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I want to buy a open jaw flight to South America. Bucharest - Buenos Aires at the beginning of January Bogota/Barranquilla/Cartagena(Colombia) - Bucharest, somewhere between 10 and 16 April.

When is the best time to buy them? Is it cheaper to buy them both on the same time or separately?

marked as duplicate by choster, Giorgio, Jim MacKenzie, CGCampbell, Thorsten S. Sep 7 '18 at 14:06

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    There is not really a single best time to buy any flight anywhere on any airline. See Flight tickets: buy two weeks before even during holiday seasons? – choster Sep 6 '18 at 15:36
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    It is a good idea to buy both legs on the same ticket in the same transaction. Aside from that, the best time to buy them is whenever they are cheap. But there is no magic time. – Calchas Sep 6 '18 at 23:04
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Unless you're travelling on budget airlines (which I assume you're not, since you're flying intercontinentally), it's almost always cheaper to buy any kind of return ticket, including open-jaw returns, than buy the equivalent sequence of single tickets.

Also, a significant advantage of return tickets is that the airline is contractually obliged to get you home if you have a return ticket. If you have two single tickets, they can take you to South America (fulfilling the contract of the first ticket) and then say, "Oops, we're terribly sorry but your flight home is cancelled. Here's a full refund." This fulfils the contract for the second ticket but leaves you stuck on the wrong continent.

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