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Yes, It is actually quite easy. You fly in to one city, drive to another, and fly out of that city. If that is not what you are referring to, then there is the occasional city on a border of a country or state that has an identical on the other side of the border. This is most common with river borders, and flying into one city, crossing the border, and flying out of that city would also work.
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Earn +20 ptsQ: Can you fly into one city and out of another city?
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