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How to book free one ways on American Airlines flights to the Caribbean and Latin America

by on Wed May 6, 2015 • 7 Comments


We recently wrote about the hidden free stopover benefits of many cheap cash airline fares.

Most are for long international trips and 2nd tier destinations and airlines. But one of the more head scratching and useful ones comes from American Airlines.

Many American fares to the Caribbean and Latin America allow a free stopover in the American hub city you’re using to travel down there. And that opens up the possibility to add a free, or better than free ‘one way’ if you happen to live in or want to stay in an American Airlines hub city.

Here’s an example that gets you an extra one way to another city, but costs less than a regular roundtrip…

Chicago to Cancun prices at $509 for a regular roundtrip in January.

Screen Shot 2015-05-06 at 12.09.04 PM

But adding a leg to Washington, D.C. for Presidents Day weekend saves you nearly $100, and you get the same flights from Chicago to Cancun.

So if you were planning on visiting D.C. this is is a great way to save money both on your Cancun trip and on your D.C. trip. You can just buy a one way ticket back from D.C. or use miles to book the return.


Here’s another…

New York to San Juan – which prices at $403 roundtrip.

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But if you add an extra leg to Boston for Thanksgiving…the price actually goes down to $388…and you get to use the US Airways shuttle.


Yes, you’re getting paid to fly to Boston on this trip. And that one way from New York to Boston on its own would cost you over $200.

Basically, in order for the one way to come out free or better than free, the fare from your added city to your primary destination needs to be similar or lower than the regular roundtrip from your home base.

The fare example above is using half the roundtrip price from New York to San Juan plus half the roundtrip price for San Juan to Boston.

Here’s one that costs just a bit more than a regular roundtrip.

You can fly Dallas to Cancun for $469 roundtrip in January.


But you can add a one way to Denver in February for just $47 more and get a ski weekend on the same ticket.


Why does this work?

If you pull up the details of an American Airlines fare from the U.S. to the Caribbean or Latin America using the ITA Software Matrix (we talk about how to pull up stopover opportunities on ITA Software here) you’ll see that a free stopover is allowed in Miami, New York, Chicago, Dallas, Charlotte, Philadelphia, or Phoenix (basically any American Airlines hub). That stopover language means you can experiment with finding free or better than free one way legs to take you to an extra destination.

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It’s a really generous rule that we’re not sure will last, since it’s pretty well hidden, but easily bookable online. And it’s a benefit United and Delta don’t include on similar fares.

So to summarize…

  • You’ll find a free stopover in an American Airlines hub embedded in many American Airlines fares to the Caribbean and Latin America
  • That also means you can possibly add a free one way leg to somewhere else you want to visit
  • If the fare from the extra place you want to visit to your vacation destination is similar to the fare from your home base to your vacation destination, then you’ll end up with an almost free or better than free one way flight
  • It’s easy to search and compare using Google flights. Just open one window for your regular roundtrip search. Then open another window with a multi city search and keep changing the last city until you see something you like.
  • This tends to work best if you live in an AA hub city, and the fare from the ‘extra’ city to your Caribbean / Latin America destination is the same or lower than the fare from your home hub city to your destination.

It’s a great way to earn some extra AAdvantage miles and get one and a half trips for the price of one.



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7 thoughts on How to book free one ways on American Airlines flights to the Caribbean and Latin America

  1. TM

    I am trying to figure out the best way to go to PUJ and EZE this Christmas. Our home is LAX which is not an AA hub. Would it make sense to buy tickets as if we were in DFW, MIA or NYC? How would you do it?

  2. Kyle

    Other than the stopovers mentioned in this article, when booking a trip how do I know where to stop over to get this deal since we are all leaving from different airports?


      @Kyle – For all of the you need to have a stay in New York, Philadelphia, Dallas, Miami, Chicago, Charlotte, or Phoenix (the AA hubs). As for the city for the extra flight out of those cities…just experiment. Do a multi city search say..


      later date..

      PHL- (choose a city)


      @jimbabwe – It’s best if you live in a hub like New York.

      So you could for example do your winter vacation down in Aruba like usual. But on that same ticket tack on a one way New York to Boston a few months later to attend a wedding.

      So you’re stopping over at home in reality.

      For the way back from the extra leg, one ways are usually pretty reasonably priced for most domestic routes. Or just use cheap miles like Avios.


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