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NYC to way to go?

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We are older travelers. Fly business from NYC to Europe and beyond, but almost always use points. My points are on Amex or BA. Planning to go to Hawaii. Paying for business just too much money! So...should we fly to LAX or SFO, stay over (one or more nights) to break up the flight and then take the next leg with extra room seats.. Should we one way bite the bullet and fly thru with "extra room" seats? If we fly back from Hawaii and stay overnight at an airport hotel and take a morning (but not the first flight) can our luggage go thru without our getting it for the overnight. Suggestions wanted. United has good??

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