Congratulations to akn for being the first to correctly identify City #26. To date, no one has correctly identified City #25, so here is a hint – it is not in the Western Hemisphere.
Below is City #27, whose satellite image is turned somewhat askew. Good luck – I doubt this one will take long to solve, but in this image it bears a remarkable resemblance to another larger city several hundred miles to the west.
Source: commons.wikimedia.org
problogic
Panethos 
Chicago?
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Right region, but look eastward.
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Should have read your clue! I had the wrong Great Lake too, so I think I know what it is now, but will leave it for others 🙂
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Cleveland, methinks. Those of us who live in Chicago can be excluded for knowing it’s not Chicago. But I’ve always thought Chicago would be easy for anyone having studied Geography to recognize (or exclude), since it’s such a classic example of concentric patterns and the hub-and-spokes commuter railroad pattern.
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You are correct!
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