Maps of Chicago from different time periods:
1834 - Chicago with the School Section and Wabansia and Kinzie's Addition
1849 - Rees and Rucker Map of Chicago and Vicinity
1857 - Map of Chicago (Blanchard)
1862 - Business Portion of Chicago
1868 - Blanchard Guidebook (before the fire)
1871 - Guide Map of Chicago
1871 - Map of Chicago Showing the Burnt District
1886 - Robinson's Map of Chicago (entire)
1890 - Chicago's Street Railways
1902 - Rand, McNally & Co.'s street number guide map of the principal part of Chicago
1910 - Rand McNally & Co.'s New Street Number Guide Map of Chicago
1921 - Map of Chicago and Suburbs
Collections of maps:
Current maps from the City of Chicago.
Maps at the Newberry
Chicago in Maps - A website with links to various historical maps of Chicago.
Fire Insurance Maps - Fire insurance maps show the footprints of buildings and other structures, as well as the construction material, use, and other information. This site contains a guide to fire insurance maps of Chicago.
University of Chicago Map Collection - Contains historical and current maps of Chicago.