These photos were purchased together and are in identical paper frames with a title “Memories of Chicago’s world-famous college inn.” One photo has a name written in ink above it: Ivan V. Wray about 1943. The photo of the woman simply says “about 1943.” I first did a search in the tree at FamilySearch.org for Ivan V. Wray. I found an Ivan Volney Wray, born in Winfield, Kansas in 1899 and died in Washington State in 1964. I will start there and message a contributor of that profile to see if this is the correct Ivan V. Wray.
UPDATE: Wow, this was the quickest mystery solved. Within 30 minutes of uploading the pictures and emailing the FamilySearch.org contributor, I received confirmation that the two photographed are her grandparents. Ivan’s wife’s name was Esther. These photos are heading out in the mail to Cynthia in Irvine, CA.
Another happy return!