The Art Institute of Chicago is any art history fiends daydream. This huge museum has tons to look at and will not disappoint. Walk over to the Buckingham Fountain afterwards for a picnic lunch.
John Hancock center/observatory –You can pay money to go to the top or you can just get brunch or lunch at the restaurant on the 54th floor. I suggest the restaurant move. If you go during lunch you can actually feed two people for about 25.00, which is about the same price the observation deck would have cost you.
Sears tower—They guard this place like it houses the President. You can only go in during certain hours, you can only go to the observation deck or shops, etc. So make sure you enter the correct door and come during business hours.
Wrigley field—Catch a game here for a reasonable cost. The stadium is open, large, and is always packed. Like everywhere else in the city, you can take the train here.
Navy pier—This place is hopping at night. You can take the bus to the pier, make sure you head home before the last bus leaves without you. Restaurants, shops and usual city park entertainment. On holidays you can see fireworks!
Millennium park –This is the city’s cultural center where you can walk through free art galleries or rent bikes or segways.
Field museum—This place is known for the the largest/most complete T-rex
If you prefer smaller towns with lots of history, then
Another smaller town with something fun to offer is
Tinker Swiss cottage is a Victorian mansion with a Native American burial
Last but not least is Metropolis. What town names Metropolis could not be dedicated to Superman? They do not disappoint and are the home of a Superman Statue as well as a Super museum.