How To Book Southwest Airlines Hawaii Flights (Even When The Website Says You Can’t)

Filed Under: Advice, Southwest
In the interest of full disclosure, OMAAT earns a referral bonus for anyone that’s approved through some of the below links. These are the best publicly available offers (terms apply) that we have found for each product or service. Opinions expressed here are the author's alone, not those of the bank, credit card issuer, airline, hotel chain, or product manufacturer/service provider, and have not been reviewed, approved or otherwise endorsed by any of these entities. Please check out our advertiser policy for further details about our partners, and thanks for your support!

A couple of days ago Southwest Airlines generated a lot of buzz when they started selling flights to Hawaii. The airline published fares of just $49 one-way, including two checked bags, which is an incredibly good deal.

When will Southwest fly to Hawaii?

The airline will be operating the following flights to Hawaii, and also between Hawaiian islands:

  • Nonstop Oakland to Honolulu flights start March 17, 2019
  • Nonstop Oakland to Maui flights start April 7, 2019
  • Nonstop San Jose to Honolulu flights start May 5, 2019
  • Nonstop San Jose to Maui flights start May 26, 2019
  • Inter-island flights from Honolulu to both Kona and Maui start May 12, 2019

Problems booking flights on Southwest to Hawaii

Many people have been confused when they’ve found themselves trying to book flights on Southwest’s website, only to be told that there are no flights available. Specifically, this applies for people booking connecting flights.

For example, say you want to fly from Chicago to Honolulu. You can book a flight there without issue:

But if you try to book a return from Honolulu to Chicago, you’ll be told there are no flights that are scheduled to operate:

No, the flight probably isn’t sold out, and this isn’t some website glitch. There’s a reason this is happening, and it’s sort of dumb, but it’s a thing.

Why Southwest doesn’t sell Hawaii tickets from many cities

One quirk to understand about Southwest Airlines is that they don’t operate redeye flights (where you take off late at night and land the following morning). They’re the only major US carrier to have that policy, and frankly it’s a surprising policy, given that it means their aircraft utilization is lower than with other airlines.

With Southwest’s Hawaii schedule, this means that flights fly from the mainland to Hawaii either in the mornings or afternoons, and then they return from Hawaii to the mainland either in the mornings or afternoons (if they return in the mornings then the planes sit on the ground in Hawaii for a night).

The absolute earliest flight from Hawaii to the mainland on Southwest gets in at 5:15PM. That’s already 8:15PM on the East Coast, and in many cases there aren’t same day connections available to many points throughout Southwest’s network.

However, not only does Southwest not operate redeyes, but they don’t sell overnight connections. So you’d think they’d at least give people this option — say you fly from Honolulu to Oakland in the afternoon, and then from Oakland to Chicago the following morning (and you’d spend a night in a hotel at your expense). But that’s not even something they offer.

The workaround

This isn’t a perfect workaround, but the next best option is to book your ticket as a multi-city itinerary. Since Southwest won’t let you book an overnight layover on a one-way ticket, you’re essentially building your own ticket.

So say you want to fly from Honolulu to Chicago. You could enter the date for which you want the Honolulu to Oakland flight, and then enter the next date for the Oakland to Chicago flight.

Then you can pick the flights you want.

Then it will present you with the cumulative price.

The downside here is that you’re paying the cumulative price of the segments. In other words, Southwest may ordinarily have one price between Chicago and Honolulu, while they’d have a difference price from Honolulu to Oakland and Oakland to Chicago. Sometimes it will be higher, and sometimes it will be lower.

Bottom line

I’ve always been surprised that Southwest Airlines doesn’t operate redeyes, so I’m curious if their new Hawaii service makes them rethink this policy. They’re alienating a lot of non-West Coast flyers by not offering practical connections to a majority of their markets.

At a minimum you’d think they’d sell overnight connections as part of one ticket, since many people probably wouldn’t mind that (heck, they could even start a program where they advertise a “free” stopover at the West Coast city). My hope is that they update their technology, and they just haven’t done it up until now because they haven’t had a need to.

Worst case scenario you can just book your ticket using the multi-city feature, with the flight from Hawaii to Oakland or San Jose on one day, and then the connecting flight the next day. Unfortunately it will be cumulative pricing, but in many cases this could still represent a good deal, especially if redeeming points earned from the Southwest credit card, or if you have the Southwest Companion Pass.

Earn Southwest Rapid Rewards points with:

Has anyone run into this issue trying to book Southwest flights to Hawaii?

The comments on this page have not been provided, reviewed, approved or otherwise endorsed by any advertiser, and it is not an advertiser's responsibility to ensure posts and/or questions are answered.
  1. The RES system was a problem preventing red-eyes, but that is resolved. The pilot contract has rates for red-eyes that Southwest considers unreasonable, but they *can* fly red-eyes per the contract. There is, however, another technical issue. The Ops software that does weight and balance, tracks the fleet, and ties into many other systems like maintenance tracking does not support red-eyes. There has to be a “hard stop” of all scheduled flights at some point each night for the software to cycle to the new day. Right now it is set to something like 4am Eastern. The technology roadmap has that system being replaced, but it has been deferred a couple of times.

  2. I scheduled a flight from ABQ to OGG yesterday. No flight was available direct with connections. I could find the route myself and tried to book it as a mult-city itinerary. Wouldn’t work, got the error on the website. Called in and they had the same error. I had to book two separate one way tickets to make the flight work. No overnight stays, just a stupid computer error.

  3. The real workaround is to buy the $49 Hawaii segments and then book your mainland connections on another airline.

  4. I believe historically WN reservation/scheduling system couldn’t handle the date change. Additionally, they only had 2 schedules. Sunday through Friday and Saturday. With the new system they have reduced unnecessary mid-week frequencies. The new system can also handle seat assignments and other fees. We’ll see how it shakes out.

  5. I did exactly this to book an “overnight connection” in OAK from HOU, and in my experience they priced similar to the HOU-OGG itineraries that were available with the daytime connections.

  6. One potential issue with booking separate legs (say) HNL-OAK and OAK-MDW is the possibility of misconnecting if the first leg is delayed. While I *assume* Southwest would protect the passenger, you would definitely *not* be protected if you were to book the second leg on another airline.

  7. @Mitch – the trouble of course is that outside of WN there’s very little frequency from other carriers at OAK, especially beyond the western US. SJC is marginally better with more transcon flights, esp. AS and AA. And while it will be more doable at LAX and SAN when those start, you’d also have to switch terminals.

  8. Southwest is shooting themselves in the foot for making it so hard for the east coast customers to fly to Hawaii.

  9. This has always been an issue with Southwest, and hasn’t been solved. They don’t allow double connections even if the flight times work, and flights to the Caribbean and Central America leave too early to connect from cities in the West.

    C’est la vie. I can’t fly from OAK to Costa Rica, but I can to Hawaii. And the flights are filling up anyway even without easy connections back east.

  10. @Andy- The WN site does offer multi-city now, you just have to click “advanced search” before it displays.

  11. The vast majority of Hawaii travelers live on the west coast, and that is the initial target market for Southwest. As Hawaii ramps up, I think you’ll see schedule adjustments and maybe even red eyes too.

Leave a Reply

If you'd like to participate in the discussion, please adhere to our commenting guidelines. Your email address will not be published. Required fields are marked *