The Early Bird Check-In perk on the Southwest Plus & Premier Rapid Reward Credit Cards are counted per-person, not per trip or reservation from my understanding. Once you purchase Early Bird Check-In, you can expect to receive a statement credit on your next statement or the one after that crediting your card with the fees for Early Bird Check-In. Personally, I would recommend upgrading to the Rapid Rewards Priority Credit Card, as I think it gives you the most 'bang for your buck.' With the card, you receive a $75 travel credit, and you are guaranteed an A1-A15 boarding position which you can redeem 4 times (perk that is greater than $100 in value) compared to having a greater chance of getting an A15+ boarding position with the Early Bird Check-In perk. The points are also a good perk of the card which you can redeem for reward travel, and the card is able to move you up loyalty tiers faster with the possibility of earning Companion Pass. It does come with a greater annual fee, however, but I think that the benefits exceed the increase in the annual fee.
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