Hawaii, anyone? 🌺
If a trip to Hawaii feels like a “someday” dream because of flight prices and resort costs, let me introduce you to one of my favorite points-and-miles combinations that can turn that dream into a nearly free reality.
We’re talking:
✔️ Southwest flights (with the Companion Pass)
✔️ Hyatt hotels on points
✔️ Chase points doing the heavy lifting
Let’s break it down simply.
✈️ Getting to Hawaii with Southwest Airlines (and the Companion Pass)
Southwest might not be the first airline people think of for Hawaii, but it should be—especially for families or couples. The Companion Pass works so well here, and combined round-trip for two to Hawaii at $22.40 total? Not too shabby!
Why Southwest works so well for Hawaii:
Flies to Honolulu (HNL), Maui (OGG), Kona (KOA), and Lihue (LIH)
No change or cancellation fees
Free checked bag for cardholders
🧡 The Southwest Companion Pass
The Companion Pass allows you to bring one person with you on every Southwest flight for just the taxes ($5.60 one-way), whether you pay with cash or points. That means you’d be able to book your flight with points, and your companion flies for just the taxes to Hawaii for the duration of that pass! For families, this can easily save tens of thousands of points per trip.
🏨 Staying in Hawaii with Hyatt points
Hyatt is hands-down one of the best hotel programs for Hawaii on points. They are lower award prices compared to other hotel chains, while IHG only has one property. Hyatt has excellent resort properties and no resort fees on award stays!
Popular Hyatt options in Hawaii include:
Hyatt Regency Maui
Andaz Maui
Hyatt Regency Waikiki
Grand Hyatt Kauai
Depending on the property, you could be looking at 30,000-50,000 points per night for hotels that often cost $500–$900+ per night in cash. That’s where strategy matters.
🔁 The secret sauce: Chase points → Hyatt
Hyatt doesn’t have many credit cards of its own, although they are supposedly adding an additional card later this year. But that’s okay…
Why? Because Chase points transfer directly to Hyatt at a 1:1 ratio, and Chase has some of the most beginner-friendly cards out there. Often times, you can get 2 cents per point when transferring Chase points to Hyatt, depending on the property.
Best cards to earn transferable Chase points:
Other Ink Business cards (Ink Unlimited or Ink Cash) These are great even for small or side businesses)
These points can be:
➡️ Transferred to Hyatt for hotels
➡️ Used for Southwest flights
➡️ Or combined together for one seamless Hawaii trip
✨ What this could look like in real life
Let’s say:
You earn a Southwest Companion Pass
You use Southwest points for flights to Maui
Your companion flies for almost free
You transfer Chase points to Hyatt for 5–7 nights
You could realistically:
Fly two people to Hawaii for under $25 in taxes
Stay at a beachfront resort on points
Avoid resort fees
And save thousands of dollars
All by using points strategically!
✨ Final Tips to Maximize Your Hawaii Points Trip
✔ Be flexible with dates — award space opens and closes frequently
✔ Mix & match flights and hotels if you need to stretch points
✔ Book early — Hawaii award seats go quickly, especially in peak seasons
✔ Keep both airline and transferable points — they give you options
🌴 Final thoughts
Hawaii doesn’t have to be a once-in-a-lifetime trip!
With Southwest + the Companion Pass, Hyatt’s strong award chart, and Chase points as your foundation, it can become a repeatable vacation—one you take again and again without paying full price.
And if this feels overwhelming? That’s exactly why I do what I do. 💛
You don’t need all the cards. You just need the right ones, in the right order, for your travel goals.
Hawaii, anyone? 😉
