Unlock A Free Hawaii Flight This Fall

One of the easiest airfare hacks we’ve ever used just came back—and it still feels like a bit of a cheat. Book any Southwest flight by June 27, fly it by August 31, and they’ll hand you two months of Companion Pass. While two months isn’t long, it does mean that someone flies with you for free (plus a few bucks in taxes) on every Southwest route—including Hawaii—between September 8 and November 15.

We tried this earlier in the year and almost didn’t believe it would work. But it did. One of us flew from Honolulu to Kona round-trip for $80, and the second ticket was free, not “points” free, but actually free.

Southwest brought this deal back without much fanfare. But if you’re heading to the islands—or thinking about a fall getaway—you should probably grab this before it disappears again.

How the offer works.

Register first by logging into your Rapid Rewards account. Then, book a qualifying round-trip or two one-way Southwest flights by June 27 using cash, Rapid Rewards points, or Cash+Points. Fly that trip by August 31. Once you do, your account gets upgraded with Companion Pass status, valid from September 8 to November 15, 2025.

During that time, your designated companion flies free on any Southwest flight as often as you want. They’ll pay only taxes and fees, usually around $11 for Hawaii routes—no blackout dates. No hoops.

And it doesn’t matter where your qualifying flight goes. You could fly from San Diego to Vegas or wherever you’d like and unlock two months of free flights for your travel buddy.

Another benefit is that the name of your designated companion can be changed up to three times during the Companion Pass period.

Why fall in Hawaii is the real sweet spot.

This deal lines up with one of Hawaii’s best travel windows. Flights are cheaper after Labor Day and before Thanksgiving, beaches are emptier, and hotel prices return to earth. It’s still warm, swimmable, and much easier to enjoy.

Southwest flies nonstop to all four major airports—Honolulu, Maui, Kauai, and Kona—with connections from cities like Phoenix and Vegas. We’ve seen round-trip fares from California dip below $260. Add Companion Pass, and that’s two tickets for nearly the price of one.

It also works for interisland flights. If you’ve been meaning to visit other islands, this is a low-cost option.

Don’t miss the fine print—or the deadline.

You must register before booking—there are no exceptions. If you already have a Southwest flight lined up, you can cancel and rebook it after registering, as long as the price hasn’t gone up.

Your qualifying flight doesn’t need to go anywhere near Hawaii. It just needs to happen by August 31. A quick hop between California cities works fine, even if it costs less than $50.

The pass kicks in once you’ve flown a round-trip or two one-way flights. Then you can add your companion to any trip through November 15—even on flights you’ve already booked.

No elite status. No credit card games. All you need is a Rapid Rewards account, which is free and takes about a minute to set up.

We used the Companion Pass, and it worked.

Beat of Hawaii covered this same offer earlier in the year. We tried it ourselves. It delivered.

To trigger the pass, we booked a round-trip interisland Southwest flight. That unlocked two months of free companion travel. One of those flights was a last-minute interisland hop. Another reader told us they used their pass on a California to Maui trip that would’ve cost nearly $500 for two. They paid for one ticket and taxes on the second.

The best part? It was simple. The free ticket was booked like any normal fare. The companion flew in the same class, boarded with the same group, and wasn’t treated like a tag-along.

We don’t say this often, but this one does what it says.

Why Southwest still matters in Hawaii.

Even after pulling back some routes, Southwest isn’t going anywhere. It’s still one of the best ways to fly to Hawaii from the mainland and interisland.

Interisland, Southwest is now the only real alternative to Hawaiian. That keeps both carriers in check. That’s why we see deals like this Companion Pass offer: not just noise but actual value.

With fall fares already softening and routes in flux again, this is one of those windows when it pays to move early—before prices swing the other way.

What to do now.

Register for the deal before you book. Then book any Southwest flight by June 27 and fly it by August 31. Once that flight’s complete, you’ll get a Companion Pass from September 8 to November 15.

You can use it as many times as you want during that window. Your companion pays taxes. You can swap the companion three times if plans change. And it only works if you’re flying too.

The clock’s ticking. If you’re thinking about it, book it.