Hi Donnie!
First of all, January is probably not the best time to visit Chicago, if you can help it... it's very cold, very windy, and did I mention cold? Brrrrrrr.
Also, do you have tix to Oprah already. I FINALLY was able to get tix last month at the last minute... they're sooo hard to get!
GL!
So, if you do come, there's sooooooo much to see: Sears Tower (of course), Hancock building, Art Institute and museums, Water Tower Place, the lakefront, etc, etc, etc. It's not as exciting (I don't think) as NY as Chi-town DOES sleep!
But, it really is a great, great city!
Are you looking for specifics to do/see? Places to eat? It's all down there. I know when I went to NYC I checked out and got a lot of info off the web at engines like google.com and citysearch.com.
Did that help at ALL? Lemme know.