Sorry I am late with the reply, had to go to work for a few days. We had a great time in Chicago, went to the sears tower (awesome at sunset but there is a stupid movie you have to watch so budget some time if you are trying to hit sunset) and some good pizza. We tried a couple and liked Lou Malnati's best. The concierge suggested the lounge at the John Hancock building instead of the Sears tower (make sure you go to the lounge and then the lift is free os something like that), he felt the view was better. Maybe nextime for me on that one as we only had a bit of time. We went to the Sears tower because I felt obliged as an ironworker to go to the crown jewel for our trade.
If you care, there is a Bath and Body Works in the train station. It seems women everywhere love that crap so it might be good for gifts or something. Maybe you like it, I'm not going to judge, but I don't like it. Nope, not me.
I hope you don't have to park down town, it is like $30+ per day but there are lots everywhere.
The fountain is under repair, The Art Institute is under construction and you can spend all the money you want on the miracle mile so have fun.