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Anatomy of an Award posts highlight real awards I’ve booked to show you the techniques needed to book your dream trip.

Recently the MileValue Award Booking Service had a client who was looking to travel to Costa Rica with his family of three in business class.

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This. Times Four. In Business.

Award bookings for three are sometimes a struggle, so I want to highlight an airline and some routes to Central America with fantastic award space for groups.

Even better the award presented an awesome opportunity to use United miles on a route that didn’t go up in price during the recent MileagePlus devaluation, and we got the client and his family a later “cheap one way” to Hawaii in First Class as part of the same award for only 12,500 miles extra per person!

  • How did I search for award space for three people traveling together in business class?
  • What airlines and routes have the best availability between the United States and Central America?
  • How did I add a discounted “cheap one way” to Hawaii, saving the client 82,500 miles on a future trip?
  • What was my workaround to the super-common error I got on

The client came to me with over 300,000 Ultimate Rewards and wanted three roundtrip business class tickets from Boston to San Jose, Costa Rica this summer.

This client was quite flexible with his dates although he preferred to travel over the Fourth of July holiday to minimize the number of days away from work.

He had heard about the recent MileagePlus devaluation and was worried he might not have enough miles any more. But luckily for him, award prices in the Western Hemisphere barely went up if they changed at all. Check the United chart here to see how much your desired award is.

Awards between the United States and Central America held steady at 17,500 miles each way in economy and 30,000 miles each way in business class.

The Search

The best miles between the United States and Central America are United miles because the Star Alliance has the most partners in Central America and best award space to Central America.

There are three United partners that serve Central America, and all are searchable on

  • TACA and LACSA (both part of Avianca) with hubs in San Salvador, El Salvador and San Jose, Costa Rica
  • Copa with a hub in Panama City
  • United with flights from its hubs to destinations throughout Central America

The best way to search for flights on is to search each direction separately. The more complicated the search you ask from, the worse the results the computer spits out.

I always start with a simple search of exactly what the client wants, moving on to more complicated segment-by-segment searching only if necessary.

Running a simple search between Boston and San Jose for three passengers gave us several options. I wrote down the flight numbers, dates, and cabins. Then I moved on to the return from San Jose to Boston and again wrote down the best options.

As you can see, availability in all cabins is excellent this summer between North America and Central America for three passengers in all cabins:

Award Availability

Copa Airlines had the best availability in both directions with the shortest travel time because of its direct flight from Boston to Panama with easy connections from there throughout Central and South America.

How did I add a cheap one way to Hawaii?

The legs of the main award were trivially easy to find. The client was looking at paying 60k United miles per person for roundtrip business class from Boston to San Jose, Costa Rica.

Since he hadn’t used a stopover or open jaw, though, I let him know we could do more by adding on a later free one way.

Free one ways are segments to or from your home airport that form half a different trip and cost zero extra miles. See the Intro to Free One Ways.

He said that his family had hoped to visit Hawaii at the end of the summer or early fall.

I knew that adding a later one way from Boston to Honolulu onto the award would be possible.

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Return from San Jose to Boston (red), then months later fly to Honolulu (blue). All on one award.

But adding the one way to Hawaii wouldn’t be free. Why not?

United charges 30k miles one way in business class from Central America to the mainland United States and Canada. United charges 42.5k miles one way, though, from Central America to Hawaii in business class.

If I added the flights to Hawaii, United sees the award as Boston to San Jose, then returning San Jose to Honolulu (with a free stopover in Boston). United would charge 30,000 miles for the outbound and 42,500 for the return or 72,500 total per person.

That means that adding the Hawaii flights in first class would add 12,500 miles per person to the price of the award. The flights aren’t quite a free one way, but they are a “cheap one way,” since a one way flight from Boston to Honolulu costs 40,000 miles on the United award chart.

The lesson here is that adding on a later one way trip to Hawaii usually costs a few more miles, but is usually way cheaper than booking that flight as a separate award.

Get on the Newark or Washington to Honolulu Flight

I hoped to route my client via Newark or Washington-Dulles to Honolulu as those two routes have a lie flat first class product, which I reviewed here. I isolated the direct Newark to Honolulu flight by choosing the non-stop button when running the search.

Award Search

I wasn’t holding out much hope as I know that this is a difficult leg to find award availability in business class on, let alone for three people, but I found three seats one day in September and asked the client if that worked. Those dates worked for him, and then I easily found availability on the Boston to Newark hop.

Booking the Award

Now that I had found availability that worked for the client, it was time to piece the entire award together. I used the Multiple Destinations award search on and entered:

  • Boston to San Jose
  • San Jose to Boston
  • (two months later) Boston to Honolulu

Quite often when trying to piece together three segment awards on, I receive the “Error” message immediately.


Luckily that didn’t happen this time. Unfortunately I got the other–sneakier–error that produces on multi-city searches:

The search results did not display the flight that I had found. This happens all the time that a multi-city search on doesn’t display all the results you find by searching one way at a time. That’s the exact reason we start by searching one way at a time, to see all the possibilities.

The solution is to choose whatever flights do display on at the Saver level in business class and move on. By securing the structure of the award (albeit not the exact flights), the system will save the mileage required, so that I can then call United (or have them call me) and swap out the dummy segments for the ones I actually want. Starting a reservation online also saves the client the $25 phone fee by mentioning to the phone agent that you started the award online and got an error and asking for a fee waiver.

I used to book a roundtrip award and then would call to add the “free” or “discounted” one way but I started to encounter significant resistance from United agents, so I now prefer to hold the outline of the award and just make changes.

This method doesn’t solve all the push back. I have spoken to agents who have told me that the award was priced incorrectly, so they cannot swap out flights since I’ve gotten such a “great deal.” As always, when I don’t get the answer that I’m looking for, I simply hang up and call back. This has served me well.

The final flights:

Award DetailsAward Price

The final award priced out to 72,500 miles and $52 per person. For that low price, each family member is getting 1.5 vacations with over 10 hours in a flat bed to Hawaii. Our client will have to book a separate one way award back from Hawaii or pay for a cash ticket.

What Star Alliance Airline Has the Best Availability to Central America?

In the past, I’ve seen as many as eight business class award seats on Copa Airlines flights, so if you are traveling with a large party, hopefully Copa serves your city! Copa serves many US cities directly from Panama, connecting all over Central and South America.

PTY map


I booked a client three roundtrip award tickets from Boston to San Jose, Costa Rica over the Fourth of July holiday. He also got three one way tickets from Boston to Honolulu in United’s lie flat business class seats.

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Return from San Jose to Boston (red), then months later fly to Honolulu (blue). All on one award.

A traditional roundtrip in business from the United States to Central America costs 60,000 miles. A one way from the continental United States to Hawaii in business class is 40,000 miles. This trip “should” have cost him 100,000 miles per passenger.

But by using his home airport as his stopover point, we added a cheap one way and his total cost was only 72,500 miles per passenger, saving him 27,500 per passenger.

Award Price

Despite United’s recent mileage devaluation, there are still deals to be had if you know where to look! If you encounter difficulty trying to do it on your own, hire the experts!

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