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I will be traveling with a friend who has back issues. She is hoping to take a pillow along to sit on. Will this count as a personal item?
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No since it will be held and will not go in storage overhead or under the seat in front of the passenger. It could also perhaps be considered a medical device? If this were Frontier you might have to worry about it, but Southwest won't care about a pillow.
--TheMiddleSeat