Chicago city directories can be found online, on microfilm, and in paper form. Below is a quick summary of some of the most convenient ways to access them.
Fold3.com offers Chicago city directories through 1923 but it doesn't include 1928/1929. It also has one distinct disadvantage: if there is more than one directory for a given year, the pages are intermixed. In other words, you may see page 1 from directory 1, followed by page 2 from directory two, followed by page 2 from directory 1, etc. This makes browsing a bit inefficient and it makes it challenging to correctly cite the images. You can use the site for free at Family History Centers or you can subscribe for home use. The path to the directories is Fold3 > Browse Records > Non-military Records > City Directories - Chicago.
Ancestry.com also has a collection of Chicago directories in a database titled U.S. City Directories, 1821-1989. You can search using keywords or you can browse by selecting the city and year from the drop-down menu. The dates cover 1839 to 1947, but be aware that some of the volumes, especially those after 1928, are business directories.
FamilySearch has put many Chicago directories online and they are easy to browse. The collection includes 1844, 1854-55, 1859-60, 1865, 1869-1901.
Chicago city directories are available at Cook County research facilities such as the Newberry Library, the Chicago History Museum, the Harold Washington Library, the Arlington Heights Library, and the Wilmette Family History Center and at libraries across the country that have large city directory collections. They can also be order in and viewed at Family History Centers. Check the Family History Library Catalog for availability.
The volumes researchers usually think of as "Chicago city directories" end with the 1928-1929 edition, but there are other directory resources available after those years.
Check Ancestry.com for directories after 1928. Their U.S. City Directories, 1821-1989 collection includes miscellaneous Chicago directories up through 1947.
The Harold Washington Library has telephone books on microfilm. Although they aren't as detailed as the early city directories, they can be useful in determining residence and address. Unfortunately, the quality of some of the films (tiny, out-of-focus print) makes some of the volumes nearly impossible to read. Check out Genealogy blogger Nick Gombash's inventory to see what's available.
Lurie index of people in Chicago in 1937 as well as all of the voters' registration for Chicago
This is a file card index available on FamilySearch microfilm. Cards appear to be arranged alphabetically by head of household but they also include others of the same surname residing at the address. The cards run up one side of the microfilm and down the other, so it's best to use these films on a reader that can easily rotate the images.
For other ideas, please see the "Specialty" tab.
Many specialty directories were published by professional, religious, and social groups. While they may not directly relate to individuals you are researching, they can provide important context. For example, the institutional advertisements in the early medical directories offer a glimpse into medical services provided by the various hospitals in Chicago in the early 1900s.
Chicago voter registration books for 1888, 1890, and 1892 are particularly useful because they include addresses along with information about length of residence, and year and place of naturalization. They are available on Ancestry, but can also be accessed through FamilySearch in Illinois, Chicago, Voter Registers, 1888-1892.
Coverage spans 1839-1928 but no directories are available for 1840-1842, 1918-1922, and 1924-1927.
The introduction to Polk's Chicago Directory 1923 provides a brief history of Chicago directories and a list of published volumes. You can find those pages on the Newberry Library's Chicago Ancestors website.
There are miscellanous directories available for later years—business directories and and criss-cross directories, for example. Check worldcat.org or search online genealogy sites for availability.
Newspaper research suggests that, at least in some years, the directories were canvassed in the spring and published in the summer. In 1874, for example, the canvass began on May 41 and was completed by May 17.2 The directory was on sale by June 213.
If the date of the canvass is important to your research, check newspapers for timeline clues.
1 "Wanted, A City Directory," The Chicago Daily Tribune, 3 May 1874, p. 16, col. 4; digital image, Newspapers Publisher Extra (https://www.newspapers.com : accessed 19 April 2017).
2 "Lakeside City Directory," The Chicago Daily Tribune, 17 May 1874, p. 9, col. 4; digital image, Newspapers Publisher Extra (https://www.newspapers.com : accessed 19 April 2017).
3 "Directory: Beware! Of Bogus Directories," The Chicago Daily Tribune, 21 June 1874, p. 9, col. 4; digital image, Newspapers Publisher Extra (https://www.newspapers.com : accessed 19 April 2017).
The directories generally list heads of household, including widows. Sometimes students or working women appear. The 1928/29 reverse directory listed spouse names.
The best way to answer this question is to explore the city directories that are available online, but here's a quick overview:
The format varies across years, but volumes are generally divided into three parts: front matter which includes information about government, civic, and religious organizations; an alphabetical section which primarily lists city residents who are heads of household along with their occupations, residence address, and possibly a business name and/or address; and a back section that lists businesses by specialty.
In addition, directories often include things like display advertising, train schedules, postal rates, and street and avenue guides.
Some volumes include unique resources. The 1923 directory, for example, has a lengthy history of Chicago.
The directories have many research-related uses. Here are just a few:
1) Names may be misspelled and/or they may be spelled differently from year to year.
2) If you're using Ancestry or Fold3, you can search by address. This approach can help you find people whose names are misspelled and it can sometimes help you locate friends or relatives who were living together.
3) Polk's Chicago (Illinois) Numerical Street and Avenue Directory for 1928/1929, a reverse directory (arranged by address) that includes spouse names, is available at chsmedia.org. Use this URL to navigate to the "A" section--http://www.chsmedia.org/househistory/polk/menus/polka.pdf and change "polka" in the address to navigate to the section you want. "polks" will take you to the "s" entries. The files are large and may take some time to download.
4) Widows are often listed as such, e.g., Anna (wid Thomas). These entries can sometimes be used to narrow a husband's death date.
5) Use the table of contents or check the first few pages of the alphabetical section to locate entries that were too late to be listed in the correct place in the alphabetical directory.
6) Online directory collections may include multiple directories within a year, often alternating images, which makes it challenging to determine which volume the pages are from.
7) A key to abbreviations may appear at the front of the alphabetical section.
Banner image created from Edwards’ Annual Director to the Inhabitants … in the City of Chicago for 1867 (Chicago: R. Edwards, 1867); digital images, Archive (https://archive.org : accessed 24 April 2017).
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