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 three core strategies:
- Using the Southwest Companion Pass for flights
- Using Chase points for Hyatt hotel nights
- Using Wyndham points for a two-bedroom condo on the Big Island That’s it. Three beginner-friendly tools that work incredibly well together — especially for families.
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.
The Big Island: Club Wyndham Paniolo Greens on Wyndham Points
We’re also spending 4 nights on the Big Island — and this is where the trip gets interesting for anyone who doesn’t have a massive Hyatt points balance.
We booked a two-bedroom condo at Club Wyndham Paniolo Greens for just 15,000 Wyndham points per night.
Is it the Grand Hyatt Kauai? No. Is it the Andaz Maui? Absolutely not. But it’s a spacious two-bedroom condo that comfortably fits our whole family — and it’s perfect for the Big Island portion of our trip where we’re spending most of our time exploring volcanoes, black sand beaches, and waterfalls rather than lounging at a resort pool.
The math here is what makes it so compelling for families. A Hyatt resort that fits our family would cost 35,000–45,000 points per night — per room. So we’d need two rooms, effectively doubling the points cost. Club Wyndham Paniolo Greens gives us all the space we need for a fraction of that.
The best part: Wyndham points transfer from Capital One, Citi and Chase Ultimate Rewards. So if you already have points sitting in either of those programs, you may already have what you need. And because I am a Wyndham credit card holder, I get an additional 10% off award stays bringing our total cost for 4 nights down to just 54,000 points.
This may not be the most glamorous redemption. But it’s a smart one — and I wanted to share it because it might be exactly what makes Hawaii possible for someone with fewer points available right now.
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
Annual fee: $95Welcome offer
Earn 75,000 bonus points after you spend $5,000 on purchases in the first 3 months from account opening.
Key perks
- $50 annual hotel credit
- Complimentary DashPass
- $10 DoorDash promo each month on non-restaurant orders.
- Earn 5x on travel purchased through Chase Travel℠.
- Earn 3x on dining, select streaming services and online groceries.
- Earn 2x on all other travel purchases.
- Earn 1x on all other purchases.
Ink Business Unlimited Credit Card
Annual fee: $0Welcome offer
Earn $750 bonus cash back after you spend $6,000 on purchases in the first 3 months from account opening
Key perks
- Earn $750 bonus cash back (75,000 points) after $6,000 spend in first 3 months
- 1.5x Chase Ultimate Rewards® points on every business purchase
- 5% cash back on Lyft rides through September 2027
- 0% intro APR for 12 months on purchases
- No annual fee
- Free employee cards with spending controls
- Points combine with Chase Sapphire Preferred®, Sapphire Reserve®, and Ink Preferred®
- Doesn't count toward 5/24
- Once per lifetime welcome offer — wait for an elevated offer if possible
Chase Sapphire Reserve
Annual fee: $795Welcome offer
Earn 150,000 bonus points after you spend $6,000 on purchases in the first 3 months from account opening.
Key perks
- $300 annual travel credit — automatically applies to first $300 in travel purchases
- $500 in annual The Edit hotel credits ($250 per booking, 2-night minimum)
- $250 additional travel credit (2026 benefit)
- $300 annual dining credit at Sapphire Exclusive Tables on OpenTable ($150 semi-annually)
- $300 annual StubHub credits ($150 semi-annually, through 12/31/2027)
- $288 in Apple TV and Apple Music subscriptions (through 6/22/2027)
- $120 annual DashPass membership + $300 in DoorDash promos (through 12/31/2027)
- $120 annual Lyft credits + 5x points on Lyft (through 9/30/2027)
- $120 annual Peloton credits + 10x points on Peloton (through 12/31/2027)
- Access to Chase Sapphire Lounges with 2 complimentary guests
- Access to 1,300+ Priority Pass lounges worldwide
- 8x points on all purchases through Chase Travel including The Edit
- 4x points on flights and hotels booked directly
- 3x points on dining worldwide
- Global Entry or TSA PreCheck credit up to $120
- Most comprehensive travel protections in the Chase lineup
- Can now be held simultaneously with Chase Sapphire Preferred®
- Points transfer to 14 airline and hotel partners including World of Hyatt
The World of Hyatt Credit Card
Annual fee: $95Welcome offer
Earn up to 60,000 Bonus Points — 30,000 Bonus Points after spending $3,000 in the first 3 months, plus up to 30,000 more Bonus Points by earning 2 Bonus Points per $1 spent on purchases that normally earn 1 Bonus Point in the first 6 months (on up to $15,000 spent).
Key perks
- Annual free night certificate at any Category 1-4 Hyatt property after card anniversary
- Up to 9x total points per $1 at Hyatt hotels (4 Bonus Points + up to 5 Base Points as a member)
- 2x Bonus Points at restaurants, on airline tickets purchased directly, local transit, and gym memberships
- 1x Bonus Points on all other purchases
- 5 tier qualifying night credits toward elite status every calendar year
- 2 additional tier qualifying night credits for every $5,000 spent
- Extra free night at any Category 1-4 property after $15,000 in calendar year spending
- Automatic World of Hyatt Discoverist status
- Complimentary DashPass membership through 12/31/2027
- No foreign transaction fees
- Points don't expire as long as your account is open
Capital One Venture Rewards Credit Card
Annual fee: $95Welcome offer
Earn 75,000 bonus miles once you spend $4,000 on purchases within the first 3 months from account opening
Key perks
- 2x miles on all purchases — no categories to track
- 5x miles on hotels, vacation rentals, and rental cars booked through Capital One Travel
- Purchase Eraser — use miles to offset any travel purchase including Airbnb and Vrbo
- Up to $120 Global Entry or TSA PreCheck credit
- $50 experience credit at Lifestyle Collection hotels
- No foreign transaction fees
- Transfers to 15+ airline and hotel partners
- Travel accident insurance
- Rental car insurance
- Extended warranty
“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 3 kinds of points: — Southwest Rapid Rewards for flights — Chase Ultimate Rewards transferred to Hyatt for resort nights on Maui — Wyndham Rewards for a two-bedroom condo on the Big Island.
That’s it. And because Wyndham points transfer from Chase, Citi and Capital One, you may not even need to earn a separate currency — you might already have what you need.
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
