Hacking Hawaii Revised


Fly half price, stay for FREE

In an earlier post I showed a way that a family of four could vacation in Hawaii for free. The goal of the post was to have an easy way for a family with in-flexible travel dates to take advantage of some great credit card offers without having to struggle to meet minimum spend requirements or to wait for the last moment in the hopes that award availability opens up.

There were a few problems with the earlier post: 1) it was a bit more complicated than most people would be comfortable with; and 2) it required redeeming Chase Ultimate Rewards points for cash which is a bit like throwing away money since there are much better redemption options to be had with those points!

In this post, I’ll aim a little lower (e.g. half price flights instead of free), and I’ll make things much simpler.


In order to make this work, I need to make some reasonable assumptions:

  • This family has good credit ratings
  • Both mom and dad will participate in the solution.
  • Mom and dad are willing to sign up for two credit cards each.

The Solution

As View from the Wing’s Gary Leff reminded me, Bank of America offers an Alaska Airlines credit card which gives card holders 25000 frequent flyer miles and a $99 companion ticket code upon approval of the card (see also, Lucky’s TravelSort article). Combine that credit card offer with Chase’s Marriott Preferred Visa and you will quickly and easily be able to fly a family of four to Hawaii for half price (+$99 for each companion ticket) and stay for free at Marriott resorts.

Step by Step

Mom and dad can follow these four steps:

STEP 1: Sign up for two credit cards each

In one day, both mom and dad should sign up for these cards (note: I do not receive referral fees for any credit card signups):

Alaska Airlines Visa Signature

Upon approval of this card, mom and dad will each receive $99 companion ticket codes and 25,000 Alaska Airlines bonus miles.

Chase Marriott Preferred Visa

After their first purchase with this card, mom and dad will each get 70,000 Marriott Rewards points and a certificate for one free night in any category 1 through 4 Marriott!

STEP 2: Use the Marriott cards

When you receive the Marriott card, make a purchase right away: buy a coffee, fill up your gas tank, buy a $1 Amazon gift card, whatever. It may take a while to get your Marriott points so you want to get this started as soon as possible.

STEP 3: Book your trip via Alaska Airlines

Once you receive your companion certificates, you can go to AlaskaAir.com to purchase tickets. Search for the best deal you can find and then purchase two regular tickets and two companion tickets. In general Alaska Airlines appears to be competitive with most other airlines for flights to Hawaii, and sometimes has fantastic specials. Also, they are often adding new routes to Hawaii so keep an eye on that as well!

STEP 4: Book your hotel

Once both Mom and Dad receive their bonus Marriott points they will have a total of 140,000 points to use for redeeming free hotel nights. Marriott has many great resorts in Hawaii and pretty good availability for rewards, so you should be able to find something very nice. If you need a few more Marriott points, Marriott will let you purchase the difference. Another option is to find points plus cash options. For example, I found that at the Kauai Marriott Resort (see photo below), you could stay for a week for a total of 150,000 points plus $50 per night. Not bad!

Wrap Up

With the simple plan listed above, a family of four can fly to Hawaii for about half price, and can stay in fabulous resorts for free. The great thing is that the credit card deals listed above don’t require meeting minimum spend requirements before qualifying for bonuses. The down side is that you do need to pay regular price for two of the four tickets to Hawaii.

Do you have ideas or suggestions to improve this plan? Please contribute and post your ideas in the comments below!

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