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With just a little bit more $$ offered from mich, is there any compelling enough reason to pick mich over uchi for Chicago biglaw. I think i would enjoy the culture and the college campus/ambiance there more, but probably need to grow up and think more long term. Is there a decent success rate negotiating more money out of mich?

It's going to be pretty damn tough to beat UChicago for Chicago BigLaw. If the difference in money is small, there's not a great reason to pick Michigan. I think I would enjoy my time at UM more as well, but your career goal keeps that from being much of a consideration, IMO.