Free Family Trip to Hawaii Using Points

A Family Trip to Hawaii Using Points

One of the  most aspirational ‘Free Travel’ Hacks out there is the coveted ‘Free Family Trip to Hawaii’.  While the size of your family may dictate just how difficult this endeavor may be, this guide will walk you through the basics of planning a FREE Trip to Hawaii for 3 or more people.

The 1st step is deciding which cities you want to visit.  Personally, we wanted to avoid the more mainstream bustling Honolulu (HNL) and beachfront high rises for the more laid back vibe of Kauai (LIH) and Maui (OGG).  This is important to note because each airline has a HUB that only flies to SOME of the Hawaiian islands.  For Example, Delta flies form ATLanta and Detroit to HNL, and United flies from SEAttle and San FrancisO to OGG and LIH.   You can view the ‘Flight Paths’ of each airline on their respective websites, but here are a few links to the big 3 for a quick example:


United Flight Map – The Most options for a 1-stop flight from CLE to LIH or OGG

American Airlines Flight Map – Only Options were CLE-DFW-  – LIH or OGG

Delta Flight Map – LIH only flies to LAX or SEA, and OGG does those plus SLC.  None of those fly directly to CLE, so we crossed this off our list as well.

So you essentially ‘reverse engineer’ the plan starting FROM your preferred Hawaiian city, back TO Your HOME city.  What if you live in a city with few or no hubs?  Well that sucks…because now this is 50% more complicated.  On top of the inconvenience of HAVING to get a connecting flight, some ‘Points Programs’ make the costs higher or availability less desirable when you have to connect in multiple cities to get to your destination.  Sure you could try to put in ‘CLE to OGG’  in your search, and you might get some flights that don’t cost a fortune…but you’ll probably end up getting something like this:

Those layovers may seem arbitrary, but they’re a direct result of your city only having one direct flight into the ‘To Hawaii’ city…. If the Flight to HNL is at noon, but your flight from CLE to SEA is at 1 PM, you’re gonna have a cumbersome layover that all the free booze in the world wont fix.

So for OUR trip, we 1st figured out which cities served LIH and OGG.  THEN we figured out which of those HUB Cities served CLEveland Airport.   Damn, CLE only has direct Flights out to 7 major cities…  If those cities didn’t fly to LIH or OGG directly, they got crossed off our search list.  (We want to avoid the eternal layovers or more than one stop over).

SEA, SFO, LAX, and DFW all made the cut.  Great!  Now we can look up each individual leg, to see when the flights take place,  and if they’re available with points and for how much.   This is the part of Travel Hacking where experience will help you the most.  Things to note:

For the most part, the same flight will be offered at the same time each day.  So if your Saturday flight is Not in the ‘Saver Award Space’ – Try another Day IF it lines up with when your Cleveland flight lands in the Hub City.




*A year ago when I was first planning this trip, there was a direct route to SEA that is no longer available.  

Hooray – it looks like we can fly from SEA to LIH in a sweet 6 hour flight that leaves at 1:30 PM.  Do any flights leave CLE and arrive in SEA before 12:30?  God I hope so…  [Update: There were none]  Similarly-  The flight back home is available with points too!


Here’s another theoretical option from Delta:


Notice the acceptable layover in MSP, and the somewhat steep price of 40K Delta Points?  We can do better… But now at least we have a jumping off point for comparison.

United has a much better Points Value but the schedules still don’t line up.  But Wait!  Here’s where the actual Travel Hacking comes in.  Thanks to websites like this one you know that Delta is a partner with Korean Air & Air France… and United is a partner of Air Canada and Singapore Airlines among others.

…Who Cares?


We Care.  Because I just saved 67,500 points by booking the EXACT SAME FLIGHT that United was offering me for 172,500 for 105,000 via Singapore Airlines! 

That’s right, Singapore – the airline you didn’t know existed – has a much better ‘Domestic US to Hawaii’ Rate for its PARTNER Airlines, which include UnitedIf you can see United Saver Award Availability in your search, that means you can book that same flight on Singapore airlines for 35,000 round trip, instead of 45,000.  That saves you 10,000 MilePlus Points – x3!  That’s enough to give you another round trip intra-US flight in the future.  (AKA $500 in your pocket.)

TravelHack #2 – Most airlines allow a ‘Free Stop-over’ on Round Trip Flights to Hawaii!


So if you’re traveling with a 2 year old who has never been on a plane before… Maybe a 7 hour layover after a 5+ hour flight isn’t the best idea.  Instead, maybe you use your ‘Free Stopover’ on the way to your Dream Vacation… That can be one or even 29  days – up to you!  We chose a 2 day buffer to give us time to acclimate to the time zone change and to get some pre-LIH Flight rest.

So our CLE – SFO – LIH Flight ended up looking like this:

And return:










Here’s the Itinerary and total fees when all was said and done and we finally found an Itinerary we liked:

Ouch, 172,500 miles!   BUT with Singapore, that # went down to 105,000.  Still a lot of points, but these are flights that would cost $1,200 or so per person, so you’re still getting a great value 3.4 Cents Per Mile to be exact, which is a phenomenal redemption.

But wait a minute, I don’t have a Singapore Airlines card!?

No worries brah.  You got the Chase Ink Unlimited Card a while ago with its 80K Sign up bonus, and your wife did too.  Or maybe you started off small with a Chase Freedom card (25,000 points for signing up).  Those points can be combined with Chases Ultimate Rewards earning cards (Sapphire, Ink) when you step into the big leagues.  Singapore Airlines is a Transfer Partner of the UR Program, AND a few others!   And with the $5K you spent to meet the bonus requirements you’ll have just enough points to fly your family of 3 to Hawaii!

Wow, you just saved me a ton of money –  that’s amazing!  How can I ever repay you?  You can apply for that card via our affiliate link and I’ll get a cool 20K points… and if YOU refer anyone else down the road – they reap that same benefit too!

Awesome.  But what about the Intra-island flights?  I don’t have a Hawaiian Airlines card… I only have that American Airlines card you made me sign up for when the bonus was 60K.  Stupid worthless points.

Hold on there buddy!   American Airlines points shine here – because they can be easily used on the island-hopper flights for 5-8K each ‘hop’.  And since your original ticket is an ‘Open Jaw’ – you can combine the benefits of 2 different points programs into one sky-time adventure!   (Alternatively,  you can use the Chase Sapphire Reserve $300 Travel Credit or the Barclay / Capital One Travel credits to offset the cost of this $95 flight).

Now all I have to do is fine cheap hotels or AirBnB’s on the island… They should be cheap right?  Its only the most beautiful place in the world and a top travel destination of multiple countries.

Uh oh….

I’m not gonna lie to you, hotels in Hawaii are expensive.  Even with points.  BUT if you plan far enough ahead even this can be conquered.  It helps to be in ‘2 Player Mode’ and have a spouse / friend who is able to rack up the Hotel Points side of this equation.  Here are our basic hotel options, excluding BnBs in Maui:

Personally, I like to focus on Hyatt and SPG – both of which are known for their quality properties AND great value.  Plus each one has multiple ways to earn points, so the problem of attaining the higher # required is less problematic.

I’ve decided that we’re going to splurge for this one, and booked the Grand Hyatt Kauai in LIHue near Poipu Beach.  And we took it to the next level by getting a ‘Club Room’ instead of a ‘Standard Room’ because of the extra amenities you get PLUS the delicious Ocean-Side view.

Our fancy room  that comes with free breakfast, snacks and drinks every day came to 33,000  for the upgrade (normally 25K for a Standard Room – which is also very nice) – or 2.7 cents a point.

This is the UR Portal Price for one night at the Hyatt we’re staying at





Remember, anything above a penny is gravy, so we’re doing twice that – awesome!  In our case, we thought not having to plan breakfast and snacks every day was worth it.  When you figure the hotel breakfast is $30 for some reason, snacks are more expensive in Lihue, and the Ocean View Room Upgrade can’t be guaranteed without a Club Level booking– to me it was worth it for the heightened experience.

Note:  SOMETIMES you can get upgraded to a better room (view) for free, especially IF you have status or travel during a rare slow season.

For the Maui Island lodging, we opted for the semi-opulent SPG Westin Villas in the northwest part of the island.  They are somewhat far from the Road to Hana – BUT they come with a FULL KITCHEN and a fold out couch that turns into a bed.  (More on that later).  Like the Hyatt they are also on the beach, and also privy to an incredible water park inside the hotel.  These insane pools are what make the difference between Hotel and Airbnb property worth it IMO.

SPG Villas Beach

Furthermore, SPG and Marriott have a ‘5th Night Free’ policy when paying with cash or points.  So that means our $479 a night hotel was 1/5 cheaper!  Since the Marriott and SPG Hotel merger, their points are now interchangeable at the rate of 3 Marriott points to 1 SPG point and vice versa.  (Gives you a very clear understanding of how companies Value  their own properties, if nothing else!)   Fortunately we had previously signed up for the SPG business cards each to stay under 5-25 .  My wife also got the Personal version when the all  time high bonus was at the rare 35,000 peak last year.  On top of that, Marriott lets you combine points within a household – and via the Transitive Property of Points that means SPG points are combinable too!

So now we’ve got our family of 3 flying 11 hours from CLE to HI, staying in two baller hotels, and paying very little (airline taxes/911 fees) for it.  Sweet!  But… Lets push the envelope a little further.  What good is a dream vacation in Hawaii if you’re forced to watch your adorable but not-quite-good-on-his-own 2 year old son?  Sure you can take turns wading in the ocean or getting massaged on the beach while your spouse does the dirty work… but a tropical date-night (or five) would sure be nice!   And as luck would have it, my sister-in-law and brother who live in SFO would make excellent babysitters.

Turns out – their rate for babysitting is exactly 2 Round Trip Tickets to Hawaii and half the hotels required for this vacation!

Back to the SPG Villas – They have a nice large fold out couch-bed, and since we’re family we don’t mind sharing a room with them.  Plus we can cook food we buy at the market as a family and save money on going out as well.  They paid for their own Hyatt stay (in a less opulent Standard Room) with points themselves…and used the CSR Travel Credit to negate the $180 Intra-Island flights.

FYI: in Hawaii and other Resort’y places, you will often pay a $10-45 RESORT FEE which is a tax they impose on everybody.  But… If you’re not paying with money – you can’t be taxed on it!  Another reason to use points instead of one week’s paycheck per night.

 –   So did my brother’s trip from SFO cost 70,000 Singapore Miles as well?

Nope!  They were only 25,000 British Airways Avios miles each instead.  This sometime lame currency is great for specific ‘Distance Based Flights.’  As they measure the cost of the trip based on how many miles the plane flies to get there… so SFO (West Coast) to OGG can actualy be semi reasonable.  BA Avios is a Transfer partner of both American Express MR and Chase UR, so they were easy to come by as well.

Each of these flights was 25K Avios to get from the Bay Area to HI and back








We have a write up about the experience in Hawaii in general, but hopefully this detailed write up will inspire you to plan a trip like this for yourselves.  These TravelingTricks may seem complicated, but if you follow the guide (above) and ask any questions (below) You can Vacation like a rich person as well!


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View from the Choppa’

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