How to Add a Free Trip to Hawaii Next Time You Book International Award Travel

A free trip is the best way to travel to Hawaii.

It’s been a long time since I’ve been to Hawaii.  In fact, I think the last time I was there was in 1996 when I spent several hours in the airport.  It had probably been 7 or 8 years before that when I actually spent time in Hawaii.

But I’m back.

This week I’m spending the week in Hawaii with my wife and three kids.

Today, I’ll let you know how we managed to book free tickets for our family of five to Hawaii.

How to Add a Free Trip to Hawaii Next Time You Book International Award Travel

In today’s post, I’ll be using American Airlines as an example, but you can also do the same thing with United.

When you travel from the United States to another country or you travel to the United States from another country, Hawaii is categorized as the same region as all the rest of the United States.  This allows you to add a stopover in or around your home city and make Hawaii your final destination at no extra charge.

Perhaps an example is the best way to illustrate this.

Back in May, our family traveled to Argentina.  We flew from San Carlos De Bariloche to the States.  We had some things we were going to do in Houston, and then we were going to fly up to Denver.  We could have booked a flight from San Carlos – Buenos Aires – Dallas (stop over) – Denver.

However, without adding any extra mileage requirement, we could (and did) book San Carlos – Buenos Aires – Dallas (stopover for two months) – Hawaii.

It doesn’t matter if you fly to Denver or Hawaii because they are in the same region in terms of the number of miles required.  Remember, if you are originating your travel outside of the US, you can fly to any part of the US with the same number of miles.

If you’re flying to Europe instead of flying back to your home, why not take a stopover in the closest gateway city, and then make Hawaii your final destination?  Go home for a few months and get back to the gateway city, and you’ll have a free flight to Hawaii.

If your whole trip is within the US, then Hawaii is considered a separate region, and it will cost you to add on a Hawaii leg (which still isn’t a bad deal).

We did need to find our own way to Denver and then back to Dallas, but since you can fly for 9,000 Avois round trip between Denver and Dallas, it was not a hard choice to go to Hawaii.

Free trip to Hawaii Details to Note:

  • On American, your stop must be in a US gateway city.  Since we flew Buenos Aires to Dallas, that was our US gateway city.  Our stop had to be there if we wanted to take one.  If you are flying international through Los Angeles, Chicago, Miami, or New York, that must be the place where you take your stop.  United does not have the same restriction.
  • You must complete your travel one year from your original booking dates.  Your ‘layover’ cannot last for more than one year from the time you booked the tickets.

Since we were planning on traveling from the States to Quito, Equador, we just applied the same free Hawaii trip in reverse.

Flights from Denver to Quito require the same number of miles as a trip from Hawaii to Quito.  So we just started our trip to Quito from Hawaii – with no extra miles required.

Thus, we’ve been able to add on a Hawaii stop with no extra miles (with the exception of getting from the gateway city home).

If you’re planning an overseas trip with either United or American miles, you might want to creatively think about how you can add at least a free one-way to Hawaii.



  1. Neil Jacobs says

    Can you book a a stopover flying from outside of the US to Honolulu (stopover in Dallas) on line or do you have to speak with a representative?

    • says

      You sure can. On the search page just click on “Redeem AAdvantage miles” and select multi-city. Just enter your flight to the gateway city as your first flight and then your gateway city (on a later date) to HNL as your second flight.

  2. John says

    I apologize but I am a little confused. I am trying to use United to book a flight from IAH to BZE and include HNL in the trip.

    Do I select “Multiple Destinations” and then do IAH to BZE, then BZE to IAH, and finally IAH to HNL? If I do this, the “Multiple Destinations” option does not provide me with the same “Saver Award” options for the IAH to BZE and BZE to IAH portions of the flight when compared to just getting a round trip ticket from IAH to BZE to IAH. As a result, I end up having to use more miles using the “Multiple Destinations” option.

    Am I not executing something within this correctly that is preventing me from using the same miles as a round trip ticket from IAH to BZE to IAH?

    • says

      When I did a search it showed IAH-BZE is 35,000 miles RT. IAH-BZE then BZE-IAH-HNL is 37,500. Thus, it may require an extra 2,500 miles to add on an HNL segment.
      What you’ll want to do is search each segment as a one way (IAH-BZE, BZE-IAH, IAH-HNL). Once you’ve got your dates available at a saver rate then you can search using the multiple destinations option. If you’re still having trouble tracking it down sent me an email (htcheap at gmail dot com) with your dates and I’ll see if I can help.

  3. russell says

    Great post. Can you please post the exact flight names/carriers for your entire trip? I am little confused at to whether you took United or AA on wich flights and on your outbound whether you went from Hawaii -> Dallas -> Quito or Hawaii -> Quito (which city was your stop over)?


    • says

      Thanks for the question. I can’t give the flights numbers as that would require a lot of work to go back and dig them up. However, all travel was on American (in my case).
      San Carlos De Bariloche, Argentina >> Buenos Aires >> Dallas //STOP (we had a 3 month stop over and flew on a separate ticket to Denver and bac) // Honolulu.
      On the return:
      Honolulu >> Dallas >> Miami // STOP (3 nights) >> Quito, Equador.
      Let me know if you have any follow-up questions.

  4. Juliana says


    We are planning to do go to from Miami to Buenos Aires and Bariloche in 2014 and I was wondering which airline you used redeeming miles all the way to Bariloche. I’ve been doing some preplanning but was not able to find an airline program that would take us all the way to Bariloche on miles, I can only find it to Buenos Aires.


  5. Mina says

    Mmm, newbie here, so please, bear with me.
    I’m coming back to LA after a trip to France. (flying with AA)
    So how can I add a free trip to Hawaii?
    I tried CDG-HNL-LAX but the segment HNL-LAX is not free.
    So what am I doing wrong?
    Thank you in advance to whoever can help me out

  6. CHRIS says

    Is this still workable?

    I’m not having luck with either AA or United. Flying from PTY (Panama City, Panama) to either DFW or IAH, trying to add on OGG (Maui).

    United is giving me an error message (“We were not able to find any available flights for award travel meeting your requirements. You may modify your search criteria or review the MileagePlus Travel Award Rules. If you need additional assistance, call 1-800-UNITED-1 (1-800-864-8331)”)

    AA is charging me 15K miles for each leg (30K total, one way)

    My gateway cities are flexible, as I will need to travel separately from/to my home airport.

    Any ideas, or have the airlines simply shut down this “bonus”?


    • says

      Sometimes the online systems is not as intuitive as the phone agents. I’d call American. For American it would need to be DFW assuming that is the city you’re flying to from PTY. I’d suggest a phone call with United as well.

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