Go up in the John Hancock building, its not as high as the Sears tower, but it also has an amazing view. Go to Navy pier and ride the big farris wheel, it has a great view as well... sort of smelly down there though being near the water... take a walking tour, go to the Field Museum, Go see the Giant silver bean in Millenium Park, go to Oprah s studio...hope that helped :)
Visit the museums, the lakefront, Navy Pier, Millenium Park
I miss Chicago. :( I grew up there, now we live 2,000 miles away. You could go to Lake Michigan.
Whore yourself.