If you aren't from the area, Portillo's is a MUST to try for food. They are located all over the Chicago-land area and serve up the best hot dogs, beef sandwiches, and more!
Chicago Craft Beer. It's all great, but we personally recommend Anti-Hero or Hazy Hero.
A fun place to have a unique beer and with reasonably priced food in Chicago.
A fun, not so regular cinema to stop in to take up a few hours or so. Also with a location in Chicago proper.
If shows are running, a great place to see a comedy show
On the 95th floor of the Hancock building, you can make a reservation and enjoy a drink while looking out over the entire city.