The best way to go sightseeing in Chicago and to know the city a bit is to take a walking tour. This is also perfect if you don't intent to spend a lot of money while in Chicago. There are many travel guides who can take you on a walking tour of Chicago you just have to contact the right person or company suitable for your individual needs.
1. Examples of Chicago walking tours
http://www.chicagotraveler.com/tour-chicago-by-walking.htm
- Chicago Chocolate Tours
- Chicago Gold Coast Walking Tours
- Chicago club Wrigley Field Tours
- Chicago Historic Pullman District Walking Tour
- Chicago lakefront Walking Tour
- Chicago Food Planet- Food Tours, and
- Chicago Red Cap Walking Tours
http://www.allgetaways.com/region.asp?areaid=100944
2. Other Tips
Not all the walking tours in Chicago are offered all year round hence consider checking online if the kind of tour you are interested in will be available at your time of travel or not. If you can, you can adjust your travel arrangements to coincide with the walking tour you want.
http://travel.nationalgeographic.com/places/places-of-a-lifetime/chicago-walking-tour-1.html
If you have a disability, consider getting a travel guide Chicago IL who has the necessary skills and tools to give you a fulfilling walking tour.
http://www.walkchicagotours.com/