Chicago is at the top of my list. I can cosign what you’re saying about their advertising and their mail. One of the first pieces of mail I ever got from any school was UChicago asking what oddball intramural sport I would invent and what I would name my team. While it seems from CC posters that that image of Chicago is becoming a thing of the past, I don’t believe that it can be wholly fabricated, just like you.
Cosign the Northwestern suggestion, but it is in the Big 10, so sports have more focus there.
Since we seem to be attracted to similar aspects of UChicago, I guess I’ll throw out some schools I’m applying to. While Chicago is arguably the quirkiest, most bear similar characteristics and fit in a similar theme. No guarantess you’ll like them, but you might:
Northwestern, Kalamazoo, Vassar, WUStL, Brandeis, Macalester
About finding a few close friends you can connect with (also one of my hopes), I think that student organizations might be something good to look into. While bigger schools have more of these, you might just get swamped. I looked for schools with organizations that I would be interested in but were still small (10k> undergrads)