JHS,
For your reference, I purposely left out Phila-area prep schools (schools that I believe you’re referring to) because they skew so strongly towards one undergrad, Penn. To give you an example, here are college matriculation numbers at Germantown Friends School, arguably the top private school in the Phila area:
http://www.germantownfriends.org/admissions/college-matriculation/index.aspx
Technically, Brown U is the third most popular choice amongst GFS grads, with 15 grads going on to Brown in the past 5 years. That number doesn’t hold a candle to the top recipient of GFS grads, Penn - which had 57 GFS grads matriculate in the past 5 years.
Those numbers are similar at lots of other Phila-area private schools (Haverford School, Episcopal Academy, etc.), so I didn’t even bother putting those schools on the list. Frankly, they are feeders to Penn first and foremost, with the rest of the top students scattering to a wide range of schools. In this way, they differ from the NYC prep schools and certainly the prominent boarding schools, where no one undergrad is so disproportionately represented. I’m not sure why the Phila schools are this way, but that’s how it is.
Re your broader point, yes, Chicago was certainly popular back in the day amongst a subset of prep school students. It never, though had the broad popularity and allure of schools like Georgetown, Brown, Yale, etc. Those were the schools that large swaths of the class wanted to go to, and the numbers backed that up. It’s why if you look back at old Andover/Exeter data, Chicago is popular (with 4-6 students every year going there), but behind Yale or Brown (8-12 every year, at least).
Now, Chicago - at many places - seems to have bumped up in terms of receiving broader interest. I don’t think, in the past 5 years, the subset of academically-minded students at Andover or Exeter has increased that much. Rather, Chicago seems to be targeting a broader subset of the A/E population, and succeeding in recruiting these students.
It goes toward my thesis that Chicago is succeeding in attracting a broader swath of these prep students. That has to make some sort of impact on the student body, which, in my day, was about as academic as you could get.
(Also, zinhead, Chicago is also making strides in attracting URMs and first gen students - it’s actually a market leader in terms of scholarships/programs offered for these students. I think the end result then, is that the classically quirky [probably white] Chicago student is not as well represented now as he/she was in the past.)
HydeSnark, a final comment - you said that the dorm can tell more about the student than anything else. In my day, ALL the dorms were known for being fairly quirky. Snell-Hitchcock may have been a bit more quirky than others, but Burton-Judson, the Shoreland, Breck, Woodward, etc. ALL had iconoclastic vibes. Now, it seems that not all dorms are like that, and that in and of itself is telling.