Strangers with Candy: The Movie
Strangers with Candy shares many of the same qualities as Napoleon Dynamite, but a quality which made Lisa and I hate the latter, and reaaaally hate the ensuing Napoleon Dynamite pop cultural CRAZE, is thankfully lacking in Strangers with Candy
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For other touristy stuff, the Field Museum has quite a nice permanent collection and usually gets the best rotating exhibits, too. Been a while since I visited the Museum of Science and Industry (located on the campus of my alma mater, the University of Chicago), but it can also be fun. It's just that it has more exhibits geared towards the education of children. And DEFINITELY make your way to the Art Institute. GREAT collection there. Chicago museums have free days during the week, too, so find out which one is when, and hit 'em up.
Chicago's theatre and improv scene is very impressive. Check out the famous Improv Olympic (also has one night of free comedy, maybe Tuesdays? or Thursdays?) and Second City, natch, where Amy Sedaris first cut her teeth. You also won't have to look very hard to find good plays for a good price downtown in the Theatre District.
You're into music, as well, and Chicago has a great indie scene. I'd look at the Chicago Reader's website before you go and figure out who's playing where.
As far as neighborhoods, I can recommend Boystown (Belmont and Halsted) for the hot gay guys and good shopping, Andersonville for the friendly dykes and ambiance, Hyde Park for the gorgeous old mansions, and Wicker Park for the good music stores and an opportunity to trip hipsters.
For a nice night's excursion, go to the Brew & View at the Vic, off Belmont and Sheffield, in Boystown. For a small fee, you can sit and watch a recently out of rotation but not yet on DVD (imagine hypens between those words) big screen film while sitting at a table, and order a cheap pitcher of beer as well. That's always a good time.
Hope any or all of this is helpful! I'm envious, I can't visit Chicago for another five months or so.
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