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I'm trying to book round trip flights from New Orleans to Havana, but there are almost no available return flights showing on the fare calendar. I know SW flies at least twice daily from Ft. Lauderdale and Tampa, why is there no availability for me from New Orleans?
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That is an annoying oddity you've found. Once again probably the result of some great programming on Southwest's system. Usually it's because the trip would require a layover that was too short, but in this case you could catch a morning flight from HAV to FLL then an afternoon flight FLL to MSY. I would suggest you find the best itinerary for yourself by searching for one way flights for each segment (HAV-FLL and FLL-MSY) and then call Southwest and see if they can make a valid trip out of it and give you a price. Definitely not ideal. Perhaps they could also offer a reason for you being unable to price it.