Yes.....get yourself some roast beef from a corner deli.....there is one about every 2 blocks on the north side.
Buy you a case of Old Style Beer......best cheap beer on the planet.
Speaking of Planets......hit up the adler planetarium. I haven't been there since I was 10, but I thought it was cool. And the Shedd Aquarium. Sears Tower is overrated.....maybe because i dont like heights. Its kinda cool lookin out over the city.....but make sure its a clear day.....other wise you probablly wont see shit. The museum of science and industry and the field museum of natural history is tight. At least they were when i was 10.
Basiclly everything of interest is right off the lake downtown. Take in a Bears game if you have time. They are only the best team in the NFL.
As for shopping.....Nike Town is a must. Yorktown and Woodfield are the the best malls....in 1992. But they all out west.
Portillo's has the best hotdogs in the world. Heat Myser will probablly dissagree, but that place is like a Chipotle for hot dogs. And they have some dope glasses for beer that are worth stealing.
Salerno's has the best pizza......I lived out west and we always went to the one out by Forest Park.
And if you're up that way, hit up wrigleyville. Lots of cool places to eat and hang out if you're into that shit.
But yeah if all else fails, go catch that Jordan guy at Chicago Stadium. Or the second best thing...a Chicago Sting game.