Next time you go to Chicago, drive out to the north suburbs and take the Ferris Bueller tour. Start off at Glenview High School. This is the school they used when filming, you can pretend to pick-up Sloan, and drive wildly away.
Next, hop on the interstate and cruise into the city. Make sure to stop at the Sears Tower and peer down at the city from the tallest building in the country. Next visit Chicago Board of Trade mock the traders' funny hand gestures a'la Cameron. Before you leave the city stopping at the Chicago Art Institute and be dazzled. I don't know if there will be a parade going on, so you can hop on a float and sing.
As you head back to the suburbs, skip the interstate and take Sheridan Drive (Lakeshore Drive changes names at this point). This will drive you through the ritzy suburb of Ravinia, named for its ravines. Imagine what your car would look like if you kicked it off of one. Probably a lot like when Cameron kicked his dad's car.