Does travel hacking work?

Have you heard of “Travel Hacking”?   It sounds pretty nefarious, right?  Something your average person shouldn’t be considering, even if you could figure out how to do it, right?

Its really a lot simpler than that.  Basically traveling by spending points not dollars.  And then figuring out how to maximize the amount of travel you get for your points.  Often by opening up credit cards for the sole purpose of obtaining bonus points.

You probably have points accumulating from all kinds of sources.  Credit cards like Amex or Chase?  Airline frequent flier programs?  Hotel loyalty cards?  If you’re like me, you have points across all kinds of disparate sources, built up over the years.  And like me, you’ve probably looked at redeeming your hard-earned points for flights but gotten completely turned off by the seemingly unobtainable levels of points needed for a one-way trip to somewhere decent.

Furthermore, you’ve been sent letters in the mail enticing you to open a credit card or been followed all over the internet by advertisements touting all kinds of travel rewards programs.

I’ve seen this and always thought the same things: (1) That seems like a lot of hassle to get a free flight and (2) There’s probably a catch, I won’t be able to travel with those points except on a red-eye to Nebraska and (3) It’ll screw up my hard-fought credit card by opening a bunch of credit cards I don’t really need.


But I finally took the plunge and applied for two credit cards to help me pay for a trip I was planning to take.  I did end up getting the trip for free (well, paid some taxes) but it didn’t quite go how I planned.

Oh yes, the trip I got for free was 5 nights at the Mariott Wailea Beach Resource in Maui and two round-trip flights from San Diego to Maui in March 2018 on Alaska Airlines.


But before we begin, here are some important notes:

  • This is a narrative of what I did.  It may not work out in the same way for you.
  • I’ve been fortunate to build up some points balances through work travel and so was able to contribute those points. However, there are resources out there that explain how to build up points effectively from scratch.  You may want to read about “The Chase Gauntlet
  • There is a ton of information out there comparing relative values of cards and points and lots and lots of information about how to maximize points redemptions.   I used many of those sources.  You should too.  I won’t repeat any of that here.
  • Only open a credit card if it is not going to influence your spending.  We’re opening credit cards here solely to gain the benefit of racking up points without changing how much we spend in the grand scheme of things.


Hotel Rewards


This is in three parts:

  1. How I learned to maximize my points accumulation
  2. My experience opening a credit card solely to obtain points
  3. How to spend enough to earn the bonus points


Part 1 – Maximizing points accumulation

Here’s the spoiler if you don’t want to read more:  If you stay at hotels often, try and always stay at the same hotel chain, open a rewards card for any chain you stay at and always book through the hotel’s website (don’t worry, its pretty much always the lowest price).

I travel frequently for work, but booked my own hotels and expensed it up to certain limits.  What I would do is use a price comparison site like to find the cheapest hotel in the area and book through there.  I’d bounce between hotel chains based on their price.

Bad idea.

  1. I found that hotels would not let me associate my rewards membership number with my booking when using discount website
  2. I was diluting my points by accumulating with multiple chains

Its better to try and accumulate all your points on a single chain.  Not only creating a greater balance and therefore moving you towards a decent redemption quicker, but chains also may provide additional benefits the more nights you stay.

Once I got wise, I started visiting the chain booking pages directly and found the prices were pretty much the same as these discount sites.  I ended up landing on Marriott and they had more brands and more discount brands in the areas I stayed (Fairfield Inn, Courtyard etc.) and recently they took over Starwood which has a bunch of brands (Westin etc.).


Part 2 – Opening a credit card

Spoiler:  Its really easy to open a credit card online.  But read the fine print for (a) The minimum spend needed to achieve the points bonus and (b) The annual fee.  You’ll need to be sure you can hit the minimum spend.  And you’ll need to swallow the annual fee as a “tax” of these techniques that lessens the value of the reward you’re getting.

So I’d accumulated quite a few points (110k to be precise) with Marriott rewards and was at a “Silver Elite” level (pretty much the second lowest) from the nights I’d stayed.  Then one day I was browsing their site and found that if you book 5 nights with points, you get the 5th night free.  So 5 nights for the price of 4.  I was also poking around and quickly learned that the redemption value of points was better for the more expensive hotels.

So, I thought to myself, I could use these points to book 5 nights at an expensive hotel.

Some searching around on the Marriott site, I found the Mariott Wailea Beach Resource in Maui . It seemed decent (recent renovation), at a high Category 8 level, at room rates where over $400 in March.  The kicker – 5 nights would cost 160k points (4x40k points).

The problem? I didn’t have that many points, and didn’t think I could ever get that extra 50k points I needed.  That was half as many points again as I’d already accumulated over about a year.

But… then I recalled seeing an offer for a Marriott credit card that gave 80k points as a bonus.  I found the offer on their site and read the terms and conditions back to front.  The key part here was this: In order to get 80,000 bonus points I had to spend $3,000 in the first 3 months.  And it has an $85 annual fee.  On the plus side, it would kick in more nights counting towards the next “Elite” rewards tier, Gold for me.

What followed was a ton of research on rewards cards and whether I should do this.  I didn’t need a new credit card, after all.  And what about that annual fee.  But then it would effectively allow me to book $2,000 of hotel nights in Maui.  I also did some flight research and found some direct flights from San Diego to Maui.  And I obsessed over the annual weather patterns for March and the micro-climates on Maui to determine if March was a good time to go.

Ultimately, I decided to give it a go.  I applied online for the credit card and got approved instantly. This thing is a Chase card.  Unfortunately it didn’t give me the card details instantly, I had to wait a number of days to get it.  I was itching to get going with it.

The good news?  Marriott allowed me to book the hotel, even without enough points.  I need to accumulate the points and trade them in for the rewards certificates something like a week before I go.


Part 3 – Spending Enough to Earn the Bonus Points

Spoiler:  Look for a big purchase you’re trying to make anyway and put it on the card.  Move your regular spending to the card.  And purchase gift certificates for stores you’d be spending money at anyway.

I’ve been on a bit of a frugal kick and wasn’t sure I could spend the $3k in 3 months to earn the bonus points.  But here is what I did:

  1. I had a car repair bill to pay which I was going to pay from savings.  Instead I paid on the credit card and immediately hit $1200.
  2. I hit as many online accounts as possible with recurring or frequent spend (Spotify, Uber/Lyft, Amazon) and switched all of them to the new card.  Now for those things that I spend monthly, they’ll be racking up points on the way to $3k in spend.
  3. I got lost in various Reddit groups about Churning and Manufactured spend.  But came away with one tidbit:  You can purchase store gift-cards on your credit card.  I immediately headed over to Sprouts website and found I can by Sprouts gift cards.  I do my grocery shopping at Sprouts.  In a pinch I’d be able to pre-purchase a month or more’s worth of groceries by buying gift cards, money I’d be spending anyway.  I haven’t had to pull that trigger yet, but I’m watching my balance carefully.


Flight Rewards

Now that I was locked in with a date for the hotel and was on my way to accumulating the points, I needed to figure out how to get there.  Researching flights showed they’d cost $560 roundtrip each on Alaska.  I wanted to get there cheaper.

I had a handful of Alaska points so researched their website but found them to be near worthless.  Furthermore, I found round-trip to Hawaii would cost 40,000 points each way, so a total of 80,000 points for one flight or 160,000 for two.

But… I receive regular emails from Alaska trying to get me to open a credit card.  I searched online and found their offer to get 30,000 points.  Well, that’s not even enough to get 1 person there.  But, more interesting was a free companion pass.  Book 1 ticket, get 1 free, just pay the taxes.  Well, that’d save half the cost.  That seemed good enough to me.


Part 1 – Opening a Credit Card (and getting denied)

Spoiler: You might not get the card or you might get a card but without any of the benefits you wanted, even with stellar credit (over 800).

I applied online for the credit card.  I was worried that I was opening a new credit card so close to the previous one.  My credit score was great (over 800), but still, could it harm it?  This credit card was with Bank of America.

I hit submit and waited for about a minute…

And then got the message that they couldn’t give me a decision immediately and that I’d receive something in the mail.  I started to research for other people encountering the same issue… there wasn’t much info out there.  But I basically assumed I wouldn’t be getting the card.

Travel Hacking bubble burst.  A 50% success rate.  I’d have to figure out how to pay for the flights.

Part 2 – Finding other sources of points.

Spoiler: You can probably use points accumulated elsewhere like other Credit Cards or other airlines to pay for flights.  Go research “<your points provider> partners” like “Alaska Airlines partners” or “Chase rewards partners”.

I happened to be listening to a podcast that mentioned that Avois – the points of British Airways – were transferrable to partner airlines.  Like Alaska.  Hmm… I’d flown to Europe on BA for work so I wondered how many points I had.

Logging into BA, I found 80,000 points.  Enough for a roundtrip to Maui on Alaska, I thought to myself.  However, I couldn’t figure out how to book it.

More research and I found that (a) BA works off a mileage chart.  Using their chart and the Great Circle Mapper I found San Diego to Maui was 2541 miles which seemed to imply only 12,500 points each way and (b) There was some crazy way to use American Airlines website to figure out I could use Avois to book the Alaska flight.  However, I’d have to call BA.

Now believing strongly I could purchase two tickets roundtrip to Maui on Alaska using Avois, I called BA.  I told them the flight dates, confirmed the Alaska Airlines flight numbers I wanted.  They computed the totals and I used 50,000 points to book the flights.  Done.




  • Hotel Resort fee ($30/day) and Taxes: $170.13
  • Flight Taxes: $72
  • Credit Card annual fee: $85
  • Total Spend for trip: $183.13


  • Five nights in Maui = 5x $450 = $2,250
  • Two roundtrip flights = 2x $560 = $1,120
  • Total amount covered by points $3,120


  1. Maximize points accumulation for hotels and airlines by consistently staying at the same chain or flying the same airline as much as possible.
  2. Open a credit card to get points bonuses, but be aware of minimum spending requirements and annual fees.  Don’t assume you’ll get approved.
  3. Look to other sources of points for transfer possibilities (including other airline programs).
  4. Use the tools at the airline or hotel chain to research required points and possible bonuses (like 5 nights for 4, points savers, or special discounts).


So my first foray intro travel hacking… Success!


TODO: Figure out how to rent a car for points.  Not sure if I can pull this off.




Leave a Reply