Chicago has excellent restaurants and the architecture is stunning. Take an architectural cruise if you have the time. In the main areas for tourists, there are many options for entertainment. As always in major cities, be aware of your surroundings but Chicago can be fun especially in the summertime.
I did the architectural cruise and it is a must do! As CS says, the buildings are stunning and we didn’t have a bad meal there. Highly recommend a Chicago visit. I thought it would be a cesspool but then learned where the bad neighborhoods are and they are nowhere near downtown.