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One of your most requested destinations has been Hawaii, so I thought I’d go over the many ways to book a Hawaii vacation for almost free! Based on my research, the cash cost of roundtrip flights and 4 nights in Hawaii could be over $4,500. However, if you leverage reward points, this trip can cost as little as $22!
Have I gotten your attention yet? Let’s break it down…
Flights to Hawaii with Points
There are several ways to book flights to Hawaii using points, depending on your preferred airline and rewards program. Here are some options we explored:
- Southwest Airlines: You might use ~30,000 Rapid Rewards® points + Companion Pass to cover 2 round-trip tickets. Taxes and fees would typically be $11.20 each.
- Delta SkyMiles: Flights from the West Coast can be found as low as 25,000–45,000 SkyMiles roundtrip.
- United MileagePlus®: Award availability for ~45,000 miles roundtrip.
- Singapore KrisFlyer: Redeem ~39,000 KrisFlyer miles on United-operated flights.
- British Airways Avios: Use Avios to fly American Airlines — as low as 26,000–40,000 roundtrip, distance-based.
- Turkish Airlines Miles&Smiles: Only 15,000 miles roundtrip in economy — yes, really! But requires more effort.
Tip: If you’re not sure which credit card points transfer to which hotel and airline partners, download our free Transfer Partner Cheat Sheet for a quick reference.
Hotel in Hawaii with Points
Let’s say you wanted to stay at the Hyatt Regency Maui Resort and Spa, where four nights could cost around $3,564. Here’s how you might use points instead:
As of 2025, this property is classified as a Category 6, which means:
- Off-Peak: 21,000 points/night
- Standard: 25,000 points/night
- Peak: 29,000 points/night
Booking at the standard rate of 25,000 points per night would total 100,000 World of Hyatt® points for a 4-night stay.
Those points can be transferred from a Chase Sapphire Preferred® Card, which offers 1:1 transfers to Hyatt. One welcome offer can cover the entire stay!
Other hotel options for Hawaii travel:
- Marriott Bonvoy and Hilton Honors: Good availability, but dynamic pricing means point requirements are often much higher
- Airbnb / VRBO / Vacasa: Use Capital One® miles or Citi® points as statement credits
Side-by-Side Comparison: Points vs. Cash
| Expense | With Points | Cash Price |
|---|---|---|
| 2 Flights to Hawaii | 30,000 Southwest® points + Companion Pass | $1,059 |
| 4 Nights at Hyatt | 100,000 World of Hyatt® points | $3,564 |
| Total | 130,000 points + $22.40 | $4,623 |
Plan Your Own Dream Trip
While this wasn’t a trip we personally booked, these are the exact strategies we would use! A couple of well-timed credit card welcome offers and a thoughtful earning strategy can turn this dream trip into your reality.
Want to take a similar trip? Here’s how to get started:
- Choose your destination
- Look at what airlines and hotel brands serve it
- Reverse-engineer the points you need
- Pick the right credit cards to help you earn those points
Want Help Planning Your First Points Trip?
I offer free personalized credit card consultations to help you:
- Create a smart points strategy tailored to your goals
- Choose the right cards in the right order
- Maximize welcome offers and transfer partners
- Start planning real trips with real rewards
Request Your Free Consult
Editorial Disclosure: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline, or hotel chain. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.
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