Ferris Bueller Tour
All you need to do is watch the movie and do your best to recreate as many of the scenes in the movie as possible. Go to the top of the Sears Tower, go to a Cubs game, if there happens to be a parade you can check it out and maybe lead a huge dance (okay, so maybe I'm the only one cool enough to pull it off). But I try to do even some of the little things, like take a cab with some friends and con my way into a really nice restaurant with no reservation.
Chicago is one of the best cities in the world, and so few films have every really portrayed it as such, but Ferris Bueller's Day off was definitely one for the ages, and I think it's a great way to have some fun. I'm planning on trying it again soon when some of my cousins come for a visit!