Depends on what you're into. Chicago is such a huge city, there's something for everyone. Just stick to the city and don't get stuck in the burbs. The theater is huge here, Second City is here, tons of great restaurants, concerts every night of the week, shopping, museums (the Art Institute, Museum of Science and Industry, Field Museum, Museum of Contemporary Art), Chicago Bulls, Chicago Blackhawks, etc, etc, etc, etc.
I'm not sure where you're coming from, but don't be afraid to use public transportation to get out of downtown and explore some neighborhoods. Also, don't miss an opportunity to walk along the Chicago River downtown at night...it's stunningly beautiful.
Thanks Dollface, I'm open to anything. Most of my free time is during the week in the evenings. I'll have to check out the river and a few restaurants. If there are any mature ladies looking to show a guy around please feel free to mail me.


