When tourist attractions include Classics Cafe and the Reg

I have a guest this weekend, a friend from high school. She attends a liberal arts college in the Northeast, and I'm looking for ways to show her how things are done out at a big party school--sorry, research university--out in the Midwest.

So far, plans include showing her Classics Cafe (caffeinated intellectual/ pseudointellectual psuedodating rituals, general posteuring), Jimmy's (drunken geekiness; the oddity, for a New Yorker, of an urban American bar that still allows smoking), the North Side (how a city too cold for tank tops can nevertheless have a thriving gay neigborhood), Michigan Avenue (it's "magnificent"), the Art Institute for the art and the Smart Museum for its cafe's muffins, and, if she's up for it, the big gray thing on 57th Street, where she can watch hundreds if not thousands of U of C students do homework, pretend to do homework, and nap.