Up until March 30, 2003 it wouldn't have been uncommon to see small planes buzzing around the south side with the intentions of ultimately landing at Meigs Field Airport on Northerly Island. However, now it's not very common since Mayor Daley infamously ordered private crews to destroy the runway in the middle of the night, bulldozing large X-shaped gouges into the runway surface.
That's why we were surprised to see the shot above which was sent to us recently by a reader. Obviously the plane didn't land or take-off on the island, but it's still an interesting shot. We don't have much context about the pictures, but for the full reel check out this link.
If anyone knows more about these shots let us know.
(Hat Tip: MC)