Watch a video that "re-creates" the Great Chicago Fire of 1871, from PBS, American Experience, Chicago: City of the Century.
The Chicago Historical Society in partnership with Northwestern University maintain an excellent site: The Great Chicago Fire and the Web of Memory. The site was given an excellent review in the Journal for MultiMediaHistory 1.1 (1998).
An excerpt from Karen Sawislak, Smoldering City, Chicagoans and the Great Fire, 1871-1874 (University of Chicago Press, 1995).
An excerpt from Carl Smith, Urban Disorder and the Shame of Belief: The Great Chicago Fire, the Haymarket Bomb, and the Model Town of Pullman (University of Chicago Press, 1994).
The Chicago Tribune hosts a topics page about the Great Chicago Fire of 1871.
There is a very brief entry by Karen Sawislak for the Encyclopedia of Chicago.
Vicki Beckam's interactive webpages: The Great Chicago Fire: A Webquest for Detectives.
Spoof paper The Onion relates sports news to the 1871 fire (January 25, 2007).