Gosh that sounds like so much fun. I wish I could show you around, but I'm way too busy with work and I'm flat broke at the moment.
For some suggestions to visit: There's boy's town near Wrigley Field, I have several gay friends who hang out around there and have mentioned that a good deal of T-girls go there too. Millennium park with the bean is a classic, Going onto the sky-deck of either the sears (Willis) Tower or John Hancock Building are fun, Navy Pier is a cool place to visit, the Museum of Science and Industry is pretty neat too. The shedd aquarium is cool along with the field museum with the T-Rex Sue. These are some of the coolest places to visit while in Chicago. Also don't forget to go shopping down the magnificent mile

(Michigan Ave).
Hope these places provide you with a lot of insight to our beautiful city (albeit all the corruption). Hope you find someone and have lots of fun

Love,
Marty (Sammi)