I recommend you take one of the canal boat cruises that run along the Chicago river and then out into the lake. It's a great way to see the city and the architecture. Some other must sees include the Shed Aquarium and the Field Museum. If you have time there are a number of excellent comedy clubs and night spots as well. almost 10 years agoAnswered by Stephen A. Joyce via Travellr.com
I agree with taking a Chicago River Architecture Tour. I went on one with Wendella and really liked it! http://www.wendellaboats.com/experience/riverarchitecturetour.aspx
Another great way to learn about Al Capone/prohibition/mobster era is to go on an Untouchables tour (http://www.gangstertour.com/). It allows you to get outside of the downtown area and see many more neighborhoods while hearing tons of really interesting and amazing stories! I'm pretty sure it goes to Green Mill Jazz Club,which has loads of history and is still a popular jazz club today.
The museums are really great, but if you are only here for a few days and want to see more than downtown, I'd suggest looking into some neighborhood tours, which will give you a different experience while learning a lot. http://www.explorechicago.org/city/en/things_see_do/event_landing/events/tourism/chicago_neighborhood.html
I almost forgot about the Chicago Greeter. "Chicago Greeter is a free service of the Chicago Office of Tourism that matches visitors with a friendly, enthusiastic, and city-savvy local for an informal, two- to four-hour insider's orientation to the city"s: http://www.explorechicago.org/city/en/things_see_do/tours/tourism/chicago_greeter_tours.html
Let me know if you have any other questions. There is a lot to do here, but I gave you a few things that can help you have a great time here! almost 10 years ago