Our hotel was inside the loop, so we were pretty centrally located, both for my work engagement and most of our sight-seeing activities. Although all the locals were acting like it was really cold, it was not bad at all, which is a nice break because we did not rent a car; instead, we bought 3-day transit passes and relied on the trains and buses to get around, which forced us to be intrepid but actually went just fine.
I was most impressed with the size and scale of Chicago - it makes Minneapolis look... quaint. The buildings are much bigger and there are many, many more skyscrapers than anywhere I have been except NYC. We mostly grooved on the architecture this trip, taking a guided tour put on by the Chicago Architecture Foundation that shot about half of the day on Friday, although we saved time for riding the L to scope out some more buildings and to eat pizza at what is supposedly The Place for authentic deep-dish goodness as well. Saturday we hit the Art Institute and Shedd Aquarium and walked the City some more. One of the best views of the skyline was from the museum campus, it turns out.
All in all the trip was ridiculously easy, so I expect we'll make it back some time relatively soon. It would be nice to hit it in better weather since they apparently have an extensive trail system along the lake that would be nice to ride. More photos from the trip on the Flickr site.