This one should be easy, right? It’s got a date and an opponent, and given that this is a long-ago photo, it has to be a pre-season exhibition game between the Cubs and White Sox.
Here’s the full photo:
That’s an old-fashioned Green Hornet Chicago streetcar; those vanished from Chicago streets in 1958, so it has to be from before then. The cars visible at the left are definitely pre-1950, so that winnows it down to a narrow stretch. The Cubs and White Sox played a postseason “City Series” off-and-on between 1903 and 1942.