I would recognize my beautiful city no matter the focus. However, I don't think I would go so far as f/22, you would loose sharpness, but maybe f/14.
For future reference there is a spot just north of where you took this. At this spot, you get a great skyline shot from the north. This is not typical because most skyline shots of Chicago are from a boat straight west or from the south. Your close, about 15 minutes south of the spot I'm thinking of.
I know you like film, but could you provide the shooting specifications for reference please?
I love this city!
-Nick