Long time lurker, first time poster. While doing a little genealogy work, I found that the houses my grandfather was born in (20th & Canalport) and later grew up in (18th & Union) were both torn down to make way for the Dan Ryan Expressway.
Does anyone know if any photos were taken by either I-DOT or City of Chicago of the various properties before they were torn down to make way for the expressway?
Not quite what you are looking for, but you might try www.historicaerials.com. Type in 18th and Union Chicago,IL. You can zoom in and see periodic updates of the area from 1938 on. It may show Grandpa's house, but no specific addresses, maybe a family member will have knowledge of the exact location. Ground zero of the image will be 18th and Union streets.
go to wttw website. last nite on this week in chicago this very question was asked. they have a link to highway construction pics of the time you are asking for.
Go to the Forgotten Chicago facebook group page and search the archives for NW construction photos. At least 5 in there. Plus, some Ike construction photos.