How to Get a $5 Flight to Hawaii in Three Simple Steps

Update March 2014:

The Hawaiian credit cards are now issued by Barclays bank. The steps below will still work. You may find a few outdated links, so here are the current links for the NEW Personal Hawaiian credit card (35K points for $1K spend in 3 months) and the Business Hawaiian credit card (35K points for first purchase). Both cards still have an unwaived annual fee. Good luck!

You want to go to Hawaii?

No problem. That’s EASY.

Start planning what you’ll DO there!


Sound impossible or too good to be true? Think it’s a scam?

It’s not. I did it. Twice.

Save on the ENTIRE COST of a flight and only end up paying taxes – in this case: $5!

Here’s a screenshot from my itinerary to Hawaii:

Not bad, huh? And that picture above was the view from my seat. :-)

What would you think about spending next winter in Hawaii? Perhaps ringing in the New Year in shorts and on the beach?

Well, it’s possiblefor less than the cost of a sandwich, you can be on your way to palm trees, sun, and sand. Guaranteed.


How to Book Your Flight:

1. Apply for the Hawaiian Airlines Visa Credit Card

2. Spend $1000 on the card within 4 months

3. Receive 35,000 points and book your round-trip flight!


I’m not kidding – that is ALL you need to do!

If needed, move all your normal, regular expenses to this credit card until you meet the spending requirements. For most people, food, gas, car, cell phone, and house expenses could easily be $1000 – just in one month!

Once you’re done, you can even cancel the card – after you get the points.


You’ll see above that you get 20K points with your first purchase, and that’s enough points for a one-way ticket! If that’s all you need, you can skip the $1000 spending!

Or, make those purchases and you can get a round-trip ticket out of the deal – though you may not want to leave the island!

This deal works for couples, too: have each person apply for the card and save on both flights!


NOW HANG ON – if you’re intimidated by credit cards – don’t be!

Questions you might be thinking…

Will getting a credit card ruin my credit score?

Not (necessarily) true. Assuming you can use a card responsibly and only for what you need to, you’ll be fine. Just like with any credit, avoid making purchases you can’t afford.

As long as you pay off your balance each month, your credit score won’t be affected much, if at all. Mine has actually gone up.

Will I be limited in my choice for seats when I go to redeem for a flight?

For most programs, there are no blackout dates or restrictions – as long as there are “reward seats” available on a flight, you will be free to book it!

 How much time will this take?

The only “work” you need to do is sign up for the HawaiianMiles program, apply for the credit card, and then use the online system (or call) to book your ticket: that should all take less than 30 minutes!

The other factor is how quickly you spend $1000 (another friendly reminder: normal purchases!).

If you work fast, you could be ready to book your flight in 1-2 months; I’d give yourself 3-6 months just to be safe (in case you have specific dates you need to travel).

Is this illegal?

Not at all. You’re just playing the game better than they (the companies) thought you would. :-)

I was definitely worried when I first did this. I had never acquired miles like this, and had no idea if it would even work! As I got closer to the confirmation screen, I imagined the system wiping out all my miles as maniacal laughter emanated from my screen.

Well, that didn’t happen. In fact, it all worked rather painlessly and smoothly. I couldn’t believe how easy it was to book my flight. With just a few clicks, I was off to Hawaii for $5!


P.S. Know if a credit card is right for you! The LAST thing I want to see is you go into debt or pay those ridiculous finance charges, especially when you’re just trying to save money in the first place! 

P.P.S. With the Hawaiian card, you will need to pay a $79 annual fee, but still: $84 for a flight to Hawaii ain’t bad! If you’d like to avoid that fee, you can either call and ask them to waive it, or I’d recommend getting both AA CitiAdvantage cards (see below) to cover the points needed.


What stops so many people from traveling is the COST. I know that many of us are very careful with our spending these days – cash is tight. So while a Hawaiian vacation sounds nice, it’s usually not in the budget.

Or even if you are determined to go, it can still take a lot of time to save up for a trip.

Not anymore. You can take high prices OUT of the equation and take your trip sooner!


There’s MORE good news…

Hanalei Sunrise, Kaua’i

You can apply these three steps again and again and again – for ANY kind of trip!!

1. Get a credit card

2. Meet the spending requirement

3. Use the points!

I’ve used this 3-step method to:

  • Hop around the Hawaiian islands for $2.50 (the cost of bus fare on Oahu!)
  • Fly from Los Angeles to Boston for $2.50
  • Ride first-class on Amtrak across the country for $0

Friends of mine have saved hundreds of dollars and:

  • Flown round-trip across the United States (even in first class!)
  • Booked a trip from the east coast to California, then a stopover in Japan, and on to Southeast Asia, before coming back
  • Have plans to take their whole family abroad to Greece!

Need even more ideas where to go?

Read about Steve Kamb’s trip around the world for only $418!

Now it’s time for you to do the same!


What to keep in mind as you dive deeper…

 Na Pali Coast, Kaua’i

If you want to keep going with this method, here are some points to remember:

  • Shop around for a credit card – some of the top ones are:
  • How many points does the sign-up bonus offer?
  • Who is offering the points (what airline or rewards program)?
  • How can you redeem those points (will it cover your trip)?
    • Look for “REDEEM” or “USE POINTS” on the site
    • Can you transfer points to another program?
    • You can always book your trip on a partner airline: if you acquire points with American Airlines, you can call up AA and book your trip on Hawaiian, British Airways (or any of their other partners)
  • What is the spending requirement?
  • Do you only need to make a first purchase or is there a minimum amount you need to spend?
  • Is there an annual fee?
    • Most cards waive this for the first year
    • Sometimes it still makes sense to pay the fee – look at what you’ll get for what you’re paying
  • If you get denied for the card, call and ask for a reconsideration.
    • It’s most often just a computer decision when you’re approved or denied, so if you can get a person on the phone, you’re in better shape. They’ll ask you a few questions and will most often be able to give you a response immediately.
    • These companies want to give you the card (so that you’ll just start racking up debt)! Be smart by paying off your entire balance every month. Not only will you avoid those ridiculous finance charges, but you’ll minimize any impact to your credit score.
    • If you’re curious what your credit score is, sign up with CreditKarma for free – they have lots of other great resources for free, too!


I’m committed to helping as many people as possible travel as cheaply as possible!

I know first-hand how amazing travel can be and I don’t want others to feel like it’s out of their reach or years away.

If you’d like support with any of these steps, or if you have points and aren’t sure how to use them, .


A great next step (and free information) is Chris Guillebeau’s series of posts on his Five Million Frequent Flyer Challenge. I’ve referred to this several times!

Here are a few other resources you might enjoy:

  • FlyerTalk: the most popular message board of all the latest travel deals, tips & questions 
  • Frugal Travel Guy: “the world’s expert on flying free”
  • One Mile at a Time: One man’s frequent flyer journey


Next steps for you…

Ala Moana Sunset, Oahu

These will take less than 30 minutes – do them NOW if you can!!

  1. Sign up for the free loyalty program Hawaiian Miles
  2. Apply for the Hawaiian Airlines Visa (enter your HawaiianMiles number on the app)
  3. Optional: sign up with CreditKarma for free to monitor your credit

Anything else?

Practice saying, “Aloha.” :-)

You’re on your way!!!


Once again, I kinda geeked out with the travel hacking. I really love it. If you’d like to learn even more about all this (in addition to the free sites above), I wholeheartedly recommend checking out Chris Guillebeau’s Frequent Flyer Master guide and his ongoing Travel Hacking Cartel. Both links are affiliate (will earn me a commission), and I mention them because I have used both items to help me do this crazy stuff – these items are FULL of content, easy to understand, and will save you money!

What are in these packages?


Frequent Flyer Master: 40-page travel hacking manual, 20-minute audio download, 4-part report on Priceline Booking Strategies, free updates as they’re available, plus the “1 free plane ticket” guarantee! Get the guide.



Travel Hacking Cartel: Chris’ beefed up efforts to “democratize free travel” now includes a membership site with how-to videos, helpful articles, ongoing deals with email/text alert, a hacker community, and the “four free flights per year” guarantee! Join for just $1.


If you need assistance understanding or doing any part of this, or how you can use your existing points, .

Me at Kailua Beach, Oahu

In case you were wondering – ALL photos here are from my three-month stay in Hawaii! :-)


So where will your $5 flight take you? What’s your dream (now – reality!) vacation?

I’d love to hear your answer + any other comments you have below.


Until next time,



**In full disclosure, know that not all deals work for all people – your mileage may vary.

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Former life: actor/office worker/virtual assistant; lived in Los Angeles for 11 years. Since then: sold nearly everything, took a $5 flight to Hawaii, lived there for 3 months, wrote an eGuide about all of it, and still traveling. Currently: digital nomad - looking to improve myself, have fun and serve others.