I found this photo from 1964 at Chicago-L.org, looking north along what is now the Red Line from above Buena Park:
Here's almost the same view yesterday:
So, a few changes. Two the west, three city blocks of apartments became Truman College in 1974. Wilson Yards and the Wilson Avenue Shop (the El structure in the center) burned down in 1994, replaced now by a Target and an apartment building. And all the trees have grown up.
Another thing: I found out more about how high I can take the drone. Generally, it's limited to 120 m AGL. But I can also take it up 120 m above any "structure" as long as I'm within 120 m of the structure. The flagpole on top of the Byline Bank is 58 m above the ground, meaning I could, with a quick adjustment to the drone settings, try taking it up to 178 m... Hmm...
Update, 40 minutes later: Yep. It'll go up to 130 m no problem in calm winds: