How I Took My Family of 5 to Hawaii for Free*
Free flights and free hotels - all with regular credit card spending
I recently came back from a week trip to Kauai that should have cost my family of five $10,000.
We paid less than $1,000 — and we could have done it even cheaper.
I’ve written two previous articles on how I get free hotels and free flights using credit card travel hacking that is largely free, or at least very low cost.
In short, we get sign-up bonuses for credit cards, which we treat like debit cards and use for all of our monthly spending, racking up tens of thousands of points and miles each year.
We then use those points and miles to reduce or eliminate our costs on vacations.
If you haven’t read those articles — one of which is focused more on baseline financial literacy in order to achieve the financial stability needed to responsibly engage in credit card travel hacking — those articles are linked below.
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Achievable Luxury Family Vacations
Hawaii is one of those destinations many families assume is financially out of reach.
Flights alone for five people can easily run $700–$1,000 per person, depending on where you live and the time of year you are traveling. Add in hotels, rental cars, food, and activities, and suddenly a family vacation to Hawaii looks more like a luxury purchase than a reasonable family trip.
Here’s roughly what our trip to Kauai would have cost if we paid cash for everything:
Flights for 5: $3,500
Hotel for 7 nights: $6,000
Rental car: $700
Total: $10,200+
Instead, we paid just under $1,000 out of pocket.
For this trip, we used a combination of airline miles and hotel points earned from credit card sign-up bonuses and everyday spending.
Credit Cards
The credit cards that got us the most points that we used for this trip were from Chase.
My husband and I each have the Chase Sapphire Preferred Card, which gave each of us a 100,000 point sign up bonus last year for meeting the minimum spend in three months. This card has a $95 annual fee, and the current sign up bonus is 75,000 points — which is a good offer as the baseline bonus is typically 60,000 points, and the 100,000 point sign up bonus we got last year is only offered once every 3-4 years. The current 75,000 sign up bonus offer is likely the best offer that will be available this year.
Alex also has an Ink Business Preferred Card — which currently is offering a 100,000 point sign up bonus, which is also a good deal as this standard sign up bonus is usually 80,000 or 90,000. This card also has an annual fee of $95.
Both of these cards also have travel insurance, which is a great benefit if things go wrong on your trip.
We also each have an American Airlines credit card that racks up airline miles for our regular monthly spending.
Flights
Our family of five had 10 flights to and from Hawaii, and we got 7 of them free (or nearly free).
First, kids under 2 fly for free as lap infants, so that took care of the baby.
Second, we had enough miles with American Airlines spending on those credit cards to get one-way direct flights from Phoenix to Kauai for 22,500 miles each, plus $5.60 in fees — so 90,000 total miles and $22.40.
Third, we also had enough miles from previous trips to Hawaii on Hawaiian Airlines for a free flight, and we paid cash for the other 3. The reason I booked two one ways with different airlines is because I didn’t want to fly with kids on a red eye back to the mainland, and most Hawaii return flights are scheduled at night these days — so we paid cash for 3/5ths of our return flight.
Otherwise, all of our flights could have been free on American Airlines.
Tips and Tricks for Discounted Flights
Here are my top tips for getting free flights:
We open mileage programs with every airline that we ever fly, and we collect miles for years. Our free return flight was on Hawaiian Airlines — an airline we haven’t flown on in 7 years. But, years ago, I used to get really cheap return flights to Hawaii for my husband and I on Hawaiian Airlines (paying cash on this airline was a better deal than using miles on American), so we racked up some HA miles.
While we used to use cheaper websites like Skyscanner and Kayak to book cheaper flights — we now typically just use those search engines to compare prices and then book directly with airlines since that gives us an extra layer of protection if anything goes wrong. It’s much easier to deal with the airline directly in case of cancellations, delays, and acts of God, versus having to negotiate with a third party.
Hotels
We did a split stay between two hotels for 7 nights on Kauai, and paid for it entirely with credit card points. We used points to book rooms with rates between $750-1000, which we very rarely pay cash for normally.
We usually do a split stay on Kauai with a few nights each on the North Shore — Hanalei or Princeville — and the South Shore — Poipu or Koloa — but this time, our points took us further staying on the South Shore. The South Shore also typically has better (calmer) beaches for little ones. And fortunately, since it was winter, that worked out well for us as it was more cold and rainy than usual on the North Shore during the week we were there.
First, we were able to transfer 120,000 Chase points to our Hyatt account to redeem for 3 nights at the Grand Hyatt Kauai. Hyatt is one of the best value transfer partners with Chase, and it is always (in my experience) more cost effective to transfer the points and book directly with Hyatt. In my opinion, the Grand Hyatt Kauai resort has the best pool on Kauai for kids and families — including a lazy river and a saltwater lagoon with a sandy beach entry. This is also by far the best point redemption opportunity on Kauai. At 40,000 points per night, this is the standard points rate (if we had managed to snag off-peak rates, which are very hard to get, it would have been 35,000 per night, and peak rates are 45,000).
Then, we were able to use the Chase Travel Portal to book 4 nights in a 1-bedroom ocean view suite at the Koloa Landing Resort for 153,000 points — working out to about 38,000 points per night. This resort typically costs over 100,000 points per night for this room directly with Marriott (owner of the Autograph Collection, which this resort is), so this was a steal — even though the value at this resort is not as high as at the Grand Hyatt Kauai. It also had a kitchen, which can help with food costs — especially useful with kids.
If we hadn’t booked Koloa Landing on points, we probably would have booked the 1 Hotel Hanalei Bay with cash. We haven’t stayed there since 2019 when it was a St. Regis, and I truly love the property, but we didn’t have enough points to redeem a room there. I like to balance travel hacking with splurging when I want to and can, so that we’re not beholden just to the budget or the points. However, the pool at the 1 Hotel would not have been nearly as fun for my kids. I personally don’t go to Kauai for the pools — but my kids love a hotel pool. It’s their favorite part of our vacations.
Another North Shore property we’ve liked is the Westin Princeville — it’s a Marriott Vacation Club property, meaning it’s a timeshare. If you attend a presentation (which is 3 hours of your life you’ll never get back), you can get a buy-one-get-one-free helicopter ride. We did this once and it was worth it, but we have no problems attending a timeshare presentation and firmly saying no in order to get something we want for free.
And of course, one of the cheapest options for lodging in Hawaii if you’re paying cash and traveling as a family is to book a condo.
Costco Travel
Utilizing Costco Travel is another great way to save money on trips.
You can save quite a bit of money by putting together a travel package that bundles your airfare, hotels, and rental car all in one — often saving hundreds or even thousands.
But even if you are piecing together elements of your trip — using air miles for flights, and points for hotels — you can use Costco Travel to save on various pieces.
We used Costco to reserve our rental car, which ended up saving us hundreds of dollars compared to renting the car directly. We also lucked out and got upgraded to a Jeep Wrangler at no additional cost (though we got upgraded because they ran out of the car we booked, so we had to pay for it by waiting an hour at the car rental place with 3 kids who had just come off of a 7 hour flight — still, it was worth it, and the delay had nothing to do with booking the car through Costco).
How This Can Work for Your Family
One of the most common questions I get is whether travel hacking can actually work for families.
It absolutely does — but it requires a little planning.
Instead of one person opening a card and earning one bonus, both spouses can participate. That effectively doubles the number of points coming into the household, which goes much further when booking bigger rooms or even suites for families.
Over the course of a year, that can easily generate enough points for multiple flights or hotel stays.
Add everyday spending — groceries, gas, bills, insurance — and those points accumulate even faster.
You can spend a lot of time planning and opening cards each year to rack up the points — or you can do it more casually, opening one or two cards a year per household to offset a more moderate vacation schedule.
The key is that we never carry a balance. Every card is paid off in full every month. The cards are simply tools to capture rewards from money we were already spending.
Over time, those points add up to free or deeply discounted trips.
In our case, 273,000 hotel points and 90,000 air miles saved us approximately $8,500.
Why I Share This
Travel has been one of the best ways for our family to spend time together, expose our children to different cultures and learning experiences, and create memories.
Without points and miles, many of those trips simply wouldn’t happen — or we’d take far fewer of them.
Credit card rewards aren’t magic, and they’re definitely not for everyone.
But for people who already have good financial habits and pay their cards off every month, they can unlock travel opportunities that would otherwise feel out of reach.
A trip for 5 that should have cost close to $10,000 ended up costing less than $1,000.
And if I had chosen to be beholden to points options only, we could have gotten even closer to completely free.
But with a little flexibility, we were able to spend minimal cash to get a week on Kauai that fit our family’s needs — with memories to last a lifetime. And you can, too!
Thats amazing! Sounds like a lot of work, but if you're inclined, like you are, looks like it can reap great rewards. You did a wonderful job of it!
Good to know about Costco Travel. I just joined in order to get eyeglasses at lower prices.... got a pair of progressives with all the coatings for $139. An eye exam was only $89 - $109. Such a deal.!