<p>Apply EA to Chicago then regular decision for Penn, and make your choice in April if you get into both. That being said, Penn has a significantly greater party atmosphere than Chicago. You can find parties at Chicago, but you really don’t have to go to them to have a social life. As an aside, as a student at UChicago my experience has been that the people there are really smart, interesting individuals who care about learning.
Oh, and JHS brought up a big point with fashion at Penn. It’s almost not a thing at Chicago, which I find to be really relaxing. My understanding is that Penn has a much stronger prep school vibe…</p>