Reacting to the Latest SW Companion Pass News

I've written about Southwest's Companion Pass on several occasions in the past, since I think it's one of the best travel deals out there. Recently, Southwest had announced that hotel point transfers will no longer count towards qualification for the Companion Pass, a few days later, they made a partial backtrack, giving us until the end of the first quarter of 2017 to make the transfers. Here, I'll discuss what I decided to do with this information, with regards to the points I had stockpiled for a Marriott Hotel + Air Package.

The backstory

Even before Southwest put the dagger into the hearts of many miles/points churners on January 1st, I had been considering using my points transfer to receive Alaska or United miles as part of a Marriott Hotel + Air Package.

I was leaning heavily towards getting the Hotel + Air Package that included 120,000 Southwest miles on January 1st, since that would immediately qualify me for the SW Companion Pass for all of 2017 and 2018, but Southwest understood my plan (and presumably that of many others) to maximize the pass benefit for a full two years. They waited until the very day that would make the most sense to redeem for this package, leaving many scrambling for backup options.

Luckily, I had already written my previous post, where I identified what I feel to be the 2 best alternatives to the Southwest Companion Pass play. As I was forced to consider those alternatives further, I realized that they really weren't that bad. In fact, if you have no into of flying to any of the tropical destinations serviced by Southwest, or you're hoping to fly premium class products, there's really not much reason to have miles and the companion pass with Southwest.

What I'm doing

Despite the fact that I am looking to move into more business-class travel, there's no getting around the value-proposition of essentially doubling the travel-potential of miles with a companion pass. What's more, Southwest flights can be cancelled at any time leading up to the flight, allowing for speculative booking, last-minute adjustments, and general de-stressing of the award-booking process. Finally, I have found that Southwest often has the best redemption values for many routes across the US and the tropics (I just researched a spring break trip to Costa Rica for 2 people for 19k miles, round-trip!). It's an unbeatable combination of perks for me, so I just went all-in!

It took just three minutes by phone to convert my 270,000 Marriott points into a Hotel + Air Package that includes 7 nights at any Marriott Cat 1-5 hotel and 120,000 Southwest miles. The post I referenced earlier looks at the best Cat 5 and 6 redemptions, which is useful because you can always add an extra 30,000 Marriott points later to bump up to a higher award category.

The Bottom Line

If you have a stash of Marriott Hotel points, it's time to cash out for a Marriott travel package. My redemption netted me a SW Companion Pass for all of 2017 and 2018 + 120,000 Southwest miles. Combining the two benefits of this redemption generates $3,200 in free flights. Oh, and lets not forget the 7-night stay in a Marriott, from which I expect to extract about $1,000 of value. The total value of the package works out to about 1.5 cents-per-point, whereas typical Marriott redemptions are worth more like 0.5-0.7cpp!

New Year's Eve and Other Events that Make Hotel Points More Valuable

When valuing hotel points, it's often easy to accept that you won't be getting anywhere near the same redemption numbers as with airline miles. Hilton points are mostly redeemed at 0.4-0.6 cents-per-point and IHG at 0.5-0.7cpp, and so on. Where these values tend to skew favorably is when the hotel's rates are abnormally high because of special events occurring in the area. Today, we'll take a look at this opportunity for point-value maximization by sampling New Year's Eve options and list other potential event opportunities.

New Year's Eve Redemptions by Hotel Group

For our NYE sample, we'll look at a two-night stay from December 30th-January 1st and compare it to a January 20th-22nd stay. While this is by no means a perfect method for comparing the price-difference between a normal stay and a popular event stay, it's a decent starting point. Rather than follow a strict formula for picking properties, I'll try to use examples that best assess each hotel group's sweet spots and shortcomings.

Hilton Hotels

Hilton Hotels in New York City: NYC has the most notable, if not the best NYE celebration in the United States, and less than a month out, many Hilton properties are still available on points, even for our short stay of two nights (sometimes thanks to my Hilton Diamond status). For example, Hilton Time Square quoted me $2200 for our two-night sample stay or 160,000 Hilton Honors points. That may sound like a lot of points, but they're not really that hard to come by and this reflects a redemption value of 1.38cpp instead of the paltry 0.29cpp ($400/140k) offered three weeks later. It is hard to create a higher redemption value than that with Hilton points. There are half-a-dozen Manhattan Hilton properties still available on points.

Hampton Inn & Suites Mexico City: Okay, so I said it would be hard to create a higher cents-per-point valuation than the NYC redemption, but this hotel is always a sweet spot on the Hilton award chart. For 10k HHonors points per night, you can locate yourself right in the center of the action, next to the main square of the largest city in the world. Price for our two sample dates were $300 (1.5cpp) for New Years and for the January dates, making this a great opportunity any time!

In the event that you need Diamond elite status to override minimum stay lengths for busy travel dates, know that it's pretty easy to status-match from another program. I did it through this method, although currently the offer is only for 90 days of status. Hilton seems to offer a few good opportunities per year, so keep your ear to the ground for those moments!

Hyatt Hotels

Cartagena Hyatt Regency: It's no secret I'm coveting a visit to this brand new property, since I wrote about it last month. At $696 or 16k Hyatt points, this hotel is an impressive 4.3cpp redemption for NYE! Even though Colombia is still in its summer high season, moving that stay three weeks into January reduces the price to $418/16k points or 2.6cpp, which is more in-line with typical Hyatt redemptions.

Hyatt Hotels in New Orleans: Both the Hyatt Regency and Hyatt House were going for more than $400 per night, but point redemptions were not available on those dates. It's not clear whether this is because we are so late to the game, or if they blackout those dates. I would guess the latter, since Hyatt Regency houses Big Night New Orleans (which I attended last year!). Hyatt Place was available on points when I searched, but is poorly located for festivities and isn't a great redemption value.

Intercontinental Hotel Group (IHG)

IHG Hotels in San Francisco: It seems IHG hotels are not quite the NYE value that other hotel groups can be, with Holiday Inn Express & Suites Fisherman's Wharf coming in at $610/80k points (0.76cpp) for our NYE stay or $450/80k points (0.56cpp) in January. Both Intercontinental San Francisco and Mark Hopkins Intercontinental were going for just better than 0.5cpp, which I wouldn't even do as a normal redemption, although there's over $300 value to be had in using a free night certificate for one of those properties. In fact, the free night at any IHG property worldwide that every Chase IHG cardholder receives as an anniversary bonus is probably the best way to leverage any higher-end IHG property NYE award redemption.

One thing to note about IHG hotels, particularly the Intercontinental properties, is that I often found New Year's Eve to be sold out of points stays in multiple cities, while the days around it never were. This was not the case in our San Francisco example, but the general trend leads me to believe that these properties just capacity-controlled NYE to where very few people could take advantage of a points stay.

Marriott Hotels & Starwood Preferred Guest (SPG)

Sheraton Times Square Hotel: This hotel, as is the case with a number of other SPG hotels in NYC is going for about 5cpp for our NYE sample dates. Normally, I'd expect 2-3cpp for SPG points, so this is definitely a good opportunity if you don't have a better use for those points (more on that later). Our January price-check saw the same properties, such as this Sheraton, going for about 1/3 the NYE rate, but then again, it is January in the Northeast!

New York Marriott Marquis: I went straight to the best redemption rate I could find, and it certainly is a good one for this NYE booking. At $2,200/90k points for our two-night NYE stay, this hotel is offers us more than 2.4cpp redeeming Marriott rewards points. Since Marriott has recently purchased Starwood and is offering 3:1 exchange for SPG points, you can directly compare the valuation of this Marriott hotel to the Sheraton Times Square. By transferring SPG to Marriott, you'd get $2,200/30k for a valuation of approximately 7.3cpp in SPG points and the Marriott Marquis also gets the better reviews online for what that's worth.

By using Marriott or SPG points, you could achieve 3x their normal value, but there may be an even better redemption. If you've been following along here at Thorpe Travel, you'll remember that I find Marriott Hotel + Air Packages to be just about the best deal in town. If not, go have a look at this post, where you'll learn how to parlay your hotel points into airline miles and still get yourself a nice week-long stay.

Wyndham Hotels

Wyndham Grand Chicago Riverfront: This hotel would make a strong 1.5cpp redemption at NYE prices ($450/30k points for our two nights), but the date is blacked out. It's quite possible that some people managed to snag the booking by planning further ahead, as 2 nights tied into 4th of July are readily available for $620/30k points for a redemption value of nearly 2.1cpp. That's a tremendous redemption value and one could argue that date is a better time to be in Chicago anyway! Just for kicks, I checked our January 20-22 dates and the property was bookable for $250/30k points, or a little bit less than 1cpp, so that 4th of July booking creates double the average value.

Wyndham International Properties: I looked at both all-inclusive properties in Cancun and several other locations without finding availability on NYE, so my guess is that the availability was probably there at some point, but is less than what these properties would make bookable on a run-of-the-mill evening. In general, it seems the key to maxing value on your Wyndham redemptions involves planning ahead.

For those of you not as familiar with Wyndham Rewards, it's a newer program, whereby most any property held by Wyndham is available for a flat rate of 15k points per night. Translation: great values at the higher end properties and terrible values at their lower brands like Days Inn or Super8. You can currently get enough points for three nights by signing up for the Barclay Wyndham Rewards credit card and if you need some inspiration, here's the DOC's list of Wyndham Properties.

Other ideas for high-value hotel award redemption opportunities

  • Major sporting events
  • Location-specific festivals
  • High-season tourism destinations
  • National holidays
  • Conventions and other shared-interest gatherings

The Bottom Line

While we've only just scratched the surface of maximizing our hotel point values by booking during high-occupancy occasions such as New Year's Eve, I think it's quite clear that there are some major opportunities to be found. Even with just 3 weeks until NYE, I was able to find award space at most of the major hotel groups for stays in high-interest NYE destinations and unearthed stays that would triple the value of your points.

Given this data, it seems prudent to consider booking cash on low-occupancy dates if you know you'll need a hotel during a big event. Of course, your valuations will change if you hang onto your points through a program devaluation, so keep that in mind, too.


Travel Together: A Ridiculous Hyatt Points + Cash Redemption in Cartagena

Cartagena City View from Bocagrande

Cartagena City View from Bocagrande

Recently, a group of old friends and I headed to Cabo San Lucas, Mexico for some sun. We had such a good time that there has been talk of taking another trip together. While I would have no problem heading back to Cabo with this awesome group, I thought it might be fun to explore other options for next time. I've also been spending some time researching the Hyatt Gold Passport Rewards Program and How to Always Get 10-15% off Hyatt Hotels. This post will explain how to stack both opportunities for a ridiculously good deal in Cartagena, Colombia!

Why Cartagena for the Next Trip?

Cartagena is an obvious candidate for a future trip for many reasons. The main argument against it is that it's a bit farther away than tropical destinations in Mexico, but in it's favor:

  1. Flights on Avianca (read: nice, new airplanes) from LAX, often for similar prices to other places with tropical weather like Cabo or Cancun in Mexico.
  2. Cartagena feels adventurous compared to more typical US leisure destinations, but enough Americans go that it sufficiently caters to that crowd, too.
  3. Colombia is a discount destination, where most things cost half what they'd cost in the United States. A 15-20 minutes taxi ride costs about $5 and a full meal with drinks at a restaurant can be had for $5-15 per person. Even drinks at trendy nightclubs will only set you back a couple bucks!
  4. Speaking of clubs, Cartagena has a great nightlife scene, whether you want to dance or chill on a rooftop with some beers. There's enough to explore during the day, too, so no need to hang by the pool the whole time (though that sounds good!).
  5. Right now, there is an absolute steal of a hotel award redemption at the Hyatt Regency!

The Hotel: Hyatt Regency Cartagena

This hotel is so new, it isn't even open yet! The Hyatt Regency Cartagena in Barrio Bocagrande is currently taking reservations for December 19th, 2016 and on. From the photos available and information I was able to gather from the website, this is a premium hotel, but somehow it's only a Category 2 redemption for Hyatt Gold Passport members (more on why this is awesome later).

The Hyatt Regency is located just a three minute taxi ride from the main Cartagena action (Centro & Getsemani Neighborhoods) in an area populated by long strands of beach-front, high-rise hotels. Bocagrande is often spoken of as the "Colombian Miami Beach," although the beaches themselves aren't quite as nice.

Getting There: Flights on Avianca and Comparing Destination

First off, I'll make a few assumptions about trip length and appropriate travel dates:

  1. Colombia is a little farther than Caribbean destinations and significantly farther than Pacific Mexican resort towns, so I think 5 days (including the travel days) is the minimum.
  2. Since 5 days is the minimum optimal trip length, I decided to focus on weekends that also fall on US national holidays to reduce time-off work.

What I found is that typical Los Angeles-Cartagena roundtrip prices for dates associated with US three-day weekends are approximately $525-$550. Both sample dates involve the same flights from LAX to Bogota, but I changed the leg from Bogota to Cartagena in the second to show what's possible with an overnight in Bogota. Basically, by continuing to Cartagena the following day, we'd have time to go out and see the nightlife in Bogota instead of arriving in Cartagena at midnight and trying to force a late start to the evening there. This is effectively a two-for-one deal on Colombian cities!

As points of comparison, I checked the Memorial Day Weekend dates for flights to Cabo and Cancun and here's what I found:

The cheapest flight currently available to Cabo on an airline that is not known for crazy add-on fees and screwing up people's travel plans (I'm looking at you, Frontier!) is this Delta flight for $570 roundtrip. Basically, three-day US holiday weekends are out, since Cabo is priced for these...they know when we want to come.

Interjet will fly to Cancun for $460, which is a pretty good fare, considering that's nearly 5 hours of flying. However, at that point, the difference in cost between Cancun and Cartagena is less than $100, so Mexico really isn't that much of a flight bargain compared to Colombia. At that point, getting to visit the more exotic destination is probably worth the extra money.

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Back to the Good Stuff: Insanely Good Hyatt Award Redemption Values

As I mentioned before, I've been studying Hyatt Hotels for ways to travel hack my stays there. You already know from my previous post that you can always get 10-15% off about 500 Hyatt brand hotels throughout North and South America (Hyatt Regency Cartagena is included in this list). In addition, being a Category 2 hotel makes this particular Hyatt a great option for receiving luxury at a low price. I'm just going to leave the Bogota night out of the equation to make things easier to follow (it's easy to find a nice hotel room in Bogota for $50-$60 per night). Here's how I see it on a per-room basis and assuming a 3-night stay:

Option 1: 3 nights X 8,000 Hyatt points per night = 24,000 Hyatt points per room (two people)

Option 2: 3 nights X 4,000 Hyatt points + $55 = 12,000 Hyatt points + $165 per room (two people)

Option 3: 3 nights X 7,000 Hyatt points + $55 = 21,000 Hyatt points + $165 per room (two people)

At this point, you may be wondering where Options 2 and Option 3 came from, so now have a look at these charts below:

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Hyatt allows members to book award stays with a combination of points and cash, which is what was going on in Option 2. This keeps the hotel cost very minimal at $27.50 per person, per day while requiring half as many Hyatt points to execute.

Option 3 is just a variation of the previous option that adds a 3,000-point upgrade to "Club Level." The Club Level rooms are bigger, with better views and on higher floors, but perhaps the most significant benefit is free continental breakfast and "social hour" in the club lounge (read: free booze every afternoon). In Cabo, we really appreciated not having to go out to get breakfast and it was nice to get a good buzz "on the house." The big difference here is that each day we paid about $125 per person for those privileges plus the room in Cabo, whereas here it costs only $27.50 + 3,500 Hyatt points per person.

How good a deal is this? Best available room rates for this hotel start at $160 per night ($200 for club-level) and head north of $350 in high season and popular weekends.

Putting it All Together: Stacking the Hyatt Travel Hacks for Massive Group Savings

Let's just assume that we wanted to get 10 hotel rooms in Cartagena as simply and affordably as possible. Let's see what Option 2 would look like for 20 travelers:

  • 10 rooms X 3 nights = 30 nights
  • 30 nights X 4,000 points + $55 = 120,000 Hyatt points + $1,650

then, utilize the Hyatt gift card trick to reduce the cash part by at least 10%

  • $1,650 - 10% discount = $1,500

If just one of us picked up the Chase Sapphire Reserve credit card, the sign-up bonus plus a little spend would earn enough Chase points to transfer to 120,000 Hyatt points. That man would be an absolute hero and the group could take care of him by buying his food and drinks when we go out! That would leave us with a $1,500 hotel bill, split 20 ways.

Altogether, each person's flight + lodging expenses might look like this:

  • $540 for roundtrip airfare on Avianca
  • $75 for a 3-night stay in a brand-new luxury hotel
  • $60 for a 1-night stay in an excellent Bogota hotel like the B3 Virrey
Hotel B3 Virrey, located  walking distance from Zona T and Parque 93, Two of the hottest nightlife spots in Bogota

Hotel B3 Virrey, located  walking distance from Zona T and Parque 93, Two of the hottest nightlife spots in Bogota

Bogota Party Bus Tours could be fun for a group!

Bogota Party Bus Tours could be fun for a group!

The Bottom Line

For about $675, airfare and lodging for a 5-day trip to Colombia would be covered. Those who made Cabo a 5-day trip spent about $850 ($500+ for lodging, $350+ for airfare, not including a canceled flight fiasco that left several folks stranded another night). Since our hotel in Cabo was all-inclusive, we have to factor in several days of food/drink expenses, but we'd have an extra $175 each to work with and it would be easy to eat and drink lavishly for less than that amount in Colombia.

In short, a trip to Cartagena would be equally affordable to a return to Cabo or another Mexican destination, while providing the opportunity to experience something new together!

Do you want to take a vacation like this with your friends, but need some help planning the trip? Click the Travel Consulting tab at the top of this site to learn how I can be of service!

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 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.