If I lived in Chicago, I would...
Simply HAVE to visit the Sears Tower on a day that it is not cloudy. Last time I was there was 1985 and we could not even see the top of the tower due to clouds. We decided not to go up.
We flew in and landed at O'Hare and then made our way to Grand Central Station. Or was it Union Station? I would go and visit it again. In fact, I would gladly "TRAIN"-in to the station.
If it was the right time of the year, I would drag my companions to the Old Town School of Folk Music to the Square Roots Festival and Craft Beer sampling event. The school has a lot going on and a lot of different activities.I think I would be remiss if I did not go to Hull House. That would, of course, necessitate rereading the Jane Addams biographies. Maybe I would choose a more scholarly one than the last I read in 1966.