A Beginner’s Guide to Visiting Hawaii on Points
For a long time, Hawaii felt like one of those “someday” trips. Beautiful, yes. Affordable for a family of five? Not so much. But in the summer of 2022 I took my family of 5 to Hawaii for 12 days on one of our most memorable trips to date. And now we’re doing it again!
Read More: Our Grand Hyatt Kauai Review
This summer, we’re doing Hawaii in a way that still feels a little unreal—even to me.
We booked round‑trip flights from Baltimore (BWI) to Maui (OGG) and a stay at the Hyatt Regency Maui almost entirely with points. And the best part? This wasn’t complicated, extreme couponing, or something only travel pros can pull off.
If you’ve ever thought: – “Hawaii is too expensive for families,” or – “Points and miles sound overwhelming,”
This post is for you.
The Big Picture: Hawaii on Points Is Shockingly Simple
This entire trip came down to two core strategies:
- Using the Southwest Companion Pass for flights
- Using Chase points for Hyatt hotel nights
That’s it.
No juggling 10 programs. No elite status required. Just two beginner‑friendly tools that work incredibly well together—especially for families.
Let me show you exactly how it played out for us.
Flights: Southwest to Hawaii Using the Companion Pass
We’re flying Baltimore (BWI) to Maui (OGG) this summer on Southwest.
Here’s how the points broke down:
- 37,000 Southwest points round trip per person
- 3 people booked with points
- 2 companions flying for just the cost of taxes
That means instead of paying cash for five round‑trip flights to Hawaii, we only used points for three—and the other two tickets were essentially free.
Read This: How to Earn the Southwest Companion Pass
Why the Southwest Companion Pass Is a Game Changer
The Companion Pass allows you to designate one person to fly with you for free (plus taxes) on every Southwest flight you book—whether you pay with cash or points.
When both adults have the pass, it’s incredibly powerful for families.
For Hawaii specifically, this matters because: – Southwest flies to multiple Hawaiian islands – There are no fuel surcharges when booking with points – If the price drops, you can reprice and get points back.
For our family, this turned what could have been thousands of dollars in airfare into an actually possible points redemption.
For the cheapest combination of dates, be sure to search using the “low fare calendar.” This way you can see an entire month of prices and choose the lowest prices.
And for an even steeper discount, be sure to check your profile for any discount codes you can apply to your purchase. If you have any of the Southwest credit cards, you should have at least a 10% off coupon code available in your profile.
We were able to bring the price of our award flights down even more by applying one of these coupon codes, bringing our roundtrip cost to just 36,500 points per person round trip plus $11.20. While those same flights would have cost us $937 per person. A total savings of $4,685. Unreal!!
Hotels: Hyatt Regency Maui with Chase Points
Flights are only half the equation—hotels in Hawaii can be just as expensive.
For this trip, we booked the Hyatt Regency Maui for 4 nights and the Hyatt Hana-Maui for 2 nights.
Here’s the breakdown:
- 29,000 Hyatt points per night (available for as low as 25,000 points per night)
- Points transferred from Chase Ultimate Rewards
- A beachfront resort that regularly costs around $700-$800 dollars per night including taxes and resort fees.
Hana-Maui on Points
Then we did the same with our 2 nights stay at the Hana-Maui! This property goes for 25,000-35,000 points per night depending on your travel dates. Since we are traveling during peak times, we’ll be paying 35,000 points per night.
We’ll be using 70,000 Chase points transferred to Hyatt for a 2 nights stay, instead of paying $1,471.46.
Why Hyatt + Chase Is One of the Best Combos Out There
Hyatt is a transfer partner of Chase, which means:
- You can earn flexible Chase points
- You transfer them to Hyatt when you’re ready to book
- You often get outsized value compared to paying cash
At 29,000 points per night, this stay would have been completely out of reach for us paying cash—but with points, it became a realistic (and comfortable) option for a family trip.
Cards I Would Open For a Trip Like This
Note: Offers are constantly changing. Please reach out on Instagram or Facebook for current welcome offers.
Chase Sapphire Preferred® Card
- Visit my Chase Sapphire Preferred® Card guide to learn more!
- $50 hotel credit
- 5X on Chase Travel℠, 3X on select streaming services and online grocery purchases (excluding Walmart, Target and wholesale clubs), 3X points on dining, and 2x on other travel purchases
- $95 annual fee
- All information about the Chase Sapphire Preferred card has been collected independently by Vacation Pointers. The card details on this page have not been reviewed or provided by the card issuer.
Chase Ink Business Unlimited® Credit Card
- No annual fee
- Earn unlimited 1.5x points per dollar on every purchase
- Points can be combined with other Chase cards that earn Ultimate Rewards
- All information about Ink Business Unlimited has been collected independently by vacationpointers.com. The card details on this page have not been reviewed or provided by the card issuer.
Chase Sapphire Reserve for Business℠
- Huge welcome offer, with a big minimum spend.
- $300 annual travel credit, $500 Edit credit, $420 DoorDash value, $200 Google Workspace credit, $120 Lyft Credit
- 8x points on Chase Travel, 5x points on Lyft, 4x points on direct flight and hotel bookings, 3x points on social media & search engine advertising, 1x points on all other purchases
World of Hyatt Credit Card
- 1 free night each year at any Category 1-4 Hyatt hotel or resort
- 9 points total for Hyatt stays – 4 Bonus Points per $1 spent at Hyatt hotels & 5 Base Points per $1 from Hyatt as a World of Hyatt member
- $95 annual fee
- All information about the World of Hyatt Credit Card has been collected independently by Vacation Pointers. The card details on this page have not been reviewed or provided by the card issuer.
“But Isn’t This Complicated?” (Honestly, No)
I want to pause here because this is where most parents get stuck.
They assume: – You need perfect credit – You need to track dozens of programs – You need to spend hours every week managing points
In reality, this trip came from just 2 kinds of points: – Southwest Rapid Rewards for flights – Chase Ultimate Rewards for hotel points.
That’s it.
Once you understand the basics, trips like this become repeatable—not just once‑in‑a‑lifetime wins.
If you’re just starting out, be sure to check out my Start Here resource including my free beginners guide to traveling for nearly free with credit card points!
Why I Love This Strategy for Families
As a parent, my priorities are different now.
I don’t just want cheap travel—I want: – Flights that work with school schedules – Hotels that are comfortable and well‑located – A system that doesn’t add stress to my life
Using points this way has allowed us to: – Visit family more often – Take trips we would’ve skipped otherwise – Say yes to experiences without blowing our budget.
Hawaii just happens to be one of those dreamy aspirational examples, that as it turns out, isn’t that far out of reach!
Final Thoughts: Hawaii Doesn’t Have to Be a “Someday” Trip
If Hawaii feels impossible on your current budget, I want you to know this:
We didn’t earn these points overnight. We didn’t do anything risky. And we didn’t have unlimited time or spending.
We followed a simple, repeatable plan—and this summer, we’re reaping the rewards.
If you’re curious how to build a strategy like this for your family (even if Hawaii isn’t the goal), you’re in the right place.
Because trips like this aren’t reserved for travel experts. They’re available to families who know how to use points on purpose.
If you’re ready to try this, please reach out on Instagram or Facebook! Send me a DM and I would be more than happy to point you in the right direction!!
More on our families free travels!
Family vacations were a near impossibility for us not that long ago. But about 5 years ago we discovered credit card points and miles and now traveling several times a year is the norm for us! If you want to learn more about how our family travels for next to nothing, I would love for you to check out my Quick Start Guide to Traveling with Points and Miles. It is a hobby that has forever changed our lives and given us the opportunity to see the world!
- Grand Hyatt Kauai Review
- Hyatt Regency Puerto Rico Review
- Southwest Companion Pass Trick
- Hyatt Family Plan
- How to Travel for Free with Credit Card Points
