Revealed: An Insane Use of The United ‘Free’ One way (Part 1)

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I’ve called my next trip report The South America, Europe, Africa Heist. Allow me to explain why. Initially, I tried to book a flight on Delta to Mt. Kilimanjaro. That was a sham. Then I booked a United flight to Kili on Turkish for 80k. I was feeling proud of this decent redemption until a reader told me that I didn’t push it far enough. He said I was not taking advantage of United’ Free One Way. I tried to read blog posts about unlocking the ‘free one way’ but was confused by the explanations. Trading dozens of emails, I learned how it works. In this post, I will try to break it down by showing you a stupendous itinerary that I booked. In all, I will fly 37,979 miles (mostly in business) for 95k Delta points and 105k United points.

map distance

Let’s get to it:

The Free One Way is the result of booking three Flights: Flight #1, Flight #2, and Flight #3. The ‘free’ flight is Flight #2. Here’s how I triggered it.

Flight #1: Found Flight #1 from USA to North South America for 35k in business. North South America, per United’s website, includes Colombia, Ecuador, French Guiana, Guyana, Peru, Suriname, and Venezuela.

Flight #3: Found Flight #3 from USA to USA (could be anywhere in Mainland US, Alaska & Canada) 11 months out in coach for 12,500. (I’ll get to why it is USA to USA and why it is in coach in a moment).

Flight #2: Found Flight #2, the ‘free’ flight from Central & Southern Africa to Central & Southern Africa in business. That flight would be 30k if it was booked separately.

The total for three one ways would be 77,000 without the ‘free’ one way but United provides the free perk if you book the itinerary as a multi-segment.

Here’s the breakdown:

  • The purpose of Flight #3 is to trigger the ‘free’ one way. If you book Flight #3 you can fly anywhere within one region on Flight #2. Flight #3 has to originate and conclude in the same region as Flight #1’s origin. Here, I went from USA to North South America. Therefore, Flight #3 also has to go from USA to USA. Since my primary goal was to get Flight #2 as cheap as possible, Flight #3 is in coach.
  • For Flight #2, you want to find the most expensive points flight within a region. MileValue has a tidy chart showing the requisite miles. Central & Southern Africa to Central & Southern Africa is 30k as is Mexico to Mexico, Central Asia to Central Asia, and the Middle East to the Middle East. It makes the most sense to reserve Flight #2 for Central & South Africa because it is cheap to get around Central Asia and Middle East using cash.
  • I chose Flight #1 from USA to North South America because it was the cheapest way to get to South America on points. From there, I can easily get to Brazil and utilize this perk again on the way to Africa. (That explanation will be in a future post.)

So how do you book it? As I stated above, I found Flight #1, 2, and 3 separately. Then I used the multi-city award booking tool and looked for those exact flights. Unfortunately, I celebrated too early because the ideal routing was not available in multi-segment mode. United’s itinerary spews out what it thinks is ideal and there’s nothing you can do about it online. Though it was not the ideal routing, I made the reservation and prepped myself for The Award Ticketing Game: Call Center Roulette i.e., calling United until I found an agent that could book my perfect itinerary. It took multiple calls, cancelling then rebooking, calling in again, until I finally received the ideal routing which was LAX-BOG on a the Dreamliner.

Part 1’s grand total is $121.22 and 47,500 United miles. 

If you think that was impressive, check out Part 2.

23 COMMENTS

      • But yes, you could. Or you could start your trip in Hawaii and do inter-hawaii flight as the throw-away and get more value but that means you’ll be in hawaii to start

    • So what i did was book Montana to Detroit for Thanksgiving. I live in Montana part time (long story) and the flight out of here is literally $800 and thanksgiving? forget about it.

  1. It’s not RTW itinerary. It is in fact round-the-Atlantic – please correct in your references.
    Will see how the whole story unfolds…

  2. I’m very interested to see how this progresses, as the lady friend and I are quitting our jobs and traveling the world for at least a year in Sept, and South American and Africa will be the first six months or so of our travels. I’ve been studying up on this free one way for months, trying to figure out how to best use it. I assume there wouldn’t be any problems with United if you booked multiple itineraries like this, but with Flight #2 on Itinerary 3 happening before flight #3 on itinerary 1, for example? If my plans work out, I would envision ending up with like half a dozen ‘Flight #3s’ in the US (or northern South America), but all over a year down the road.

  3. I forgot to ask my other question. Do you think it’s possible to book the three flights, but then change Flight 3 to a date earlier than Flight 2? Would a United agent realize that Flight 3 was linked to that ‘free’ Flight 2? I haven’t seen this mentioned anywhere.

    • I get your strategy but I wouldnt do it. I tried to make a change during the process after my itinerary was almost complete. I spoke to an agent who said the whole thing was illegal and this and that (even though it wasn’t). I got what I want and I’m not going to push it and lose it all.

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