Four Flight Travel Hacks

“No one in the world gets what they want and that is beautiful.” 

-Wade Watts, Ready Player One

By the 2040s, war, famine, global warming, and the energy crisis had done a number on society.  So much so that most people spent all their free time in the OASIS, a virtual reality universe, that allowed people to shop, play, fight, explore the cosmos, learn, and work, all from the safety of their living room.

And to make things even more interesting, the founder of the OASIS, James Halliday, left an Easter Egg quest, a grand scavenger hunt of sorts.  The winner of the quest would receive his estate, making him or her the richest person alive.  But the quest required skill and knowledge of an arcane subject: the 1980s.  And to make matters worse, an evil corporation was hell-bent on winning the game, to the point of picking off competitors–in the real world.

Sometimes its better to get away, whether its to a virtual reality, or travel.  Travel hacking also requires some skill and knowledge–fortunately not of random 1980s trivia–and can result in some spectacular results in the form of free travel!  Here is a blog post about four travel-hacking tips to earn free flights.

I recently bought a flight for the Fiancé for her bachelorette party.  She is flying to the east coast from California for the long weekend, and with our wedding and honeymoon coming up, we were looking for ways to save money.  Fortunately, with a few travel hacks, we got the flights for free.  As I was buying them, shuttling frequent flyer points around, I realized I actually used three different techniques to buy the flights, so I thought I would share!

There were three ways I used points.

1)     Chase travel redemption.  Redeem points through the Chase travel portal.

2)     Transfer Chase points to a travel partner.

3)     Transfer frequent flyer miles between frequent flyer programs.

4)     Buy a flight and redeem points at the cash back value of 100 points to 1 dollar. (I didn’t actually do this, but it is always in option so I included it here).

First thing we did was pick the flights.  Because of the narrow window of time, we were more concerned with finding a reasonably priced ticket that would give the Fiancé the maximum amount of time to enjoy her weekend. Coming back, the only really good option was a flight with Alaska Airlines. Alaska is not a travel partner with Chase, nor is it an airline we regularly travel, so we had only one real option: Chase Travel Redemption.

I searched for flights on Chase’s travel portal, (now run by Expedia and it’s great!) and just selected the flight we wanted and paid with the Chase points I had accrued. Because of Chase’s 25% bonus, I was basically able to purchase a flight for 25% off.  I got a $158 flight for only 12,664 points.  With most travel cards, it would cost me 15,800 points–you normally redeem points at a rate of 100 points per every dollar the flight costs.

Next up was the Fiancé’s flight back east.  This was a little more interesting because the flight we were looking at was with JetBlue and JetBlue is both an airline we fly often (and so have frequent flyer miles already) and is also a travel partner with Chase.  To figure out the best way to buy the flight we had to do a little math.

First: the flight would have cost $189 to buy up front with dollars.  If purchased with TrueBlue points, we could buy the flight for 12,900 points.

I have plenty of Chase points thanks to a winter of squirreling them away, so we had some flexibility.  First, I could have booked the trip with Chase points.  There are always two ways to purchase travel with Chase points.  You can pay for the flight with your card in dollars and then redeem points you have already accrued in the cash-back fashion.  In this way, 100 points is worth one dollar.  Most of travel cards work this way (i.e. Capital One, Bank of America, and Barclays, to name a few).  To buy the flight with points in this manner, it would have taken 18,900 points.  The other way you can pay is by booking the flight with Chase points through the Chase travel portal. This makes your points 25% more valuable.   It would have taken me 15,120 points to purchase the points through the Chase portal, the way I did for the Alaska flight, with Chase’s 25% bonus redemption.  As you can see, with Chase, it’s almost always better if just purchasing with Chase points to use the Chase portal and purchase with points up front.

The other alternative would be to buy the flight with TrueBlue points.  While the flight cost $189, JetBlue would only charge us 12,900 TrueBlue points if we could find a way to come up with enough TrueBlue points.  Unfortunately, the Fiancé only had about 1,500 TrueBlue points in her account. This leads us to the other travel hacking strategies.

With Chase, you can transfer Chase points to travel partners (a.k.a. your frequent flyer account with that airline) at a one to one ratio.  You can also designate one person, who is also an authorized user and part of your household, and transfer points directly to their frequent flyer account. In this way, I could transfer the balance of points (in this case, 12,000, since you can only transfer in blocks of 1,000) from my Chase points to the Fiancé’s TrueBlue points.

So I did so, with one problem: when I did it, I was looking at the wrong flight, a cheaper one that only required 10,000 points!  This meant we were still 2,000 points short.  I could have just transferred another 2,000 from my Chase points, but then I made an interesting discover.  JetBlue allows you to pool points between friends and family members.  So if you have a travel buddy, like the Fiancé, or friends who are willing to share, you can pool your points to make up this sort of shortfall.  I also have a TrueBlue account with about 8,000 points. After setting up the pool, the Fiancé could access my points and purchase the flight entirely with TrueBlue points.

In sum, we were able to purchase a roundtrip flight from California to the east coast entirely with points.  In total, we spent about 25,000 points to purchase a roundtrip flight across the country.    If I had learned about JetBlue’s pooling program before transferring my Chase points, we could have saved more of my Chase points, but because we are sure to fly JetBlue again soon, I don’t feel too bad about keeping the extra TrueBlue points we have in the pool.

Here again are the four strategies to travel hacking:

1)     Beginner: Buy the flight on your travel card and then redeem the flight with your points, at a 100:1 ratio.  As I mentioned many travel credit cards work this way, and Chase allows you do to this as well, although you shouldn’t normally.  It’s the simplest way to buy flights with credit card points.

2)     Intermediate: If you have Chase or Citi travel cards, you can purchase flights through their respective travel portals, as I have outlined above, and your points are worth 25% more than they would be otherwise.

3)     Advanced: Transfer for travel partners.  This one is again limited to certain cards, (I believe some Amex and Citi cards have similar abilities), you can transfer points to a frequent flyer program with a specific airline, and purchase points directly with that airline using your new frequent flyer miles.

4)     Pooling: You can share points if you have a travel buddy.  JetBlue does this for free.  Other airlines, such as Southwest, will charge you (Southwest charges $10 per 1000 points).  It’s almost always better to use this only if you just need a few thousand more points for a flight, unless like JetBlue, the airline doesn’t charge you at all.




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