A good source of info on "what's happening" in Chicago for young or young-at-heart culturistas is:

http://www.chicagoreader.com/

(The Reader was the "underground" paper of my teen years in Chicago....now it's a standard source of info -- similar to a "Time Out".)

Chicago has a "Lonely Planet" guidebook, so it's a fully acceptable place to visit.
(New edition of book due April 2011, see updates at
http://www.lonelyplanet.com/usa/chicago/sights)

FYI: As with most American cities, the NORTH of downtown/center city is the more affluent and caucasian area.

When I need to impress NooYawkers:
The Art Institute has more of the crucial "Haystack" and "Water Lily" impressionist paintings on regular display than any other museum.
In the John Hancock skyscraper, it's the top 50 or so floors which are apartments (rather than offices). So the people who actually live 80-90 floors up do live the highest above local ground level of anyone in the world.
Beaches downtown and nearby!
The Bahai temple for North America is north of Chicago.....the Bahai have just one temple on each continent (if you're collecting), but it's not in NYC or LA!

Oh....if you're looking for a hotel in a fun neighborhood area, consider the Hotel Indigo Gold Coast (part of the IHG-Holiday Inn system) at 1244 N. Dearborn Pkwy, Chicago, IL 60610.

Enjoy!