Glenn Ohrlin learned "I Used to Work in Chicago" in the late 1930's or very early 1940's according to this recording:


https://ia804702.us.archive.org/9/items/jack_horntip_collection_field_recordings/0918%20Discussion%20Of%20Learning%20%27I%20Used%20To%20Work%20In%20Chicago%27%20In%20The%20Late%201930s%20Perhaps%20Early%201940s.mp3

Field recording, Jack Horntip Collection. Recorded 8 Jan 2006.   Glenn Ohrlin (October 26, 1926 - February 9, 2015).