How I Booked Patagonia and Thailand for $78.60!

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Have you booked award travel with miles and points? Then you know the thrill after you book that itinerary you’ve been dreaming of…all with points and miles!

I was able to take advantage of the United “cheap one-way” trick. (It’s now called the Excursionist Perk with albeit slightly less generous routing rules.)

United still has beneficial routing rules on roundtrip awards. 

You’re allowed 1 stopover and 2 open jaws.

stopover is when you stay in a location for 24 hours or more en route to your destination. An open jaw is when you fly to one location but depart from a different location.

The open jaw example below shows how you could depart from JFK in New York and fly to Santiago, Chile (SCL) and return to JFK by departing from Buenos Aires, Argentina (EZE).

It looks like an “open jaw” on the map.

open jaw
Example of an open jaw
Map generated by the Great Circle Mapper – copyright © Karl L. Swartz

Here’s what happened.

I decided to travel to Patagonia, a place I had dreamed of going for a while

I’d been eyeing up American award redemptions because of their off-peak, South American, 40k mile round trip awards available between March 1 – May 31.  

But, I waffled back and forth and the MileSAAver award flights disappeared.

Arrgh! Analysis Paralysis!

Torres del Paine
Torres del Paine National Park in Patagonia

I shifted gears to United even though a roundtrip award ticket to Santiago, Chile from New York would require 60k miles. I needed to use the one-stopover to maximize my miles and get the most value.

Plaza de Armas Santiago Chile
Plaza de Armas Santiago Chile

Since I planned to spend time in Southeast Asia during the summer, I wanted to book part of that flight on the same award ticket as my round trip to Santiago, Chile.

While I know the cheap one-way trick, and even the free one-way trick is legitimate, I was concerned I touched too many “zones” around the globe for United to consider my itinerary valid.

My plan was to go from NYC to Santiago, Chile. Then, Santiago, Chile to NYC. I would use NYC as my “stopover” and then continue on 2 months later to my “final destination,” Bangkok, Thailand. 

Putting the “stopover” at the end of my trip was fine because it is my home airport. I can easily “stopover” in New York for 2 months. 

view from Empire State Building NYC

I went to United’s website, clicked on multiple destinations in the flight search box, and began to piece together my itinerary. 

United’s website can be really helpful and easy to use while searching for award flights.

With each successful piece of my itinerary, I was feeling good. I found a Saver Award from NYC to Santiago and also from Santiago to NYC.  

But, I could only find Standard Award availability from NYC to Bangkok. 

Never book a Standard Award because the amount of miles needed is often double a Saver Award. I continued, though, because I wanted to see if the United booking system would allow this routing.

It worked! It said my itinerary would cost 130k miles plus a small amount of taxes and fees. I noted the system, not only accepted the itinerary but also discounted the number of miles.

Let’s break this down.

If I had booked the Saver roundtrip Award to Santiago alone, the number of miles would’ve been 60k. Then, if I had booked a one-way from NYC to Bangkok on a Standard Award, the miles needed would have been 85k.

Grand Palace Bangkok
The Grand Palace, Bangkok

I was never the best math student, but I know my itinerary should have cost 145k miles. The system created an itinerary 15,000 miles less because of the “cheap one-way” trick.

This told me the routing was ok according to United.

I went back and searched only a one-way flight from NYC to Bangkok to look for Saver Awards.  

If no Saver Awards come up when doing a round trip or multi-city search, you should always search one segment at a time to check again.

I did this and there was plenty of Saver Award availability on my travel dates. 

I noted the flight numbers, dates, and times, and called United to book because, again, the computer wasn’t showing the Saver Awards for the last piece of my itinerary, even though the awards existed.

customer service agent

I gave the United agent my flights from NYC to Santiago, Santiago to NYC, and the Saver Award from NYC to Bangkok.  The agent had no troubles and almost instantly said the miles needed for my itinerary would be 80k and $78.60 in taxes and fees.

The “cheap” one-way worked! 

The miles needed for a one-way Saver Award from NYC to Bangkok would be 40k on its own.  That meant, my itinerary would have needed 100k miles, if booked separately, and when added together with my round trip to Santiago.

I saved 20k United miles with this “trick.” Woo Hoo!

But even though I had confirmation the routing would work, I wasn’t entirely sure it would when I called United to piece together my itinerary.

I knew the computer let me book the routing with a standard award flight from NYC to Bangkok, but not with the saver award flight. I wasn’t sure if an agent would or could book it and exactly how many miles I’d ultimately need.

Aircraft at sunset

I had some miles in my United MileagePlus account and planned to transfer over the difference from my Chase Ultimate Rewards balance.

Chase Ultimate Rewards and United are transfer partners. These points transfer 1:1 between Chase and United.

Typically, I like to keep my points in a flexible program like Chase Ultimate Rewards to have more transfer options for future travel plans. I only transfer the points when I need them.

The United phone agent quoted my itinerary at 80,000 miles and $78.60 in taxes and fees. I explained I needed to transfer miles and asked if the itinerary could be put on hold, which the agent agreed to do.

The agent gave me a confirmation number and also emailed the itinerary to me, which showed all the flights, the mileage, and the taxes and fees. The agent explained I had until 11:59 pm of that day to call back and complete the reservation.

That’s where I made my first mistake.

closeup of a pecil eraser correcting a mistake

I shouldn’t have asked the agent to put the itinerary on hold. I shouldn’t have hung up.

What was I thinking?!

Here’s why.

First, I should’ve remembered Chase Ultimate Rewards points transfer to United instantly! I was so excited about my itinerary I momentarily forgot my booking process!

I should’ve transferred the points while I was on the phone with the agent. I am certain the agent would have seen the transfer and completed my booking.

Second, you never know what kind of agent will pick up the phone when you call back.

Let’s continue…

After hanging up, I quickly transferred the necessary amount of Chase Ultimate Rewards points to my United account, which transferred instantly. I called United back, gave the phone agent my confirmation number, and explained I needed to complete the booking now that my points had transferred.

From the moment she saw my itinerary, she questioned whether or not it was a legal routing.  She said she needed to get her supervisor.

Blood rushed from my face and formed a pit in my stomach. Now, this was going to take work. Ugh!

a woman in bed with her head laying on the computer holding her coffee mug.

That’s when I made my second mistake.

I should’ve simply hung up and called again. I could’ve called back for a different agent.  

But, the word “supervisor” made me nervous. What if my itinerary was flagged, making it obvious that other agents should question it, too.

I said OK and I was put on hold.  The phone call proceeded to go back and forth for over an hour.

The agent explained that her supervisor, as well as people in “other departments,” were checking the routing rules and the validity of my itinerary.

Finally, the supervisor came on the line and said the stopover needed to be in the middle of my trip. I knew this wasn’t true.

I’ve seen many examples of itineraries with a stopover at the beginning or end of a trip because of the need to be at your home airport.

I politely disagreed with her stating what I knew about stopovers.  She also discussed the “problem” of the different zones my itinerary touched. Yet, she could not state any specific rule that prohibited this routing.

She also asked if the booking agent had any trouble creating the itinerary, to which I answered no because the mileage he quoted was stated instantly after he entered the final flight details.

I continued by saying I would never have transferred the miles over had I thought there would be a problem and I was ready to use my United Explorer card to pay the taxes and fees.

Hold again….

Just like that…I mean an hour later, the supervisor came back on the line, completed the reservation, and ticketed me! 

The itinerary did not change, nor did the number of miles or the amount in taxes and fees.

What does this mean for you?

You can get incredible value from your miles and points when you take advantage of any stopovers and open jaws allowed by your airline.

Whether you add another city to your vacation or add a one-way to the beginning or end, there are interesting opportunities to consider and value to maximize.

Also, if the airline agent on the phone is knowledgeable, do everything possible to get your itinerary booked with that person. This is especially true if your itinerary takes advantage of stopovers, open jaws, or tricky multi-city bookings.

Even though United’s rules have changed since this booking, this guide of the best ways to use your United miles can help! 

Have you used United’s stopover and open-jaw rules to maximize your award bookings?

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4 thoughts on “How I Booked Patagonia and Thailand for $78.60!”

  1. I enjoyed reading your post. However, I’m a bit confused how your SCL-NYC qualifies as an excursionist perk because it doesn’t start/end in the same region (Mainland US vs. Southern S. Am).

    1. Jackie Sills-Dellegrazie

      Thanks for reading, Kay. You are right. I took this trip before United officially called it the Excursionist Perk. Previously, it was a similar benefit with the free one-way, however, it didn’t have the same region rules as now and it could also be added to the end of a trip as opposed to now only sandwiched between 2 other segments.

  2. Thanks for clarifying! Bummer that they changed the rules. I was trying to figure out some creative routine myself (Have a RT SFO-LIR) trip in April and then a OW CUN-SFO in July (outbound trip on another carrier). I did all those with miles and was trying to squeeze out another leg for “free” somewhere but not sure if that can be done with what I have. Everything I try to tack on/add in just codes as another segment, with nothing free.

    1. Jackie Sills-Dellegrazie

      Ugh, I know! The rules were better before but I still find value in the current Excursionist Perk. I have a guide about using United miles for this perk If you currently have bookings, you won’t be able to add to them. Also, there is a key part of the Excursionist Perk, your itinerary must end in the region it started in. That’s one of the reasons why my example in this article doesn’t work anymore. You can’t start in the US and finish the itinerary in Thailand. Take a look at that guide and let me know if you have any questions.

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