Street nomenclature:

https://chicagology.com/chicagostreets/streetnames/

Street names (official list):

https://www.cityofchicago.org/city/en/depts/doit/dataset/street_names.html

Street design elements:

https://www.cityofchicago.org/dam/city/depts/cdot/StreetandSitePlanDesignStandards407.pdf

Suffixes in Chicago streets:

https://www.dnainfo.com/chicago/20160203/lakeview/only-1-of-chicagos-2582-roadways-doesnt-have-suffix-broadway

Standards for Treatment of Historic Properties (Secretary of Interior, generally incorporated in local ordinances and regulations, including Chicago):

https://www.nps.gov/tps/standards/treatment-guidelines-2017.pdf

Chicago Landmark districts, and dates of designations:

https://www.cityofchicago.org/city/en/dataset/landmark_districts.html