Well, I am primarily interested in academics and according to my extremely biased sources Chicago is quite good at placing academics. There is also an issue of my ideological bent - I am theologically, politically, and jurisprudentially conservative in a way that makes Chicago a better fit. That's a lot to unpack, but it is certainly a consideration for me.
But primarily there is the issue that I don't really have my hopes up about getting in to HYS in the first place.
I don't want to hijack this thread, but, to be fair, this is part of my broader decision-making as to whether to apply ED to Chicago.
Chicago's academic placement is better than most schools (though certainly not better than Harvard and Yale, so... yeah....) but you need to keep in mind that academia is a long-shot for anyone, and particularly for a transfer student; especially given the very long odds of making Law Review. (I've looked into it.)
Also: While there is certainly a stronger "conservative contingent" at Chicago than elsewhere, it's not like it permeates the school, and it's not like you couldn't find like-minded folks elsewhere. Regardless, Evidence is Evidence, Securities is Securities. The only time it's really going to come out is in seminars--and then, only certain seminars.
And I have no idea what you're talking about when you call a school "jurisprudentially conservative": Yes, Easterbrook and Posner teach one seminar a year and participate in some workshops. But so does Wood. Also, "theologically" conservative? What? It's not Notre Dame.
ETA: None of this is to say that Chicago isn't an amazing school. It is. My comments were only addressed at people who have a reasonable shot at HYS, and whether ED makes sense for those people. I've had a few years to dwell on the what-ifs, so I share my view; at the end of the day, I met my wife-to-be at Chicago and my career is going to go just fine. That doesn't mean that I still don't question where I'd be had I waited and gotten in to HYS--even beyond the fact that my loan balance would probably be $50k+ less than it is now.