<p>(I'm a parent with relatives and friends and their children who have gone to both schools, including a daughter currently at Chicago.)</p>
<p>There are really huuuuge differences in the feel of the two schools, so it really depends on which qualities you value most, and whom you want to hang out with:</p>
<p>Wesleyan is very isolated. It's hard to get anywhere (other than Wesleyan) you might want to go without a car or a friend with a car. The best restaurant in Middletown is just awful. But that means the students at Wesleyan work much harder at entertaining themselves and each other than those at Chicago. Chicago is actually more isolated than it looks, since it is something of a haul to get from Hyde Park to popular places in the city, but $2 and 60 minutes will get you pretty much anywhere you want to go in a world-class city. Compared to Wesleyan, on-campus life is stunted. If you want your dorm to be a fun place, Chicago is not a safe choice. It's not completely true that Chicago is "where fun goes to die," but no one ever even thought to say that about Wesleyan.</p>
<p>Wesleyan = THE bastion of left PC thought. People take it seriously, and do it for the right reasons. Wesleyan sometimes seems to parody itself -- the last time I was there, it was Gay Arab-American Awareness Week, there were extensive, heartfelt debates about administration attempts to stop students from chalking graffiti on all the sidewalks, and there was also discussion about shifting a women's club team to a co-ed league because the existing league would bar (hypothetical) transgendered team members. I'm sure there are conservative students at Wesleyan, but I'm sure they feel very like an embattled minority. I'm not sure there are lots of conservative faculty there. Chicago = a broad spectrum. Like most universities, the faculty is generally left-of-center; unlike most elite universities, the most famous faculty are on the right (and, historically, on the far right). So the school attracts ambitious, articulate conservative students to a far greater extent than Wesleyan. </p>
<p>So, for example, at Wesleyan I would expect to find a lot of debate about the ethics and politics of resistance to the Iraq war, and analysis of the effect of imperialism and racism on U.S. policy there. At Chicago, you could still get a serious debate on whether the war was justified (to a large extent, the war is arguably Chicago's fault, since many of its most ardent supporters passed through the university and were followers of famous Chicago political philosopher Leo Strauss).</p>
<p>Chicago tends to attract socially awkward kids, too. So it's not always easy to get the party started. On the other hand, the percentage of substance-free kids at Chicago has to be many, many times that of Wesleyan. I think the culture at Wesleyan is such that if you're not in a sub-free setting, you have to be comfortable with being around a fair amount of substances and people using them. I don't think Chicago has substance-free dorms, but there are many dorms, or floors of them, where the weight of peer-pressure (with official backup) forces all but the most discreet substance use (or, for that matter, noise) somewhere else. Also, at Chicago the majority of kids live off-campus, usually their last two years, but often the last three -- convenient off-campus housing is plentiful and cheap -- so you wind up controlling your space more than at a dorm-centric school like Wesleyan.</p>
<p>Chicago just isn't a party-hearty place (although there are always pockets). Wesleyan (adjusting expectations for its high academic standards, etc.) is.</p>
<p>Chicago, I believe, has a much higher proportion of students interested in the sciences than Wesleyan does. At the grad level, Chicago is world-class in some scientific areas, especially physics; Wesleyan isn't. Of course, that means more personalized attention from faculty at Wesleyan, less cutthroat competition, and less peer stimulation.</p>