May not be the right place - but traveling to Costa Rica in two weeks. Flying American on the way there and JetBlue on the way back. JetBlue apparently doesn't allow carry owns AND a personal bag. Only a personal bag that needs to fit under the chair. I've measured and it's not exactly the dimensions but it's close. What are the chances they actually measure?

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I think you should be fine. As long as you don’t over stuff it and it fits in the personal item bin before you board you’re golden. You can also try and out it in the overhead bin too so you have more leg room depending on space up too when you board :)

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