First, here’s a look at the full photo, which has quite a bit of detail of the Clark Street area surrounding Wrigley Field:
You can clearly see the rail line that used to run next to Wrigley, including a crossing gate.
The marquee says the Cubs were hosting the Phillies on May 3, 4 and 5, so it was a simple matter of finding dates that matched. The car is a clue, that’s a car from the late 1930s or early 1940s, and that’s exactly where I found the exact dates.