Coming home to Chicago recently, we were landing just after some snow had blown through the area. We made a slightly unusual approach to Midway and did some maneuvering pretty low over the suburbs near the airport. I love this sort of thing since I find the rows of houses really fascinating from above. I managed to snap a few shots out of the window as we came in. These were grabbed with the camera on my phone so the control was a little limited but it was better than missing it altogether.
Some of the industrial buildings in the area also look cool from the air. This part of town has a bunch of rail yards and the geometry of them is impressive from above.