Vanderbilt by a mile.
People have called me a Vanderbilt hater on this forum because I say the truth: Vanderbilt is not a great school for non-white students. I still believe Vanderbilt is not great if you’re a minority as the prevailing culture is white and faux-Southern. Northerners, Mid-westerners, and West Coast kids pretending to be from Mississippi.
That said, I would go to Vanderbilt 100 times before I would go to UChicago. Much of Chicago’s prestige is due to it’s graduate programs. So if you’re CURRENTLY applying for a PhD in Econ or an MBA, I would choose Chicago over Vanderbilt. But for undergrad, the experience you’ll receive at Vanderbilt is much better than the experience you’ll get at Chicago.
UChicago does the same stupid grade deflation that Vanderbilt does. So you’re going to be similarly hurt grade-wise by going to Chicago. Also, Chicago students are not fun. The campus is boring. The Nobel Laureates are grad students.
Summary: If you love greek life, having fun, great academics, and prestige bs, then Vanderbilt is absolutely for you. You can go to Chicago for some economics/finance related grad school and get more prestige than you would as a Chicago undergrad. Same goes for Johns Hopkins, Cornell, UPenn, Brown, and Dartmouth.