Big Wins


In my recent post “Easy Wins,” I described a number of easy tricks that result in free or improved travel.  Many are also “big wins” in that they’ll result in great value for little cost.  Some of the best deals in travel, though, require a bit more effort or understanding.  These also tend to be great for specific situations.  They tend to fit the mold: “IF you want to fly this specific route and IF you can find award space then you’ll get amazing value by doing this…”

Southwest Airlines Companion Pass

If you don’t mind flying economy, and you don’t mind the lack of seat assignments, and you tend to travel in pairs, then this is probably the single most valuable travel trick you’ll ever find.


The deal: Earn 110,000 Southwest Airlines Rapid Rewards points in a single calendar year and you’ll get a companion pass good for an unlimited number of flights for the rest of that year and all of the following year.  Best of all, companion passes can be used on paid or award flights.

How to: There are many ways to earn Southwest points that count towards the companion pass.  Here are some examples:

  • Fly Southwest
  • Earn points through Southwest credit cards
  • Earn points through the Southwest Rapid Rewards Shopping portal
  • Transfer points from hotel programs (NOTE: transferring points from Chase Ultimate Rewards does not count towards the companion pass)

The easiest approach is to wait for Chase to offer 50,000 point signup bonuses for their Southwest Airlines credit cards, then sign up for two of them.  After meeting the usual $2K minimum spend requirements on each card, you’ll need only 6,000 more points to qualify for the companion pass.

Another great option depends upon having a big stash of Marriott points.  Use Marriott’s Hotel + Air Package 3 to get 120,000 Rapid Rewards points and 7 nights at a Marriott hotel for as little as 270,000 Marriott points.  Marriott Travel Packages no longer count towards a Companion Pass.

Best bet is to time all of this activity so that all points are earned early in a calendar year.  That way, you’ll get nearly two full years to use this benefit.

How awesome is it: Even without the companion pass, 110,000 points will result in a lot of free travel.  As I’ve shown before, Southwest points are worth between 1.5 and 1.7 cents each towards travel (assuming you always book “Wanna Get Away” fares).  If we split the difference to 1.6 cents, then 110,000 points will get you approximately $1760 worth of flights.  And, flights booked with points are fully refundable.  With the companion pass, you can double the value you get from those points.  And, now that Southwest flies to some international vacation spots, the value proposition is better than ever.  To play on the words of Southwest commercials… you are now free to move about the country… and beyond.

British Airways Awards

If you have occasion to fly on one of British Airways’ partners, and if award space is available, and if the flight is direct and fairly short, then you can get incredible value from British Airways points AKA “Avios”.

The deal: British Airways has a distance based award chart with incredibly generous pricing at the low end.  One way flights of up to 650 miles cost only 4,500 points.  Considering that most airlines charge a minimum of 12,500 miles per one-way flight and much more if flying out of the country, this can lead to amazing deals. Here is their award chart (borrowed from Travel is Free):


How to: Getting British Airways Avios is easy.  You can signup for the Chase British Airways card 50K offer or transfer points from any of the following transferable points programs: Chase Ultimate Rewards, American Express Membership Rewards, or Starwood Preferred Guest.  Or, in the unlikely case that you have Avios points from Iberia (the airline) or, you can freely transfer points to British Airways.

Once you have a stash of British Airways points, the trick is to find short non-stop (or one-stop) routes on British Airways partners.  Forget about British Airways flights themselves.  British Airways adds huge fuel surcharges which can sometimes make awards cost as much as paid flights!  To see which partner airlines fly out of your local airport, find your airport on Wikipedia and jump to the section titled “Airlines and Destinations”.  Look for flights on OneWorld carriers such as American Airlines, US Airways, LAN, Cathay Pacific, etc.  Also look for flights on BA’s non OneWorld partners: Aer Lingus and Alaska Airlines.

Once you’ve found flights that look interesting, use Great Circle Mapper to determine the distance between airports and compare to the chart above, or use this Wandering Aramean tool to figure out how many Avios are required for the flight.  OneWorld partner flights can be searched for and booked online at, but Aer Lingus and Alaska Airlines award flights must be booked over the phone.

How awesome is it:  Very awesome.  Quoting from this Travel is Free post, some amazing values that are possible include:

  • Boston to Dublin = 12,500 Avios (on Aer Lingus)
  • Miami to Cancun, Grand Cayman, Montego Bay, Turks & Caicos, etc.. = 4,500 Avios
  • West coast to Hawaii = 12,500
  • LA to Tokyo = 25,000 Avios
  • East coast to many places in Europe = 25,000 20,000
    -like Charlotte to London
    -like New York to Dusseldorf
    -like Philadelphia to Paris

I’ve personally used BA points for dirt cheap flights (4500 points each way) between Detroit and New York City and between Detroit and Charlotte, North Carolina.

UPDATE: Within the US, BA awards now start at 7,500 points one-way.

Stopovers and Open Jaws

Many frequent flyer programs allow at least one stopover and/or open-jaw per round-trip award at no extra cost.  Some programs allow both a stopover and an open jaw.  Alaska Airlines allows a stopover on a one-way ticket.  At the minimum, stopovers and open-jaws make it possible to visit multiple cities on one award.  Even better, under some circumstances its possible to use stopovers and open-jaws to book one and a half trips for the price of one.  Let me explain…

Stopovers: A stopover is basically what it sounds like.  It’s a stop en route to your destination. For example, a round trip flight from the US to Rome might entail a stopover either on the outbound flight or on the return in another city (Paris perhaps?).  By booking your trip this way, it is possible to tour both cities  for the same award price as a flight to Rome.

Open-jaws: An open-jaw is a gap in your flight itinerary.  An example would be where you fly into Rome, but return to the US from Paris.  In that case, you get to visit both cities, but transportation between Rome and Paris is handled separately (by train, perhaps).  The open-jaw can be in the middle of your trip (between the destination and the return airports) or at the beginning / end of your trip.  The latter scenario means that you begin the trip from one airport but end the trip at another.  The gap between those airports is the open-jaw.

One and a half trips for the price of one: When a frequent flyer program allows both a stopover and an open jaw, its possible to book one and a half trips for the price of one.  An example would be to fly from the mainland US to Rome, then back to your home airport, then have a stopover there (for many months, if you like), then fly onward to another airport, let’s say to San Diego (hey, why not?).  The stopover in this example would be at your home airport on the return leg of your flight, and the open-jaw would be between your final destination (San Diego) and your home airport.  The result would be a free one way trip tacked onto a simple round trip award.

Two one-ways for the price of one: In the rare case where a frequent flyer program allows a stopover on a one-way award, it should even be possible to book two one-way flights for the price of one!

Frequent Flyer program stopover and open-jaw rules: Travel is Free has a nice infographic about stopovers and open-jaws here.  The infographic shows the following information (among other things):

Round trip awards:

  • United Airlines allows 1 stopover and 2 open-jaws. No longer true.
  • Air Canada allows 2 stopovers or 1 stopover and 1 open-jaw
  • Lufthansa allows 2 stopovers and 2 open-jaws

One way awards:

  • Alaska Airlines allows 1 stopover

How to: Booking awards with stopovers and open-jaws online is usually just a matter of booking a multi-city itinerary and hoping that the online engine prices the result correctly.  Unfortunately, both Delta and United tend to error out as award itineraries become more complicated.  In that case, you’ll have to get on the phone.  Before you do, though, make sure you fully understand the allowed routing rules and make sure that all segments have award availability.  Regarding the rules, here are a couple of key ones to keep in mind:

  • United does not allow a stopover and open-jaw if the award is entirely within the continental United States.  If the award includes Hawaii, though, you should be fine.
  • Delta allows stopovers and open-jaws on continental US (and international) awards, but requires that the open-jaw be shorter than the other flight segments.

For details about booking one and half trips for the price of one (AKA “free one-ways”) please see this MileValue post.

How awesome is it:  The ability to book an extra one-way, for free, as part of a single award makes it possible to stretch your miles much further.  If you plan well in advance, it’s possible to use this technique to get three complete trips for the price of two.  Shoot, just getting to the point of understanding how this works is an awesome accomplishment in itself.  If you’re there, congratulations!  If not, don’t sweat it.  It really is confusing.

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