Of course you’ll want to sample the famous deep dish Chigago-style pizza. Here’s a list of some favorite places on Yelp
Go up to the skydeck at the Willis Tower (formerly known as the Sears Tower). It’s the tallest building in the Western hemisphere.
If you’re interested in history, you might enjoy visiting the oldest house in Chicago, The Henry Clarke House Museum
The Field Museum of Natural History, is supposed to be one of the best in the country.
You might enjoy a view of Chicago from the water with a Boat Tour or a Water Taxi
Here’s a list of Delis in Chicago to find the 6 Best Italian Submarine Sandwiches
If you like Guy Fieri’s Diner’s Drive-ins and Dives here’s a list of some of the Places He Ate in Chicago.
This sounds like fun, a Murder Mystery Dinner Theater
If you have an interest in one of the most famous modern architects of all time, you might enjoy a Frank Lloyd Wright Tour
If you like movies, you might enjoy a Chicago Film Tour that showcases sites around town where various movies were filmed like The Dark Knight and Ferris Bueller.
In addition to the Art Institute of Chicago, there is tons of outdoor Public Art all over Chicago.
If you are interested in architecture, art, or Christianity, or history, you might enjoy visiting some of the beautiful churches in Chicago, like St. Michael’s or St. Mary of the Angels or Old St. Patrick’s
I hope you have a marvelous trip!