Planning a Hawaii trip with Chase Ultimate Rewards points sounds straightforward until you realize there are at least four distinct paths to get there, and they price out very differently. This guide cuts through the noise and focuses on the options that actually deliver value for someone already holding a point balance and ready to book.
Why Chase Ultimate Rewards Works for Hawaii
Chase Ultimate Rewards sits at the center of this strategy because it transfers to several programs that cover Hawaii flights and hotels without routing you through obscure partners or 30-hour itineraries. The two most practical paths are Southwest for inter-island or mainland-to-Hawaii flights, and World of Hyatt for hotel stays. A third path, using Air Canada Aeroplan to book Star Alliance metal, covers situations where Southwest doesn't fly or Hyatt doesn't have a property.
The single smartest move with Chase Ultimate Rewards is matching the right transfer partner to the specific island and travel dates, not defaulting to whatever partner you already know.
All three of these transfers happen at a 1:1 ratio, meaning 1,000 Ultimate Rewards points becomes 1,000 partner points with no conversion penalty. That baseline math is what makes this currency worth optimizing.
The Southwest Option: Best for Budget Flights
Southwest Rapid Rewards is the most accessible flight path for most Chase cardholders. Southwest operates direct routes from multiple mainland U.S. cities to Honolulu (OGG and HNL), Maui (OGG), Kauai (LIH), and Kona (KOA) on the Big Island.
The core advantage here is simplicity. Southwest prices redemptions based on the cash fare, so if cash prices are low, points redemptions follow. A rough benchmark is that Wanna Get Away fares often run 10,000 to 16,000 Rapid Rewards points each way for mainland-to-Hawaii routes when booked well in advance, though peak summer and holiday pricing can push that significantly higher.
Key things to know before you transfer:
- No change or cancellation fees on Southwest means you can book speculatively and adjust later
- Points transferred from Chase cannot be moved back, so only transfer when you have a specific booking in mind
- The Southwest Companion Pass is one of the best deals in domestic travel, but it requires earning 135,000 qualifying points in a calendar year, a threshold you'd pursue separately from a one-time Hawaii trip
Hyatt Resorts: Where the Real Value Lives
For hotels, World of Hyatt is where Chase transfers deliver their biggest premium over cash rates. Hawaii has several strong Hyatt properties spread across the islands.
| Island | Property | Hyatt Category | Approx. Points/Night |
|---|---|---|---|
| Maui | Andaz Maui at Wailea | Category 6 | ~21,000-25,000 pts |
| Oahu | Hyatt Regency Waikiki | Category 4 | ~15,000-17,000 pts |
| Big Island | Hyatt Regency Maui (Lahaina area) | Varies | ~17,000-21,000 pts |
| Maui | Andaz Maui (peak) | Category 7 | up to 30,000 pts |
The Andaz Maui at Wailea is the most-cited sweet spot in this conversation. Cash rates frequently top $800-$1,000 per night during high season. Redeeming at Category 6 or 7 rates puts your cost per point well above the standard 1.5 cents per point benchmark that Chase Sapphire Reserve cardholders get when booking through the Chase portal.
Two practical notes on Hyatt Hawaii bookings:
- Standard award availability at the Andaz Maui can be tight, especially for oceanfront rooms. Book 60 or more days out whenever possible.
- Free night awards from the World of Hyatt Credit Card can stack here, reducing a multi-night stay's point cost meaningfully.
Aeroplan and the Star Alliance Path
If your dates don't match Southwest's schedule or you want to fly a premium cabin on United Airlines or All Nippon Airways (ANA), Air Canada Aeroplan is the Chase transfer partner that unlocks Star Alliance flights to Hawaii.
Chase transfers to Aeroplan at a 1:1 ratio. From there, you can book United flights to Hawaii, including routes from East Coast hubs that Southwest doesn't serve.
Aeroplan prices North America - Hawaii routes on a distance-based chart. A sample pricing range for economy:
- Economy, mainland U.S. to Hawaii (United): roughly 12,500 to 20,000 Aeroplan points one-way depending on distance zone
- Business class, mainland U.S. to Hawaii: roughly 25,000 to 35,000 Aeroplan points one-way
These figures represent a meaningful advantage over booking the same United flights through United MileagePlus directly in many cases, particularly at peak travel times when United's own program uses dynamic pricing. Aeroplan's chart-based pricing holds more predictably.
Turkish Miles and Smiles is a second Star Alliance option reachable from Chase, and it has historically offered low rates on United flights to Hawaii. However, booking fees and customer service complexity make it a better fit for experienced award travelers than for someone making their first Hawaii redemption.
How the Chase Travel Portal Fits In
Not every traveler wants to transfer points. If you hold the Chase Sapphire Reserve, booking directly through the Chase Travel portal gives you 1.5 cents per point toward any flight or hotel - no transfer required, no award availability to hunt.
For Hawaii flights on carriers that aren't Chase transfer partners (think Hawaiian Airlines or Alaska Airlines on certain routes), the portal rate is your only points-based option without going through a different currency.
The portal also recently added a Price Match Guarantee feature for some Sapphire Reserve cardholders.[^1] If you find a lower cash price elsewhere after booking, you may be eligible to have the difference refunded, which could make portal bookings more competitive on hotel rates.
Additionally, The Edit by Chase Travel is a curated hotel collection available through the portal that includes perks like $100 in property credits at participating hotels.[^2] Some Hawaii properties appear in this collection, so it's worth cross-checking before transferring points to Hyatt.
Island-by-Island Point Cost Summary
Here's a quick reference for approximate point costs per island, using the most practical redemption path for each:
- Oahu (Honolulu/Waikiki): Flights via Southwest or portal, ~10,000-16,000 points one-way; Hyatt Regency Waikiki at ~15,000-17,000 points/night
- Maui: Flights via Southwest or Aeroplan/United; Andaz Maui at ~21,000-30,000 points/night depending on room and date
- Kauai: Southwest direct from select cities; limited Hyatt presence means portal or transfer to Marriott for hotels
- Big Island (Kona/Hilo): Southwest serves Kona; Hyatt Regency presence, roughly 17,000-21,000 points/night
Kauai is the island where Chase's hotel transfer options are weakest. If Kauai is your destination, the Chase Travel portal or a Marriott Bonvoy transfer (also 1:1 from Chase) for properties like the Marriott Kauai Beach Club are worth pricing out.
Where the Math Falls Apart
A few situations where this strategy underperforms:
- Last-minute bookings. Award availability at Hyatt Hawaii properties dries up inside 30 days. If you're booking last minute, the portal's flat 1.5 cents per point is your fallback.
- Inter-island flights. Southwest covers some inter-island routes, but if you need specific timing or connectivity, the point costs can exceed what you'd pay in cash for short hops.
- Marriott transfers. Chase transfers to Marriott Bonvoy at 1:1, but Marriott's Hawaii properties carry high category ratings and dynamic pricing that often makes the math worse than a straight Hyatt transfer.
Bottom Line
For most Chase cardholders, the best Hawaii redemption pairs a Southwest Rapid Rewards transfer for flights with a World of Hyatt transfer for a resort stay on Maui or Oahu. If you want premium cabin flights or need Star Alliance routing, Air Canada Aeroplan at 1:1 from Chase is the next-best move. Run the numbers against the Chase Travel portal's 1.5 cents per point rate before you transfer anything - sometimes the portal wins, especially on hotels in Kauai where Hyatt coverage is thin.