colleges are more similar than they seem. They just seem very different -- different feels. Lots of people apply to both, lots of people choose between them, but most people know instinctively which one makes them feel more energized and more comfortable.</p>