Travel Hacking Hawaii: How to Go for Cheap

Travel Hacking Hawaii: How to Go for Cheap

Travel Hacking Hawaii: How to Go for Cheap

I’ll call this mild travel hacking Hawaii because of the high fuel surcharge and other taxes that the carrier, Air Canada charges on an Aeroplan reward ticket.  This all started with wanting to take a mini-RTW Aeroplan flight redemption since the rules were changing September 1, 2019.

I spent many evenings staying up until 2am looking at possible scenarios and flight options, with the lofty goal of taking our toddler and 5 month old on a transpacific flight to Asia, and to ultimately see the Maldives from Canada.  You see, since that’s on my lifetime bucket list.

I spent even more time looking at Prince of Travel’s instagram page with his fancy trips and first class flights, lol!

In the end and after much deliberation and discussion with my husband, we decided we couldn’t take our toddler on a 13+ hour flight right now.  It would not be enjoyable (the flight) and it would be too much with a 5 month old on top of our high energy toddler.  Our baby would be a breeze on a 13 hour flight, she is such a chill baby.

I wish that when the airlines start making you pay for a full fare seat at the age of two, that your child would be easy to take on a plane, you know??  To make that added full fare expense worth it somehow?

Anyways, #firstworldproblems.

Here’s what we did with mild travel hacking this time to Hawaii.  When you don’t give a crap about your credit score, travel hacking using credit cards is glorious!!

How to Go to Hawaii for Cheap

We originally got a trip to Hawaii for about $3300 for 3.5 weeks but had to shorten the trip due to health issues with family.  Here’s the breakdown of what we spent:

  • Flights: $520 CAD for three tickets (2 adults, a 2 year old who is full fare now– ugh, and a lap infant)
  • Hotel on the Big Island for 5 Nights: $120 CAD in taxes and fees
  • 1 bedroom condo on Waikiki for 7 nights: $750 USD

Cheap Flights to Hawaii

Cheap-ish flights to Hawaii was achieved via Aeroplan.

From YVR (Vancouver International Airport) to KOA (Kona International Airport) and from HNL (Honolulu International Airport) back to YVR, a similar flight on the search engine aggregator, is $1900- this was a Hacker fare.  However, the usual price is around $2400 CAD.

With Aeroplan, unfortunately we have to take Air Canada back since we prefer a direct flight for our children (which charges more fees than other airlines that you can use for an Aeroplan redemption), this same flight is 45,000 Aeroplan points per ticket (so 135,000 Aeroplan points) and about $520 in taxes and fees.  It would have been about $200 total if we flew United Airlines for the entire trip, but that would mean a stopover on the way back at 4:00am in San Fransisco.  My mom instincts tell me that’s not such a good idea.

For the checked luggage, we will have one free checked luggage since it is an Aeroplan points redemption and we have the TD Aeroplan Visa Infinite credit card.

Savings: $1280 to $1780

Cheap Flight Within Hawaiian Islands

To get from Kona to Honolulu, we can’t rely on teletransport, unfortunately.

We would take a one way flight.  Thankfully Hawaiian Airlines has multiple flights daily from Kona to Honolulu.  The TD Visa First Class Infinite gives you your points fast once you reach the minimum spend from my experience.  No waiting for 3 months before they credit you your points on your account.  So I asked my husband to sign up for the card so we could redeem the money for the one way flights for three tickets between KOA and HNL, which is $378.

Savings: $378

Hotels in Hawaii (for Free)

For the Big Island portion of our trip, we used Marriott Bonvoy points.

First, it started by signing up for the American Express Gold Card and transferring the American Express Membership Rewards (or MR points) to the Marriott Bonvoy account.  I got my husband to sign up for the American Express card too.  I had to create a Marriott Bonvoy account for my husband (of course with his consent) since you can only transfer MR points to accounts in your own name and not to your spouse.  It took under five days to have the transfer completed.

The conversion rate from American Express MR points to Marriott Bonvoy is 1:1.2 per Prince of Travel’s Bonvoy guide.  So, 50,000 American Express Bonvoy points is 60,000 Marriott Bonvoy points.

However, transferring the Bonvoy points from my husband’s account to my Marriott Bonvoy account was very straightforward and easy, and happened right away.  It just took a phone call to transfer the points.  You can only transfer 100,000 points maximum per calendar year though.

The hotel in question was a Category 4, so it cost 25,000 points for each night.  When you redeem for 4 nights with Marriott Bonvoy, you get the fifth night for free.  So we stayed 5 nights for 100,000 Marriott Bonvoy points, and after taxes, it only cost $122.  Of course there’s the daily resort fee of $22 you have to pay, but even that is much cheaper than the regular price of a hotel room and if we paid regular price for a hotel room we would have to pay the daily resort fee anyway.

Here’s what Kayak search says it would cost, or $1191 CAD for five nights.

Travel Hacking Hawaii: How to Go for Cheap

Here’s how much we paid for five nights:

  • 100,000 Marriott Bonvoy points
  • $120 in taxes and fees for the 5 nights.
  • There’s an additional resort fee charged per day, but this would be charged on top if we didn’t use points anyways, so I didn’t count that.

Savings: $1071

Related: PC Travel Review

Cheap Condo in Waikiki

Finding a 1 bedroom condo for under $130 USD a night seems to get more and more difficult as each year passes.  Every time I see rising prices when I search for a condo on Airbnb or VRBO, I think of this lady at a timeshare presentation I went to who called it “HOTEL INFLATION”.  She had a unique accent, so it was more pronounced “OHTELL INFLATION!”.

Anyway, the cheapest I could find was about $1000 USD for 7 nights.  I contacted the owner who offered booking outside from her own website and it was cheaper that route (skips Airbnb fees etc.) and said she stated she provided the same level of service for $250 USD less.  We did this last year too in 2018, and went ‘independent’ and skipped ‘the middle man’.  It was definitely not as great of an experience as before since we didn’t have the protection of Airbnb to complain or provide feedback.  There were cockroaches (baby cockroaches) in the unit and it didn’t feel as clean as it was in 2017.  The company gave us roach traps but there wasn’t much they could do, they said.

Anyway, we’ll see how this experience goes!

Savings: $250 USD

Beating My Travel hackIng Self Up

Of course I know that I could have done a lot better with travel hacking.  We could have gotten a mini-RTW trip and gone to Istanbul, Singapore, and even the Maldives with these same amount of points (or just a little bit more).  But when you have a toddler and an infant you pay a premium to not fly 4 stopovers to get to your destination and aim for the most direct route!

The great thing about a blog is you can review how much you spent previously.  It looks like I got a better deal via Aeroplan points in 2017 when I travel hacked the flight tickets, they were only $75!  However, that was a strict return flight instead of multi-city so it’s not comparing apples to apples.

However, in 2018, when I travel hacked the trip, it was $720 for two adult tickets, after redeeming $280 from a credit card (not Aeroplan because we didn’t have enough points), so I guess we fared a little better than last year!

Still not bad, the free hotel made up for it and the cheap condo in Honolulu helped offset the lacklustre Aeroplan redemption!

In total, our savings for this trip is about $3554 CAD.

Now we can spend this much in Mai Tai’s and Blue Haiwaiians.  Haha 😉

You may also be interested in:

Hopefully this answers the burning question, how to go to Hawaii for cheap! 

Have you been to Hawaii before?

Have you tried travel hacking before?

Wanting to travel hack with your family but don't know how? Here's how we (a family of four including a baby and a toddler) travel hacked Hawaii for cheap flights with kids. A beach trip made cheap, we saved over $3500 on free hotel and cheap international airplane flights. These travel hacks will save you time and money. #traveltips #travelhacks #lifehacks #travel
Wanting to travel hack with your family but don't know how? Here's how we (a family of four including a baby and a toddler) travel hacked Hawaii for cheap flights with kids. A beach trip made cheap, we saved over $3500 on free hotel and cheap international airplane flights to Kona and Honolulu. These travel hacks will save you time and money. #traveltips #travelhacks #lifehacks #travel
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8 thoughts on “Travel Hacking Hawaii: How to Go for Cheap”

  1. Great job on hacking the flights and the hotel for your Hawaii trip. For the condo, I didn’t know you can contact the owner directly about booking a stay instead of going through AirBnB. I guess it depends on the owner and if they want to skip the middle man. Hopefully you will enjoy your stay at the condo.
    I just sign up for my first travel rewards credit card(Capital One Venture One) last week, it’s a starter type travel card with no annual fees so hopefully I’ll get some good use out of it in the next few years. My travel hacking journey is about to begin…haha!!
    Enjoy the rest of your Hawaii trip!!

    • @Kris- I think it depends on the owner, it was a bit vague in the write up and I messaged her to see if it was possible. There’s lots more risk involved going without Airbnb though. Yayyy for your new card….once you travel hack you can’t go back.

  2. Nice job! I love Hawaii. We did some mild travel hacking the last time we visited. Mrs. RB40 went there for work and we tagged along. So we didn’t have to pay for the hotel.
    This year, I did pretty well with travel hacking. We’re going to Thailand and we won’t have to spend much at all. Under $1,000. I’ll write about it soon. Enjoy HI. I’d love to live there for a year someday.

  3. Totally understand the travel with little ones sentiment. Prior to have a kid we would take whatever flight was the cheapest no matter how m at stopovers. Now we are all about the direct flight ha ha.

    Have never thought to calculate how much we save by travel hacking. Will totally try to do this the next time we book a trip.

    • @Maria- Direct is the way to go. Direct bus, direct transportation, away from public, in the back of the plane. Our kid did actually really well on the night time flight (I was worried he would keep everyone up).


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