Wow Adam, that picture of the car on the wall is in my neighborhood at the Cermak Plaza. The picture isn't actually that old. You can see the same view here in this google maps link. The owner of the plaza was an artist and had other car art there including the famous "spindle" or "car-kabob" piece.
Cermak Plaza
I am 99% sure that the view under that of the Sears store is in the same plaza. It would be interesting if it is because the plaza opened in December 1956. By the looks of those cars it looks like that era.