Start at the Sears Tower Skydeck. Next head over to the Art Institute. End the day with a Boat Tour on Chicago's River.
Start out with some Oak Steet Shopping. See the Cubs, Canoe, or Ice Skate at Millenium Park.
Visit the Field Museum of History, Adler Planetarium, and/or Shedd Aquarium, they're all in the same location. Or one of the many other museums.
Take the El to a neighborhood for a day of culture, site seeing, lunch and shopping. Watch the Neo Futurists perform 30 plays in 60 minutes.
Try the deep-dish Pizza, a thick Chicago steak, or a hot dog -- remember celery salt and no ketchup.
Shop Michigan Avenue, then hop on a Trolley and head to Navy Pier for a spin on the Ferris Wheel.