There are plenty of pictures of the Chicago skyline from across Lake Michigan.
I don't know when or how often that occurs, but here is a website that talks about it.
Chicago Skyline from Warren Dunes Across Lake Michigan
"This photo is really, really awesome because I think you're capturing some bizarre phenomenon. Theoretically, you shouldn't be able to see 60 miles away due to the curve of the Earth and your height. Even on a 200ft sand hill, your horizon should be 20 miles or so. But, I have heard that people in Michigan can sometimes see Chicago from the beach, which is just crazy."
--Link
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--Dave