A 1924 portrait is no longer in copyright. It is now more than 75 years old and is in the public domain. You do not need permission to reproduce it, and you cannot copyright it.
Chicago Portrait Company was founded in 1893 and located 509 South Wabash Avenue, Chicago, Illinois.Info from visitors: My photo is marked "The Studios of the Chicago Portrait Company. Located on...
You might need to use a time machine. The most recent reference I could find was 1932. The State of Illinois was trying to disallow the company's deduction of taxes paid to a foreign government....
I am also interested in the Chicago Portrait Company as I have an artist painting that has a plate on the back of the frame dated 1907 of my great grandparents. I am wondering if they had sales reps...