My $0.02 (if it's worth even that-- I'm not applying this cycle): Go to Madison. I think Chicago is a 1-1.5 hr drive away, it is a very natural market for grads and summer associates. And while you may now be certain of your desire to work in Chicago post-graduation, you never know what your future will bring. Suppose in 20 years your spouse needs to move to DC for work? Or Cali? My guess is that your Wiscsonisn degree would be significantly more portable than a degree from one of the Chicago schools. I know that it shouldn't really make a difference where your degree is from after you've been out so long, but I think that in many cases it does.