Quoted By:
Can she handle the cold? Honestly, a second date out in this weather would suck ass.
I can, however, recommend ice skating and museums in Chicago. Go downtown during the day hitting up the Field and the Shedd and spend the night in the Rosemont area iceskating (there's also some decent places for dinner/bar right by the outdoor skating area). Since you're between Milwaukee and Chicago, I presume you'll take 294 home... you'll be able to see the Rosemont area with the bars/skating right off 294. (If not, there's a long wait to ice skate millennium park)
Or have yall can come down and hang out with me at my favorite bar "kind of downtown" drinking craft beers, but I live far out of the city and only spend time in the area whenever they have a good selection on tap and I'm not stuck working a shift at the hospital.