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I've heard that UChicago tends to favor transfers from the surrounding area... does that extend to UIUC? Or only like Loyola and Kent, etc.? I just figure since UIUC is a few hours away and better ranked, it might enjoy some of that favoritism lol. Thoughts?

There were 3 transfers from Kent, Loyola, and UIUC, if I recall correctly, each of which were more heavily represented than other schools for the most part. I think Illinois may be preferred, although this may depend on you personally being from the area. I say this because a friend of mine at Illinois were pretty comparable (he was a grade increment up on me, though I had an extra CALI award) and I got accepted as a transfer at Chicago and he did not. We think my having lived in Illinois have for just about all of my life (and his having not) may have been a deciding factor.

In any event, the transfer class size (23, in our case) is so small that it may very well be a crapshoot whether or not you are admitted.