Well I guess I would need to know what type of entertainment you are looking for In Chicago there are many places to visit and on Mondays you can get into the museums for free. Rush Street is for downtown shopping and dining. Depending on if the Chicago Cubs are in town Wrigely Field for American baseball is an adventure. I would for food recommend Gino's Italian steak house with the aged steaks. If not that Chicago has a large Polish population so there is that. Really, in Chicago you can go from area to area to sample almost all the world's cusine. I plan on going there with my wife in October. Of course then it's American Football season