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The second you move abroad, you become a lot more popular! That far flung country looks a lot better to family and friends as soon as they know they’ll have a free bed and tour guide. My sister wanted to come visit me in Argentina in mid-May, so we set out to find her the best award ticket possible. Only one minor problem. As of two months ago, she had zero miles.

We ended up booking her a roundtrip from Los Angeles to Buenos Aires for a weeklong trip for 60,000 United miles. We even added a free oneway to Hawaii for next year for no extra miles and only $2.50 in taxes. This Anatomy of an Award should illustrate how to get from zero miles to a dream trip in two months, United free oneways, United’s hold policy, and the secret United award space open to United card holders.


In February, Megan told me she wanted to visit me in May. That’s not a lot of time to plan an award trip for someone starting with zero miles. To earn miles, she would need to:

  1. Apply for a credit card or two.
  2. Receive the card(s) in the mail.
  3. Meet the minimum spending requirement on her new card(s).
  4. Have the statement close and the miles post to her frequent flyer account.
  5. Book the ticket.

None of those tasks should take more than a few minutes of work on her end, but the lag time in receiving the card, waiting for statements to close, and waiting for miles to post meant that she would be cutting this close.

When she expressed interest in coming to visit, I did a quick award search to see whether United or American had better award space to Buenos Aires around the time she wanted to come.

Rookie Tip: Earn the right miles for the job.

United had great award space to Buenos Aires, and a United award would give her the best chance at scoring a free oneway to add on to her trip. United charges 60,000 miles roundtrip in economy class.

I suggested she apply for the United℠ Business Card

She had 56,500 miles, but a United roundtrip economy Saver award ticket costs 60,000 miles. She was 3,500 miles short.

When you are short 3,500 United miles, you have four choices, ordered from best to worst:

  • Transfer 4,000 Ultimate Rewards from your or your spouse’s account to your United account. She didn’t have an Ultimate Rewards card like the Chase Sapphire Preferred® Card, so this was impossible for her. Cost: 4k Ultimate Rewards
  • Transfer 4,000 United miles from a different United account to your account for a $60 fee. Cost: 4k United miles + $60
  • Buy 4,000 miles from United. Cost: $140.

We went for our best option. I offered to transfer her the remaining 4,000 miles that she needed. At $15 per 1,000 miles, the transfer cost $60.

Transferring miles from one United account to another is quite easy, though it does take about 48 hours for the transfer to be completed. You must also transfer them in increments of 1,000 miles, with a minimum transfer of 2,000 miles.

Rookie Tip: United holds–described below–last less than 48 hours. The transfer takes about 48 hours. If you are sure you will book something, make the transfer before putting your award on hold.

To transfer, you simply fill out the form, entering your information, the recipient’s information, and your credit card information. The miles disappear from the sender’s account immediately, and the recipient will receive an email when the transfer is complete.

Free Oneway

This trip is a perfect award on which to add a free oneway. Because Megan booked in April for a trip in May, she had 11 months after the main award to add a oneway trip somewhere else.

Rookie Tip: All segments of an award must be flow within one year of the award’s booking date. This includes free oneways.

We decided to look into adding a leg from Los Angeles to Hawaii in January 2014. This free oneway is a true free oneway–the main award costs 60,000 and adding the leg to Hawaii does not cost any additional more miles. This is because, according to United’s award chart, economy Saver award space costs 30,000 miles each way between Los Angeles and Buenos Aires, and between Hawaii and Buenos Aires.

Searching for United Space

When her miles posted, I went to and looked for award space. The situation was bleak, especially for economy class returns in the second half of May.

Saver returns are yellow or green. The second half of May doesn’t have many.

I signed into Megan’s account to double check her miles had posted. Then something funny happened when I searched the same dates again. Amazingly the amount of economy award space available increased dramatically.

The same search after signing in. Way more yellow and green.

The extra space appears to be an unadvertised benefit of having the United card that Megan opened. Scott was so impressed by the finding that he wrote a post about the extra space titled The United℠ Explorer Card’s Biggest Benefit?

With the extra space, we found a few different options, and settled on one that departed Los Angeles around 2:00 PM, stopped in Houston for three hours, and got her into Buenos Aires at 9:25 the next morning. The return was equally easy: depart Buenos Aires at 9:20PM, stop in Houston for an hour and a half, and return her to Los Angeles before most people her age are awake.

The free oneway would take her from Los Angeles to Honolulu eight months after her return from Buenos Aires.

She was excited, and I was excited, prematurely as it turns out.

We were able to put the reservation on hold using a neat trick that Scott taught me. After picking your flights, go through the reservation process.

You will eventually reach a section that asks for payment. You will have the option to pay with a credit card, or through PayPal. Select PayPal.

The United page will direct you to the PayPal page. When you arrive at the PayPal page, click the link to return to without paying.

Clicking on Change/View Existing Reservations along the top of will now show your itinerary held and give you the time the hold expires.

This trick only keeps your reservation on hold for a few days, so book the reservation as soon as possible. When reserving my sister’s ticket, we wanted to keep it on hold in order to allow the additional transferred 4,000 miles to post. Unfortunately, we had a bit of a setback trying to ticket the held reservation.


The award was supposed to be on hold until midnight PT last Saturday night. When Megan logged in to her account at around 9 PM, the reservation was no longer there.

I thought the simplest solution would be to re-reserve the same flights. Of course, when I did the search, only four of the five original flights still had economy Saver space. The initial leg, from Los Angeles to Houston, was no longer available.

Additionally, there were no alternate flights to Houston that day. The closest I could find was a flight from Los Angeles to Houston one day prior, which would leave Megan stuck in Houston airport for 20-something hours.

Since the dropped reservation was clearly United’s fault, I thought we might have some luck calling and speaking directly with United. I put the four flights that were still available (Hoston to Buenos Aires to Houston to Los Angeles to Honolulu) back on hold so that the space wouldn’t disappear and told Megan what to do on the call.

I had her call United and explain the situation to them. She told them that the computer had deleted her reservation prior to the cutoff time, and that one leg of her trip was no longer available but that she had the other four flights reserved again. When they told her there was nothing they could do, she asked to speak to a supervisor.

She told the supervisor that she knew that in special circumstances such as a computer error, United had the ability to solve the problem by manually opening up Saver award space on a flight. Additionally, she told them that I had transferred her 4,000 miles at a cost of $60 in order to book the trip. We hoped all these things would encourage United to fix the problem.

It didn’t work.

I was on vacation while all this happened, so we let the situation sit for a few days. When I got home, I logged into United and was met with great news: award space on an earlier flight from Los Angeles to Houston had opened up! I quickly reserved the space and called Megan, telling her to ticket the award as soon as possible.


After a pretty major setback followed by some good luck, Megan was finally able to book the trip online! The main award, a roundtrip from Los Angeles to Buenos Aires, routing through Houston on both the outbound and return:

And a true free oneway, from Los Angeles to Hawaii next year:

The whole award cost her 60,000 United miles, plus $83 in taxes and fees and $60 for the miles transfer.


I booked my sister a roundtrip award from Los Angeles to Buenos Aires for 60,000 United miles and $83.

Sometimes when booking awards, we run into technical glitches that can upend an entire hard-planned trip. Often, a call to the airline and a request to speak with a supervisor will correct the error. If this doesn’t work, stay calm and keep searching for space. Airlines are continuously opening up additional award space, and odds are you will find something that works if you have enough flexibility.

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