C.L.
Someone posted this question a week or so ago if you want to check the archives. I second most of the posters, but also would recommend the Children's Museum on Navy Pier. My son loved it when he was about 8. It's also fun just to run around and see the fountain in Grant Park and see the sculptures in Millenium Park. I don't know if anyone has recommended Lincoln Park Zoo, but it always used to be free admission. It's the perfect zoo for little kids. Do you belong to any zoos or museums in your hometown? Some of the attractions might have reciprocity. When we were there 5 years ago with our kids we stayed at a very family-friendly Embassy Suites right off of Navy Pier. It wasn't cheap, but we saved money on food because breakfast was included and they had a complimentary happy hour with a buffet every afternoon/evening. The rooms also allowed us to have some food and meals in the room. We were able to walk or take public transportation to most attractions. There is also a Hampton Inn downtown very near the American Girl doll store that is pretty family friendly and includes breakfast. Have fun!