Chicago City Directories
The 1923 Chicago Directory contains a publication history of the directories. "The Missing Directories" contains additional information. A representative number of directories have been digitized and are available here.
Street Guides
1866 1870 1875 1880 1885
1892 1900 1910 1923
City Directories
1866 1870 1871 1875 1880
1885 1892 1900 1910 1923
The Newberry holds a large print collection of Chicago city directories as well as directories from other locals. They are listed in an online guide.
Archive.org and Google Books contain more online Chicago directories (including social and business directories).