While he is in business meetings during the day, there are a bunch of things you can do! Like everyone said, shopping, museums, etc. The Architecture Foundation does walking tours around the city, Chicago has some very interesting architecture, so I would definitely recommend those if you like that kind of stuff. http://www.architecture.org/ The Historical Society also offers tours, but I believe most of them are on the weekends... so hopefully your SO won't have meetings then The Wendella river boat tours are another great option. Personally, I don't get the appeal of Navy Pier, and probably never will... maybe if I had little kids, I guess. However, there is a great Shakespeare Theater there, and there are evening cruises that take you out onto the lake for great views of the skyline at night. Also, on a Saturday night you would get to see the sky line and the fireworks which are every Saturday - or Wednesday (I think) - night from Navy Pier. If the weather is nice enough, check before you head over here, you can always relax and get some sun on the beach too! I don't want to repeat what others have said, you have gotten some good suggestions Oh, and another place for you to check for things going on before you arrive in Chicago is Metromix.com lots of listings of events, restaurants, etc.