I lived in
Wicker Park back in 2000-2001 and in nearby
Humboldt Park. I agree 100% with the assertion that you will see every imaginable type of person on the street there, it certainly adds to the uniqueness of that area.
What makes that fact so interesting is that Chicago is a town of diverse neighborhoods where you usually will only see people that "belong" in a given neighborhood. It's also what I find most disturbing about Wicker Park. Here you have vanity in it's most disgusting form of just moved there from Schaumburg yuppies with their german cars and overpriced condos living right next to people who don't know how they are going to afford their next meal.
I left because it was so sad. I miss it because it IS close to the Loop, has a nice central location and some great nightlife. I don't miss all of the snoot, ignorance and dispair.
Here is a nieghborhood that serves as a prime example of Chicago gentrification. The place was a Puerto Rican ghetto for the last twenty years or so and BTW--people who lived there in those days called it Humboldt Park, Wicker Park is something created by the real estate development companies to lure yuppies so as not to scare them off with the stigma that Humboldt Park bares. Then comes the poor artsy white people, then the hipsters, then the yuppies, and the future looks real bright for Mayor Daley.
Most of the artsy types moved on the the Ukrainian Village neighborhood or Humboldt Park some time ago and the hipsters are starting to follow. If you have money to invest in real estate, do it here, you will cash in nicely in a few years or so. It's too late to do that in Wicker Park really, the rents are high and all of the good property is taken by those like you.