Re: Chicago Anyone?
We went to Chicago last year. My concierge booked tickets to Wrigley Field the day before without any difficulty. We stayed at the Palmer House Hilton which I thought was terrific.
How about going up some big buildings ie the John Hancock and the Sears Tower? (I thought the John Hancock was the better of the two).
I'm sure you'll have a great time whatever you decide. Chicago is one of my favourite US cities.