I would recommend going to the school at which you think you would be happiest -- I say that for any school.
I was getting ready to turn down my state school in order to reapply to MCW the year after I initially applied because I knew I wouldn't be happy at my state school. I didn't want to be miserable for 4 years of med school after being miserable for 3/5 years of undergrad.
The stuff you learn at each school will basically be the same, so that shouldn't make a difference, but the way in which it's presented, the city, the student body, etc, could.
I would advise against looking at the Milwaukee weather right now though.