Hacking Hawaii Revised


Fly half price, stay for FREE

a beach with people on itIn 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!

a swimming pool with palm trees and a beach

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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Can the two Chase Marriott cards be linked to the same same Marriott Rewards account or do the points need to go into two separate accounts? If so, how do you combine the points down the road? Do you do a transfer or just make two separate bookings?



BC: Great question! The short answer is “yes”, but please read this text from a Marriott Rewards FAQ:

Points may also be transferred to your legal spouse or domestic partner at time of reward redemption provided he or she is also a Marriott Rewards member.
To purchase or transfer points, please contact Marriott Rewards Customer Support at 1-801-468-4000.


The AS BofA also has a $75 non-waived annual fee so it is really a $175 companion ticket. Hawaii tickets are anywhere from $300-500 for coach so the discount is more like 20-33%. Still a great deal but not half off.


Gpapadop & Em: thanks for the clarifications!
Steelsnow: great suggestions. Thanks for contributing some great ideas!


This plan seems more realistic for the average family. I do have a twist to offer that brings the price down more…. Instead of applying for the Alaska card, apply for the two Hawaiian airlines cards currently available with 35k each. They are issued through BofA as well and can be applied for and approved at the same time (from experience – they would need to call to make sure both applications are received, and to let them know they yes they do want both cards). These cards come with reduced mileage awards on HA, so 2 cards x two parents would get them the 4 free flights (at least from airports HA flies from, likely the same as Alaska for most). Well, what if they are from Michigan? I would jump on the current Southwest deal of $59 one way to fly out to their choice of west coast destinations…. And stay for a few days before continuing on to Hawaii! Obviously, they could make this bigger with more cards (I am sticking with one Chase card for each). This would keep them around $300 for their flights, which I am guessing would be less than the Alaska option.

Oh, and for the nights in the west coast city on the way to Hawaii…. I would have them sign up for the Club Carlson promotion starting Thursday for each of them, and then those two nights they are staying in a hotel with the kids while visiting grandparents on Thanksgiving and Christmas would turn into another 100k points sans credit application, which will cover them for at least two nights…


For Alaska award flights I think you need to fly from West Coast Alaska Air hubs. Not sure of the reason but I don’t think you can add a partner flight…can’t recall exactly the restriction on this as I do not use Alaska miles at all.

To Justine: It could easily be one parent with 3 kids, one parent/2 kids/nanny-mohter-father-etc. I just read an article in Details magazine about a family with 1 wife, husband, boyfriend and kiddo…the possiblities are endless:-)


Assumption #4 of yours;
All families have two parents



Justine: Well, I wasn’t assuming that all families have two parents — this was actually targeted toward a specific family — but your point is a good one. Having two adults sign up for credit cards can certainly make things easier.