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Hello. I would like to bring a cooler as a carry on to use once we arrive at our destinaton. Would either or both of these be acceptable sizes as carry on items? Can I carry on food items that do not require refrigeration in the cooler?
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I didn't get the graphic links, but I think this policy generally applies for size and content:
https://www.southwest.com/html/customer-service/baggage/carryon-bags-pol.html
Nothing specific about coolers, other than of course it shouldn't have any liquids in it when you go through TSA and it will need to fit in the overhead bin or under the seat in front of you once you board.
No restrictions on the food temperature either that I'm aware of, but it may be difficult to get a sufficient quantity of ice once you are airside in the terminal. Ice packs would be allowed by TSA if they are completely frozen.
Southwest doesn't serve meals, so you may want to put a sandwich in there for the flight!