I like Chicago...no, I love Chicago...no, I fucking worship
Chicago and would almost sell my soul to get back there!

Chicago is proof that the Midwest is not all backwards, barefoot, pregnant, and like me.
Seriously though, my first trip up there was in 1992 (went to the Museum of Science and Industry and the John Hancock Tower). I also spent a ton of time up there in 1998 and 1999 (as my ex-fiance lived there at the time). Tried to move up there twice (1997 and 1999) without success. It's simply a fascinating city...great museums, great neighborhoods, great culture. Whenever I went up there (which was generally once or twice a month), I would just drive around the entire city (which is huge), go to places that felt a world away from Michigan Ave, destroy the front end of my car (thanks to those lovely potholes), and ride the El to wherever it would take me.
My personal recommendations:
--Don't go up in the
Sears Tower on a cloudy day. Go to the
Hancock Tower...it's not THAT much shorter.
--There are two excellent hotels that are relatively inexpensive and close to the Loop.
The Cass Hotel (on Wabash and Ontario) offers a nice room with cable and a superb location for $59-79 a night (which is super dirt cheap).
The Days Inn Gold Coast is on N. Clark by Lincoln Park and offers an older style hotel complete with rooftop and lake views and a convenience store downstairs (that sells alcohol)...$79-89 a night. (There is also free shuttle service to and from O'Hare.)
--Unless you are die hard, don't even bother driving in Chicago, especially the Loop. Parking sucks and is expensive. The
El and CTA buses will pretty much take you anywhere you want to go, including O'Hare and Midway. Buy a visitors pass. You may even get lucky and find a bellhop that will give you one.
--Stay away from South or West Chicago, unless you are going to Jackson Park (U. of Chicago, Museum of Science and Industry), Comiskey Park, or Hegewisch. Most of the rest of the city is fairly decent.
More information and observation available upon request...