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Old Jan 20, 2023 | 11:37 am
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jsloan
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Originally Posted by DrunkenSailor
If you upgrade both segments on a connecting flight with PlusPoints, United will only charge PlusPoints once, at the same rate as the most expensive segment.

But ... what exactly is a connecting flight?
A flight with one or more transfers, but no stopover.

Originally Posted by DrunkenSailor
Tuesday
JAC DEN 6:09pm-7:39pm
Wednesday
DEN LGA 5:35pm-11:16pm

Why did I have to? Or asked another way, how would I have had to fly so that I only had to pay 20PP once?
You had a stopover at DEN. To be considered a connection, you would have needed to board a flight to your destination within 4 hours of arrival at DEN. You might have been able to squeak by with a longer transfer as long as it wasn't overnight. (The PlusPoints / luggage check-through calculation is less strict than the fare calculation).
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