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Does Rapid Rewards ever offer challenges to get to A-List? It seems like I always end up at the end of the year with just a flight or two short of getting A-List status. I know I have taken part in challenges with other rewards programs to get me up to the next level...fly 8 legs in a month, etc.
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Yes, Southwest does occasionally offer challenges, sometimes for A-List, sometimes for a Companion Pass. They are usually very narrowly focused on specific markets, destinations, or a group of flyers that don't have any obvious similarities. I personally wouldn't count on getting a promotional offer before the end of the year so if you you're short a few flights start making plans to get a few extra in before the year is over.
BTW, the offers come via email and are also listed in your account online under the Promotions section.