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Taking Advantage of American Airlines One-Way Awards and Stopovers to Get Free Trips to Hawaii or Europe

If you’re willing to do a bit of advance planning of upcoming vacations, you can take advantage of American Airlines’ one-way awards and (limited) stopover options to really increase the value you’re getting out of awards if you live in one of their gateway cities. Let’s look at how this works:

We’re going to focus on American’s 40k mile off-peak coach awards from the US to southern South America (March 1 – May 31st; August 16 – November 30th) and from the US to Europe (October 15 – May 15th). This would also work with flights to Central America and to northern South America for 30k miles round trip (January 16 – June 14; September 7 – November 14th). Remember, American allows you to redeem one-way awards with a stopover, but the stopover must be in a gateway city. That means typically that you can stopover in New York or Miami for flights to Central & South America and in those cities and Chicago or flights to Europe.

Let’s say that you live in New York and want to do a trip in November to Buenos Aires, a trip to Hawaii in February and a trip to London in April. Instead of buying 3 round trips for a total of 125,000 miles, you would book the trip like this:

One-way award ticket JFK – Buenos Aires (20,000 miles)

One-way award ticket Buenos Aires – JFK – STOPOVER TIL FEBRUARY – Hawaii (20,000 miles) — the key here is that on awards from South America or Europe flights to Hawaii cost no more mileage than flights to the Continental U.S.. Also, even though it is an off-peak award for the South America – U.S., the connecting intra-US portion of the ticket DOES NOT need to be during off-peak time period.

One-way award ticket Hawaii – JFK – STOPOVER TIL APRIL – London (20,000 miles)

One-way award ticket London – JFK- STOPOVER – ANY DESTINATION IN US, CANADA, MEXICO OR CARIBBEAN for a future trip. (20,000 miles).

You’ve now spent only 80,000 miles PLUS you’ve gotten a one-way ticket to your next trip after your JFK stopover on the London return. Not too shabby. You can decide for yourself if you’d rather spend 100,000 miles for one roundtrip ticket in business class to South America, or if you’d rather use only 80k miles to fly to Buenos Aires, Hawaii and London.

Yes, this really only makes sense if you live in a gateway city (or can fly there cheaply), but it’s a pretty significant savings if you can book in advance. I’m happy to answer questions in the comments section.

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  1. How long can the stopover be? Wondering if one can use this if you don’t have more than one trip planned each year?

  2. So you’re saying that stopovers are sort of free. Coming back from Buenos Aires to JFK doesn’t cost anything.
    If I do this, would I need to book all the tickets in advance or can I go just book from JFK to Buenos Aires in November and come back to NYC. Then in a few months, book again, and etc?

  3. @CatJo American doesn’t appear to have specific rules about how long a stopover can be, but I can’t see how it’s a problem if it’s less than a year.

    @DanfromNY Stopovers ARE free as long as it’s in a “gateway” city — ie, a city where there’s a nonstop flight to the international destination.

    Coming back from BA to JFK isn’t free, the added JFK – Hawaii is the free part.

    You only need to book each one way with the stopover in advance. In my example above, you would only need to book, for example, Buenos Aires – JFK – STOPOVER – Hawaii. You could then book the Hawaii – JFK – STOPOVER – London later.

    • thanks! Does the same apply if I live in NYC? So I would start off from a gateway city. I checked from JFK to buenos aires and theres connecting flights so that wouldn’t count right? Sorry if this is obvious. I’m really new to flying.

      • @DanfromNY A little clarification: are you asking if you could stopover in JFK? I’m not sure what you mean by “wouldn’t count?”…

        • Okay I get it now. I got a little confused when you wrote, “For example, Buenos Aires – JFK – STOPOVER – Hawaii. You could then book the Hawaii – JFK – STOPOVER – London later.”
          I was thinking you meant Buenos Aires as your starting location and then flying to JFK because I live in New York so I would have to start from JFK to Buenos Aires.
          What if after coming back from Buenos Aires, I look for a JFK to Hawaii flight but find one that doesn’t fly nonstop to Hawaii but has 2 or more connecting flights to get there? Would that not qualify for the free stopover since it isn’t a non stop flight?
          Also, is there a special area on the aa website that only has “stopover” flights or do any flights work as long as it’s in the same time frame and city that you specified?

          • There is no JFK-Hawaii nonstops, but that’s OK. As long as the website (or the agent when you call) says JFK-ORD-LAX-HNL, for example, is a legal routing, then it will work.

            To book this your best bet is to call and speak with an agent. You can check the individual legs on, but I believe (correct me if I’m wrong) that you cannot book stopovers on the site.

          • thanks! are stopovers something that airlines don’t want people doing? So when I mention it to an agent, do I use that term or just try to book a qualifying flight?

          • Stopovers are completely legal on AA reward tickets as long as you are stopping in a gateway city. Some airlines allow no stopovers, and while AA has gotten more restrictive, this routing is completely legal. Just tell the agent you want a stopover in whichever city.

  4. worldtraveller2

    Even I am a little confused by this post. :shock:
    So, I get the one ways to get over there @ 20,000 each leg, but how about coming back? Do you book each one way back and if so, why didn’t you include this in your example? so return would be:
    EZE JFK STOP HON JFK STOP LON STOP CARRIBEAN? Can you do a whole lay out of actual trips like this with screenshots, so we, your readers, can see how this works in real time, real trips?

  5. I can certainly lay it out with screenshots, but the reason I broke it out as one-way trips above is because you should book them as one-way trips, not roundtrips.

    In the example I gave (and you quote above) the trip is not booked as EZE-JFK-STOP-HNL-JFK-STOP-LHR-JFK-STOP-Caribbean. That is 3 separate legs. You would book 3 trips:

    Trip 1: EZE-JFK-STOP-HNL. That’s a 1-way trip for 20,000 miles.
    Trip 2: HNL-JFK-STOP-LHR. That’s a 1-way trip for 20,000 miles.
    Trip 3: LHR-JFK-STOP-Caribbean. That’s a 1-way trip for 20,000 miles.

    ALL of the legs are one-ways. The initial leg does not have a stopover, but the rest do. You wouldn’t book a roundtrip.

    Does that make sense, or is that more confusing? I’m happy to lay out sample dates & flights if that makes more sense.

  6. Thanks for sharing this – it’s a great way to piece together 3 family vacations for only 320k miles plus some extra money for connecting ‘feeder’ flights for 2 parents and 2 kids!

    I checked and it works for me EZE – (any Hawaiian island) – Milan.

  7. worldtraveller2

    thanks for the clarification!

  8. hi, can this be done from sfo to paris then to hawaii..from american and united

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