Did the title grab your attention? I’m actually underselling and overdelivering, since I’m going to show you how to get 3.5 vacations on two awards!

These free oneways that I’ve been writing about on United, Delta, and American are incredibly powerful. They allow you to get 1.5 vacations on one award. Logically that means you can get three vacations on two awards!

There are some limitations. First, one of the three vacations must be within the US or Canada, and chronologically you have to take this vacation second or third. The other two vacations must be international if you want to fly American or United, since free oneways are only available on their international awards.

With that out of the way, here’s how to plan three vacations on two awards. First figure out which airlines’ free oneways you can take advantage of. Any US-based flyer should be able to take free oneways on United. Flyers whose home airport is a North American International Gateway City for American or one of its partners can take free oneways on American. And flyers who live at an airport that handles through traffic on Delta can tack free oneways onto Delta awards.

Living in Los Angeles, I am lucky enough to be able to take advantage of all three, but that is not a requirement to be able to get three vacations on two awards. The only requirement is that you be able to get free oneways on one airline’s awards. Since we can all get free oneways on United awards, we can all get three vacations for the price of two! Pick two programs to use or one to use twice. I’ll make one United award and one American award.

Now pick your destinations. My international destinations will be open jaws to Stockholm/Copenhagen and Shanghai/Tokyo. My domestic destination will be Honolulu/Kahului. With United miles, I’ll book an open jaw coach award from Los Angeles to Stockholm and Copenhagen for the summer with a free oneway to Hawaii in the fall. Then with American miles, I’ll book an open jaw to Shanghai and Tokyo during spring with a free oneway from Hawaii to Los Angeles preceding the trip to Shanghai.

Here’s what the flying will look like with the type of miles used in parentheses–U for United and A for American.

(U) LAX-ARN in coach, August

(U) CPH-LAX in coach, August


(U) LAX-OGG in coach, September <— almost-free oneway

(A) HNL-LAX in FIRST, October <— free oneway


(A) LAX-PVG in FIRST, March

(A) NRT-LAX in off-peak economy, April


(A) LAX-HNL in economy, May <— free oneway


By combining the almost-free oneway that I tacked onto the United award to Europe and the free oneway I tacked on before the trip to Shanghai, I’ve got an open jaw trip to Maui and Oahu.

All that’s left is booking. The United award can be booked online as described in my post about Free Oneways on United Awards. Remember that on United, oneways to Hawaii are not free. On coach trips to Europe, they add 2,500 miles to the roundtrip price, so my United award priced at 62,500 miles instead of 60,000.

After finding space searching the oneways LAX-ARN, CPH-LAX, and LAX-OGG, I performed the multicity search and reserved the flights:

Had I chosen a business class return, the oneway to Hawaii would have added 7,500 miles. For 62,500 miles, I’ve got my first one and a half vacations.

Now it was time to find award space for my American award. This was also pretty simple since I wanted to fly direct routes that AA served. Why did I need to fly directly from Los Angeles to Asia? American only allows stopovers at the international gateway city. If I flew another routing from LAX to Shanghai, like LAX-SFO-HKG-PVG on Cathay planes, my international gateway city would be San Francisco. That would mean I could not stopover in Los Angeles. And I need my stopover at my home airport, LAX, to take advantage of free oneways.

I performed all of the American flight searches at once by using a multicity search at aa.com. All the steps of which were explained in my post on booking free stopovers on aa.com.

Remember that on American airlines, you can book a free oneway in both directions, so I decided to tack on a flight HNL-LAX before the trip to Shanghai and LAX-HNL after. The free oneways do not have to go to/from the same place. I could have just as easily booked the second free oneway to New York for example. After selecting all the flights, here’s what the itinerary looks like:

There are several things I want to draw attention to. First I hate American’s current international business class product, angled lie flat seats, so I won’t fly it. That left me options of coach or first class.

On the outbound to Shanghai, I chose to take advantage of first class, which is 67,500 miles oneway. That meant that my free oneway from Honolulu to LAX could also be in first class. Remember that American miles can be used to book from Hawaiian Airlines’ generous inventory, so I’ve selected a Hawaiian flight.

On the return, I’ve chosen to take advantage of American’s off peak coach pricing from Japan to the US. From October to April, you can fly oneway to Japan on AA for 25,000 miles instead of 32,500. (This discount also applies to partner awards and awards to Korea and Mongolia. Raise your hand if you’ve been to Mongolia.)

The free oneway I’ve added to Hawaii is interesting. It would not be convenient to wrap up a three week Asian vacation then only have five days at home in LA before going to Hawaii. But American airlines only allows bookings 331 days in advance, and April 15 is the last day available on its calendar today. However, American allows free date changes to flights and only requires that all award travel be completed within one year of the award’s booking.

That means that although I can only book today through April 15, I can actually fly that leg as late as May 19. The trick is to book a dummy leg now for any day, then when space opens up for a mid-May flight, I can call up and have the leg changed to the appropriate day for free.

OK, let’s take a look at how these awards combine into three and a half vacations.

Vacation 1– Europe

August 13, 2012 LAX to Stockholm in coach

August 22, 2012 Copenhagen to LAX in coach

Vacation 2– Hawaii

September 28, 2012 LAX to Maui in coach

October 7, 2012 Honolulu to LAX in first

Vacation 3- Asia

March 21, 2013 LAX-Shanghai in first

April 10, 2013 Tokyo-LAX in coach

Vacation 4– Hawaii

Scheduled 4/15/13, to be moved to 5/15/13: LAX to Honolulu in coach

Return yet to be purchased

The total costs of the three and a half vacations is 62,500 United miles, 92,500 American miles, and $177.80 in taxes and fees. Considering this includes a 14+ hour flight in a flying bed, and a first class flight from Hawaii to the mainland, this is an incredible deal!

I hope this one example of taking three vacations for the price of two awards has spurred you to consider how you can take advantage of this trick to stretch your miles! Let me try to anticipate some questions you might have about how you can exploit this opportunity.

Do I have to take three vacations in a year for this to work? No, if you want to take three trips in two years, here’s how to modify what I did:

May 2012- Book an award that has an international roundtrip in June 2012 and a free oneway in April 2013. Example: June 2012 MIA-LIM, LIM-MIA on LAN with AA miles. April 2013 free oneway MIA-EWR.

March 2013- Book an award with a free oneway that completes your second vacation, and book the main award for January 2014. Example: April 2013 EWR-MIA as a free oneway preceding MIA-IAH-LAX-SYD roundtrip on United with United miles in January 2014.

Now you have three vacations to Lima (2012), New York (2013), and Sydney (2014) that take place over two years on only two awards.

Do I have to take my free oneways to Hawaii? No, the free oneways can go anywhere the airlines’ routing rules allow. Those rules have been covered extensively in the posts I linked to at the top.

What classes, airlines, and destinations does this work with? This trick works in any class. It works on United, Delta, and American international awards, regardless of whether you fly those airlines’ planes or their partners’ planes. And this works whenever you can add stopovers to an award.

How will you get Stockholm to Copenhagen, Shanghai to Tokyo, Maui to Oahu, and back from Oahu on the fourth vacation? All my vacations are open jaws. I will use a combination of cheap paid flights ($50 inter-island), cheap Avios awards (7,500 Avios PVG-NRT, and 12,500 HNL-LAX), and trains (Stockholm to Copenhagen). It’s very easy to get between open jaw cities in general.

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