Resources on the Web:
From the Chicago Commission on Landmarks:
Historic Woodlawn and University Avenue, Hyde Park, Illinois
Your House Has A History: A superb booklet published by Commission on Chicago Landmarks with step-by-step instructions on house history research and a guide to obtaining resources such as building permits, indexes and tract books, and construction reports. (It is a large .pdf file, requiring Adobe Reader.)
The Chicago Landmarks Survey Database: Organized according to the city's 77 community areas, this inventory lists architecturally and historically significant pre-1940 structures in Chicago. Each section begins with a short history of the community, followed by a list of the significant properties identified in that area, searchable by building address. Each listing provides up to eight pieces of information, including: address, date of construction, architect, building style and type, survey ranking, landmark status, and identification number. It has a well developed and highly usable database.
Landmark Maps: Superbly organized maps and illustrations of historic areas.
Alphabetical Listing of Landmarked Buildings: Well, your house and my house probably won't be here, but the listing gives wonderful background for any neighborhood history study.
From the Chicago History Museum:
Building Permits Issued from 1898-1912: A database of The American Contractor for those years.
Criss-Cross Phone Directory for 1928: Criss-Cross directories are organized numerically by street and avenue. They are useful for identifying previous owners or occupants. (It is a very large .pdf file, which will be difficult to downlaoad without a broadband connection. Requires Adobe Reader.)
Photographs from the Chicago Daily News, 1902-1923: A wonderful and highly searchable group of pictures. Not much good for finding individual houses, but useful for major streets, parks, events and institutions. For example: the Hyde Park YMCA in 1905.
Chicago History Museum Collection Search: This database lists only about one-third of the actual holdings of the Society, but it is a start.
The Cook County Assessor's Housing Database: With this tool you can find any building in Chicago, its date of construction, square footage, estimated market value. And you can usually get a picture.
Field Guide to Chicago Area Buildings: An extensive bibliography of sources on the subject including libraries, museums, web sites and book.
Teaching History Through Architecture: University of Illinois at Chicago put together this excellent guide for teachers. There is plenty of material for the general researcher as well.