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Question about United "Carry-on bags" rules

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I haven't flown United in almost 10 years.

We will be flying on a domestic flight next month and want to only have carry on to avoid paying baggage fees. We are continuing on to Europe so we will each have a 9 x 14 x 22 inches bag [these will be checked for the European flight].

United allows "one personal item such as a briefcase, garment bag, laptop computer, purse or small backpack [from their website]" and "must fit under your seat or in the overhead bin".

I am trying to determine what would be allowed as the personal item. I have a fairly small "makeup bag" that will fit under seat but will it be considered too big? Do they really watch that personal bag for size? The bag is 8x8x14 and is softsided and can be squished if needed - about the size of a camera bag or a med backpack.

Must one piece go under seat or can they both go in overhead bins?

We will only have the one personal item, along with the 2 carryon bags.

Will these 3 pieces be allowed or do we run the risk of having to gate check?

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