A Helpful Resource for Free One-Ways with the New United Award System

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I need to start off this massive post by saying that none of this would have been on my radar had I not been a long-time follower of Drew Macomber over at www.travelisfree.com. His content is unique, creative, and refreshingly short on sale tactics. My goal for this post is to explore and expound upon his recent discovery that, when United recently devalued its awards through changes to its booking system, it simultaneously opened up new opportunities for savvy miles and points enthusiasts in 2016 and beyond.

Use these links to jump to the section you want to explore:

Section 1: The basics of the new free one-ways loophole with United Miles

Section 2: Guidelines to increase redemption values

Section 3: Nesting multiple itineraries to create savings in economy and business

Section 4: The longest flight segments for free one-ways sorted by region

Section 5: Known limitations of the new United free one-ways loophole

Section 1

The basics of the new free one-ways loophole with United miles

Basics of the New United Free One-Way Opportunity

When United changed its booking rules on October 6th (2016), it closed several loopholes in the system, including one that allowed for adding "free one-ways" to the beginning or end of flights. This loophole was reliant upon United allowing a free stopover on any international award flight. While this is no longer possible, the new rules stipulate allow for an excursionist segment. It turns out that this segment can be anywhere in the world besides the ticket origin and it must remain within one region, as designated here.

To simplify as much as possible, what Drew discovered is that you can essentially book any two one-way tickets that begin and end in the same region (even two domestic flights), and then stick any one-region segment you like in the middle at no extra cost. Even better, booking a premium seat on the first leg of the ticket will make that excursionist leg premium also, and at no additional cost.

Minimal Point Outlay for Maximum Free Flight Hours

One way to maximize the benefits of this loophole is to book the cheapest first and final segments, so that the relative value of the free one-way stuck in the middle is higher. For example, one of Drew's readers from Hawaii commented that he could book an inter-island flight for 6,000 MileagePlus Miles.

If you happen to live in Hawaii or need some inter-island flights as part of a vacation there, that means you can spend as little as 12,000 miles to earn a free segment in another region that might normally cost as much as 20,000 miles. You can do even better by booking a business or first class inter-island segment (8.5/10k each way), which should make the free one-way a free premium class flight!

Assuming most people won't be able to take advantage of the inter-island flights, the next cheapest are domestic US flights on United metal that are less than 700 miles between city-pairs. These flights cost just 10,000 miles each. Doing this, you'd pay 20,000 miles for a pair of shorter domestic one-ways and receive a free one-region segment in economy that could be more than twice as long as the two domestic flights combined.

Section 2

Guidelines to increase redemption values

Booking an all-economy award with a free one-way

When booking an all-economy class United award, the best way to maximize the value of the free segment (based on percentage of miles saved) would follow these rules:

  1. Make the first and last legs (the segments you'll pay for with award miles) as cheap as possible. For example, inter-island flights in Hawaii are 6,000 miles each, flights within Japan are 5,000-8,000 miles each, and US domestic flights less than 700 miles in distance are 10,000 miles each. In these scenarios, you will pay between 10,000-20,000 miles for two one-way tickets and receive a third one-way in any other region in the world for free.
  2. While your "paid" award segments might ideally be short, you'll get maximum free flight-time by making your free segment in the middle as long as possible. Try for flights that cross the entirety of a region, such as Los Angeles to New York or Reykjavik to Istanbul. You can reference my resource post to learn about some of the longer one-region free one-ways.
  3. In a similar fashion to rule #2, if you want to maximize value, you would also want your free segment to be in a region that typically charges more for flights within that region, such as the Middle East (20k within the region). The Africa regions, South Asia, and Australia/New Zealand are also high-value options (17.5k within the region).

Booking an award to receive maximum free business/first class air-time

Selecting a business class flight as your first segment will allow you to book your free one-way as business at no additional cost. In this case, you'll benefit from a different set of rules than with all-economy awards:

  1. Make the first leg as long as you want, since there are no short-distance discounts for business-class award options.
  2. Try to fly the first leg in a relatively cheap United business class region and then fly the free one-way segment in a relatively expensive region for business class.
  3. Try to make the first leg a transcontinental or other longer flight within one region to get a better business class product.

Section 3

Nesting multiple itineraries to create savings in economy and business

Nesting Two New United Free One-Way Bookings in Economy Class

First, you'll need to do some date-selection, because once you know your flights, they will be intermingled between two separate bookings that will have date overlaps. In the example below, Booking #1 has the first leg of what will be a free roundtrip between Bogota, Colombia and Lima, Peru, but Booking #2 has the first flight you will actually take.

  • Booking #1: LAX-PTY (17.5k), BOG-LIM (free), SFO-EWR (12.5k)
  • Booking #2: Any domestic economy flight (12.5k), LIM-BOG (free), EWR-SFO (12.5k)

Combining these two bookings in the order they would be flown results in a one-way from San Francisco to Panama City (with an optional stopover in Los Angeles), a round-trip between Bogota and Lima, and a roundtrip between San Francisco and Newark.

  • Combined: SFO-LAX (10k), LAX-PTY (17.5k), BOG-LIM (free), LIM-BOG (free), SFO-EWR (12.5k), EWR-SFO (12.5k) = 52.5k United miles
  • Booked Separately: SFO-PTY (17.5k), BOG-LIM-BOG (20k), SFO-EWR-SFO (25k) = 62.5k United miles

The result of nesting two United bookings such as these allows the traveler to utilize the new United free one-way loophole to save 7.5k miles + add a free flight anywhere in the US. You can see this as an approximately 12% savings + a free flight or a 30% savings if you convert that flight to miles, but it is contingent upon several things:

  1. A nesting strategy like this is complicated enough that some people could get tripped up...focus will be required to make sure all the dates are correct and that it all prices out right.
  2. There must be a desire to book these routes anyway (i.e. saving 10k doesn't help if you didn't want to go to all of these places anyway).
  3. There are still open legs in these routes, such as the return to San Francisco from Panama City if you want to create three distinct trips, or the flights between PTY-BOG and BOG SFO if you want to make two trips (long multi-stopover trip to Latin America + transcontinental flight between San Francisco and New York City)

Nesting Two New United Free One-Ways in Business Class

Achieving greater savings on free one-ways through business class is one of the tricks I pointed out in Section 1. Since there is no additional benefit to booking business class on the final leg of either booking, I will show examples with two legs in business and the third in economy class, which maximizes the best discount by percentage of total cost.

  • Booking #1: SFO-PTY (30k), BOG-LIM (free), EWR-SFO (12.5k)
  • Booking #2:  EWR-SFO or any domestic biz flight (25k), LIM-BOG (free), SFO-EWR (12.5k)
Booking #1

Booking #1

Booking #2

Booking #2

Combining these two award bookings in order of date flown results in a one-way biz class flight from any two cities in the US, a one-way flight biz class from San Francisco to Panama City, a roundtrip biz class between Bogota and Lima, and an economy roundtrip between San Francisco and Newark.

  • Combined: EWR-SFO (25k), SFO-PTY (30k), BOG-LIM (free), LIM-BOG (free), SFO-EWR (12.5k), EWR-SFO (12.5k) = 80k United Miles
  • Booked Separately: EWR-SFO (25k), SFO-PTY (30k), BOG-LIM-BOG (40k), SFO-EWR-SFO (25k) = 120k United Miles
  • Booked only in economy: EWR-SFO (12.5k), SFO-PTY (17.5k), BOG-LIM-BOG (20k), SFO-EWR-SFO (25k) = 70k United Miles

In this example, we get the six-hour roundtrip between Colombia and Peru for free in business class on a nicely outfitted Avianca A330! This amounts to a savings of 40k miles or a 33% savings versus booking the same flights without the new free one-way loophole. Another way of looking at it would be to compare with an all-economy booking. For just 10,000 more points, you get up to 19 hours of business class air-time and it's sometimes easier to find business class space on busier flight dates, so this helps with booking availability, too!

Section 4

The longest flight segments for free one-ways sorted by region

Mainland US, Alaska & Canada

The best plays for this region include the longest flight Anchorage-NYC at about 7hrs in the air (though most flights between the city-pair involve a connection through Denver) and the big transcontinental routes. Pairing Newark and LAX or SFO will likely produce the best results if you're looking for a premium product on transcon flights with United (if you want to know what that looks like, check out this review).

  • Los Angeles-New York City: 2,451 miles on United
  • Los Angeles-Boston: 2,608 miles on United
  • Los Angeles-Washington DC: 2,286 on United
  • Los Angeles-Montreal: 2,471 miles on Air Canada
  • San Francisco-New York City: 2,561 on United
  • San Francisco-Boston: 2,700 miles on United
  • San Francisco-Washington DC: 2,439 miles on United
  • San Francisco-Montreal: 2,535 miles on Air Canada
  • Seattle-New York City: 2,398 miles on United
  • Seattle-Washington DC: 2,303 miles on United
  • Seattle-Toronto: 2,057 miles on United
  • Anchorage-New York City: 3,364 miles on United
  • Anchorage-Chicago: 2,841 miles on United
  • Anchorage-Denver: 2,403 miles on United
  • Anchorage-San Francisco: 2,017 miles on United


The longest non-stop flight of significance that I could find was between Moscow and Lisbon coming in at round-about 5hrs of flight time. Another interesting play for Europe would be using Lufthansa hubs in Germany or Scandinavian's hub in Copenhagen to connect Reykjavik, Iceland to a number of Mediterranean destinations. Check out the sample below:

Reykjavik to Istanbul via Copenhagen is be 7:20 of flight-time. Using two flights in the US to bookend this award ticket makes the Europe part show up for free, creating a free one-way! Even after recognizing that no miles were charged for the intra-European flights, you might be wondering why this award shows up as 22,500 miles instead of the 25,000 two one-way US flights usually costs. Since Newark to Baltimore is a short flight, United offers it for 10,000 instead of the usual 12,500 each way.

Perhaps the best part about this award came when I switched the LAX-EWR leg to BusinessFirst for 25,000 miles. When I did that, I was able to book the 7+hr European portion in business as well, without incurring additional miles or tax charges. That means that I can fly nearly all of this route in business class for just 35,000 United miles.

Here are some of the city-pairs for Europe I found interesting:

  • Lisbon-Copenhagen: 1,537 miles on TAP
  • Moscow-Lisbon: 2,433 miles on TAP
  • Moscow-Geneva: 1,503 miles on SWISS
  • London-Istanbul: 1,546 miles on Turkish
  • London-Athens: 1,509 miles on Aegean
  • Reykjavik-Munich: 1,674 miles on Lufthansa
  • Munich-Rhodes: 1,169 miles on Aegean
  • Reykjavik-Frankfurt: 1,493 miles on Lufthansa
  • Frankfurt-Istanbul: 1,159 miles on Lufthansa

Northern South America

Last I was aware, Avianca flies mostly their A330 aircraft from Peru to Colombia, which is a solid offering for these 3.5hr flights. If one were combining travels through Central America and/or the Caribbean with Northern South America, one of these free segments could be tacked on to two flights in those regions for a total cost of 20,000 United miles in economy, or 30,000 miles if you want to fly the front end + the free one-way in business.

You'd still have some connecting flights to book, but this works out to potentially 10+ flight hours in business and an additional domestic flight in economy for for a very low rate. Most normally-booked business class flights of 10+ hours (think US-Europe or US-Southern SA) cost at least 55,000 miles each way, instead of only 30,000 here for the same amount of air-time.

  • Lima-Bogota: 1,175 miles on Avianca (see my "latin sampler" post for an example using this segment)
  • Lima-Medellin: 1,267 miles on Avianca
  • Cusco-Bogota: 1,270 miles on Avianca
Avianca A330 Business Class Seats

Avianca A330 Business Class Seats

 Southern South America

While Southern South America doesn't offer many long flights, the routes I did find happen to be "5th Freedom" flights. This means that for your 1.5-2hr flights, you'll be flying an aircraft that's meant to go long-distance, so the quality of the seats and service is likely to be higher.

  • Santiago-Buenos Aires: 709 miles on Air Canada
  • Santiago-Sao Paolo: 1,071 miles on Turkish Airlines

Central America

  • Panama City-Belize City: 838 miles on COPA
  • Panama City-Guatemala City: 845 miles on COPA
  • Panama City-San Salvador: 722 miles on Avianca

South Asia

The longest practical free one-way I have found in the South Asia region would involve flying on United partner Singapore Airlines between Hong Kong and Bali via Singapore. This combo would be over 2,600 miles of flying and would result in a savings of 20,000 United miles in a high-end economy seat or 40,000 miles in a very solid business class product for a medium-haul flight.

  • Hong Kong-Singapore: 1,595 miles on United or Singapore Airlines
  • Hong Kong-Phuket: 1,429 miles on Thai Airways
  • Hong Kong-Bangkok: 1,051 miles on Thai Airways
  • Bali-Bangkok: 1,840 miles on Thai Airways
  • Bali-Singapore: 1,040 miles on Singapore Airlines

Australia/New Zealand/Tasmania

While United flies from the US to Australia and New Zealand, flights within this region will be on Air New Zealand. Air NZ opens a decent amount of economy award space, but very little in business class, so although you can get some decent-length free one-ways, the larger benefit of business class award bookings is unlikely. 

Auckland and Perth stand out as a city-pair with serious potential, but the 7+ hour flight is 17.5k United miles normally and, unless you were planning to go to Perth anyway, doesn't offer much utility.

  • Auckland-Perth: 3,320 miles on Air New Zealand
  • Auckland-Sydney: 1,343 miles on Air New Zealand
  • Auckland-Melbourne: 1,641 miles on Air New Zealand
  • Auckland-Brisbane: 1,428 miles on Air New Zealand
  • Christchurch-Brisbane: 1,553 miles on Air New Zealand
  • Christchurch-Sydney: 1,323 miles on Air New Zealand
  • Christchurch-Melbourne: 1,501 miles on Air New Zealand
  • Queenstown-Sydney: 1,206 miles on Air New Zealand
  • Queenstown-Melbourne: 1,335 miles on Air New Zealand

Section 5

Known limitations of the new United free one-ways loophole

Limitations of the New United Free One-Ways

  1. The region of origin must be visited twice for the itinerary to be eligible for the excursionist perk.
  2. The free one-way must be within a single region and that region cannot be the region of origin.
  3. Intra-region flights tend to be shorter and therefore, usually less valuable in terms of premium class product quality.
  4. Utilizing the new United free one-way loophole to maximum benefit requires planning multiple trips in advance.