Planning a Hawaii trip with Chase Ultimate Rewards points is one of the more satisfying redemptions in the points-and-miles world, but only if you know which path to take. The wrong route costs you twice as many points as the right one. Here's how to do it correctly.
What You're Working With Before You Book
The foundation of any Chase Ultimate Rewards hawaii redemption is picking the right card and understanding what it earns. The Chase Sapphire Reserve is currently offering a sign-up bonus of 150,000 Ultimate Rewards points after spending $6,000 in the first three months [^1]. That's enough to cover roundtrip flights and several hotel nights in one shot, if you deploy the points strategically.
The Chase Sapphire Preferred is the lower-fee alternative worth considering if you're earlier in the hobby. Both cards unlock the full suite of Chase transfer partners, which is where Hawaii redemptions actually come to life.
One more thing before you start transferring: Chase points transfer at a 1:1 ratio to most airline and hotel partners [^2]. That means 10,000 Chase points becomes 10,000 partner miles or points, no haircut on the conversion.
The transfer ratio is 1:1, and that single fact is what makes Chase the right currency to start with for Hawaii.
The Southwest Option: Simple, Flexible, Underrated
For many travelers, especially those flying from the West Coast, Southwest Airlines via Southwest Rapid Rewards is the cleanest path to Hawaii. Southwest launched transpacific Hawaii routes and prices them in points based on the cash fare, meaning redemption rates fluctuate.
Chase transfers to Rapid Rewards at 1:1 [^3], so your Ultimate Rewards points move over without any penalty. Key advantages of this route:
- No close-in booking fees - book two weeks out without penalty
- No change fees - cancel and rebook if fares drop in points
- Companion Pass eligibility - points earned through transfers can push you toward the Companion Pass threshold
- Flights available to Maui (OGG), Honolulu (HNL), Kauai (LIH), and Kona (KOA)
The tradeoff: Southwest is a coach-only product. If you want lie-flat business class to Hawaii, you'll need a different partner.
Using Aeroplan for Star Alliance Flights to Hawaii
Air Canada Aeroplan is one of the most flexible Star Alliance programs, and Chase transfers to it at 1:1 [^4]. This opens up United Airlines flights to Hawaii, since United is a Star Alliance member and one of the dominant carriers on transpacific routes.
The routing logic matters here. Aeroplan prices United flights to Hawaii based on distance zones rather than United's own award chart. This can produce meaningfully lower redemption costs than booking through United MileagePlus directly.
Point cost ranges for Hawaii via Aeroplan (one-way, economy) [^5]:
| Route | Approximate Points (Economy) | Approximate Points (Business) |
|---|---|---|
| West Coast to Honolulu | ~17,500 points | ~35,000 points |
| West Coast to Maui | ~17,500 points | ~35,000 points |
| East Coast to Hawaii | ~35,000 points | ~55,000 points |
Those ranges depend on availability and routing, but they illustrate why Aeroplan is worth checking before you default to booking through Chase Travel.
Transfer Chase points to Air Canada Aeroplan, search United metal, and you often find better pricing than United's own program charges for the same seat.
The Hyatt Play: Best Resorts for Points on Each Island
Flights get you there. World of Hyatt gets you into a resort without the $600-per-night sticker shock. Chase transfers to World of Hyatt at 1:1 [^6], and Hyatt's property footprint in Hawaii is strong.
Hyatt uses a category system for redemptions, and several Hawaii properties land in categories that are attainable with a reasonable points balance:
- Maui: The Andaz Maui at Wailea Resort sits in a premium category. Peak rates run high in cash, making points redemptions here particularly strong in value-per-point terms.
- Oahu: The Hyatt Regency Waikiki Beach Resort and Spa is a large property with good availability and a lower category than the Andaz Maui, meaning fewer points per night.
- Kauai: The Grand Hyatt Kauai Resort and Spa is one of the more celebrated Hyatt properties in the system. It sits in a higher category but offers consistent availability.
- Big Island: Options are thinner, but Hyatt does have presence here worth checking before you pay cash.
A practical move: use points for the resort nights that would otherwise cost the most in cash (Maui over a holiday weekend, for example), and pay cash for the nights where you're only sleeping before an early flight.
Earning More Points Before You Book
If your points balance needs topping up before you book, there are a few targeted paths worth knowing. Chase Sapphire and Freedom cardholders can earn up to 10x points when checking out with Paze at select merchants through December 2026 [^7]. Eligible merchants have included United, which means you could stack points while buying incidentals related to the trip itself.
The Bilt Mastercard is also worth mentioning for renters. Some Bilt cardholders have received targeted offers for 10,000 bonus points after $1,000 in spend within 30 days [^8]. Bilt transfers to Hyatt and Aeroplan, the same two partners doing the heavy lifting in this Hawaii itinerary, so it complements a Chase-based strategy rather than competing with it.
How to Stack a Full Hawaii Itinerary With Points
Here's how a realistic itinerary comes together using Chase Ultimate Rewards as the hub currency:
- Earn the base points via the Chase Sapphire Reserve welcome bonus (150,000 points) [^9]
- Transfer to Rapid Rewards for flexible, no-fee roundtrip flights if flying from the West Coast
- Transfer to Aeroplan for United business class or if flying from the East Coast where routing rules matter more
- Transfer to World of Hyatt for resort nights, prioritizing properties where the cash rate exceeds $400/night
- Book Chase Travel for any remaining travel costs where you want the 1.5x redemption value on the Reserve card
The order of operations matters. Transfer to Hyatt first since Hyatt award space can be limited, especially at the Andaz Maui. Then sort flights, since Southwest and United tend to have more award inventory flexibility.
Where This Strategy Has Limits
Chase's Hawaii strategy has real gaps. If you want Hawaiian Airlines specifically, Chase does not transfer to HawaiianMiles [^10]. You'd need a different currency for that. Similarly, if your home airport has poor Southwest or United service, the flight math changes considerably and you may need to look at Alaska Mileage Plan or American AAdvantage instead, neither of which is a Chase transfer partner.
Also: Hyatt's Hawaii properties book up fast, particularly during school holidays. If you're planning a summer trip, start looking at Hyatt availability six to twelve months out before you transfer any points. Transferring points to Hyatt is a one-way transaction with no refunds.
Bottom Line
The most efficient Chase Ultimate Rewards hawaii redemption combines Southwest or Aeroplan for flights with World of Hyatt for resort nights, all using Chase's standard 1:1 transfer ratio to move points cleanly between programs. The Chase Sapphire Reserve's current 150,000-point welcome offer is large enough to anchor a meaningful portion of a full Hawaii trip. Start with Hyatt availability, work backward to flights, and don't transfer a single point until you've confirmed the award space exists.