Can I book a roundtrip flight with a visa that expires before the return flight? (I understand that I will have to extend the visa while there.)

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You can book a flight without having any kind of visa.

Airlines do not check that you have a valid visa when you book a flight, because lots of people choose to buy a flight before they get the visa.

They will check your visa when you board, and if you don't have a visa by then you will be denied boarding and not given a refund.

Whether you are going to get a US visa, or be permitted to enter the US with or without a visa will depend hugely on the state of Covid-19 at the time.

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