There are a number of different tour companies that all do a great job, but we'd recommend the tour done by the Chicago architectural center
The Art Institute of Chicago
111 South Michigan Avenue, Chicago, IL 60603
Spend the day browsing the near endless gallery, home to some of the most famous American works, including Night Hawks and American Gothic, and iconic classics like Monet's Water Lilies, and Van Gogh's The Bedroom.
Chicago Pizza Tours
27 North Wacker Drive, Chicago, IL 60606
Experience one of Chicago's most iconic foods on this tour, where you'll get to try multiple pizzerias and learn about the history of the deep dish.