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Here are two sentences:

We're going to stop off in Denver for a couple of days before heading south.

He arrived in Athens on June 21, after stopping off at Frankfurt.

My understanding is that in the first sentence the settlement is meant, whereas in the second one only the airport, not the whole city, hence the preposition usage. Am I right?

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Correct! "At" a city if referring to a transit point (or in certain other specialized contexts like sporting events). "In" for neutrally expressing the city as the location of something.

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