It's (Most Likely) My Kind of Town

So Hugh and I are going to Chicago on the 14th which is last minute but fun and I am rather excited because I have never been there and also, I get to wear a coat.

We have friends who are maybe moving/transferring and Hugh has some business to take care of so it just sort of came together... but it is also about twelve kinds of ridiculous because we come home on Sunday, and the very next day the kids and I leave for Hawaii (because my mom just got married and we want to celebrate) which is a lot of travel and makes one feel like a shabby planner.
I am hoping to eat here and meet her, but I would welcome any and all suggestions for important things like - excellent shoe stores and smooth cocktails and, do any of you live there?