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Both schools are wonderful so your S can't lose. A few differences that we noted:
1) Oberlin is, of course, a bigger school-almost double the size- so more choices for classes and more options extracurricularly.
2) The music conservatory ensures that there is a very, very active - and high quality - music scene. We were told there was a differernt performance every night of the school year. But your S will be primarily a viewer unless he is an extremely talented musician. (Our S loves music and likes to perform-but realized he wouln't get much chance with so many potential professionals at the school.)
3) Cleveland has more going on than Des Moines or Iowa City-and its marginally closer (by about 15 minutes, I think). If having a somewhat more urban area nearby matters to him, that's something to consider.
4) Weather is marginally better in Ohio than Iowa in the depths of winter and transport in and out of Cleveland can be easier-more flights than Des Moines.
5) Oberlin has better name recognition among the general public (although not among grad schools, where both are highly regarded).
So why did my S end up at Grinnell?
1) The academics, especially in the sciences, seem to be a little more demanding and intensive. Since he's a science guy, we looked hard at the caliber of the faculty, facilities, coursework, research opportunities and outplacement for kids in sciences. (We didn't spend as much time looking at the humanities, although were we especially impressed by the support for developing solid writing skills.)
2) Smaller introductory classes (none bigger than 30 and most max out at 24). See (1) above-lots of writing, class participation, etc... This also means that professors get to know you extremely well in terms of providing mentoring.
3) The facilities are new and gorgeous! There's a fabulous new student center (Oberlin didn't have a central student center that serves as a campus hub - at least when we visited), science building, etc... (Of course, Oberlin has a new science center too, which is very nice.)
4) Very personalized advising and no core requirements. The advising is one place where Grinnell excels.
5) The smaller campus and greater isolation has a positive: The student body is extremely inwardly focused - it's you and your friends who are creating the fun. There are no by-standers at Grinnell. If you are not participating, you are watching your friends participating.
6) The very large endowment at Grinnell means that they have money for almost any ideas that students come up with for clubs or activities, and they also are very easy in providing money for internships.
Also, culturally, the two are a bit different and not just because of the music scene. The predominant culture at Oberlin is strongly oriented towards social justice and activism. Grinnell leans more quirky and individualistic. But this is more nuance than substance. That midwestern understatement is present in both cultures.
As you can tell, we really like Oberlin and he had a hard time choosing one over the other. Ultimately, when you are talking about two schools that have more in common than they do differentiating them, it really comes down to the kid's interests and their personal 'fit.'
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