The art institute is a must. Wife and I went 12 times a year when we lived there. We typically spent 4-5 hours each time. Take your time it is amazing to see all those works of art. You can also find many galleries on side streets of Michigan Avenue - most were free to enter when I lived there years ago.

Go up to the signature lounge, 96th floor of Hancock Building, for a martini.

Definitely agree with previous post about food. Determine what ethnic food you love or would like to try and go from there. Since I've been away from Chicago for years now, the only site that comes to mind to get a headstart would be metromix.com.

Go to a cubs game, bleacher seat, if you can. Not interested in baseball - anytime before, during, and after a game in wrigleyville in 'most' bars is an interesting time.

I got a kick at just walking around the city. You feel like an ant in awe. I'd recommend the Mile, Gold Coast, Lincoln Park, and the lakefront. The lakefront is a prime area for jogging/walking, biking, and rollerblading.

If you want a laugh, try second city. They have great shows.

I'd stay on the mile or close to it. Peninsula, Drake, and the W are all good. Ride the l at least once.

Other things that are OK - navy pier to people watch, other musuems like shedd etc., tavern on rush friday early evening, and boat tours.