Best Ways to Travel to Hawaii on Points and Miles

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Hawaii is one of the top bucket list destinations for our Travel Freely members (and, lots of other people out there), but air travel to the Hawaiian islands can be outlandishly expensive.

If you haven’t been to Hawaii, it can often be seen as a pipe dream of sorts—with the high cost of flights and hotels at top of mind. But, thanks to credit card points and miles, it’s actually a much more attainable trip than you might think. Check out some of our Hawaii articles and member success stories to see for yourself.

With the use of points, you can book free air travel to Hawaii a number of different ways. We break down exactly how to use the top rewards programs to book your free trip to Hawaii. Keep reading to see the different types of points and miles that can be used to book flights to Hawaii.

Before we begin, our favorite way to get to Hawaii is through the use of transferable points (like, Chase Ultimate Rewards), as this gives you the most options. Transferable point programs let you transfer your points to any number of airline programs. If you’re not familiar with transferable points programs, please check out our guides:

The 3 Easiest Ways to Get to Hawaii

1. Fly Southwest using Southwest points

Southwest doesn’t have any relevant partners, but their own points are useful especially since they’re fully refundable. Additionally, if you have earned a Southwest Companion Pass, you can fly two people for the price of one.  See: Complete guide to the Southwest Companion Pass.

  • The short story: Southwest points are typically only worth about 1.5 cents per point towards the cost of a flight, but award bookings are totally flexible since they can be changed or canceled with no fee up until shortly before departure.
  • Points required: Varies by route but can be less than other options when cash prices are low.
  • How to find awards: Search for available space at Southwest.com
  • How to book awards: Book online at Southwest.com
  • Key warnings: Keep in mind that if you pay for Early Bird Check-In and then later cancel your flight, you will lose the benefit without a refund. When you change your flight, you keep same confirmation number, so any add-ons stay with your reservation.
  • Transfer from: Chase
Using Southwest Rapid Rewards to fly to Hawaii for Free!

Log into your Southwest Rapid Rewards account and search for your flight route by selecting “points.”

2025 SW airlines flight info

Once you hit, “search” you’ll see a list of all possible award flights and the total number of points you’ll need to book your free flight to Hawaii.

2. The Chase Travel℠ Portal

If you have Chase Points, be sure to check flight prices in the Chase Ultimate Rewards Travel Portal before you transfer your points to an airline. It’s often worth checking to see how many points a flight would cost (especially if you find a reasonable cash price directly with the airlines). Keep in mind that you may not always find the best deal this way—so, it’s always a good idea to compare the points cost before making a decision.

For more information on how to book a flight via the Chase Ultimate Rewards Travel Portal, check out this article.

3. Use Capital One Miles

Capital One Miles are very valuable when it comes to booking travel because they’re super easy to redeem. You can use your card to book a flight directly with your preferred airline and use your miles to reimburse that charge. While you can transfer your points to various transfer programs, the easiest way to use Capital One Miles is through this feature that, when applied, covers any travel expense coded as such on your credit card statement. Put simply, you can reimburse yourself for your travel expenses by redeeming your points as cash back, which makes it very easy to redeem your miles.

Check out these Capital One articles for more information:

Capital One Miles Guide

Is the New Capital One Venture X Worth It?

Best Points and Miles Deals