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Planning to Connect on Southwest to Hawaii? Here's What You Need to Know

March 04, 2019
10 min read
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First, the good news. Southwest is selling tickets to Hawaii! Now, the bad news. It appears that it's not such a scorching deal for anyone who needs to make a connection from a city east of the Pacific Time Zone.

While we're seeing one-way fares as low as $49 (or 1,950 points) from many of Southwest's West Coast gateways, availability and pricing seem volatile at best for those requiring a connection or two. Southwest plans to eventually fly from four California cities: Oakland (OAK), San Diego (SAN), San Jose (SJC) and Sacramento (SMF) to Honolulu International Airport (HNL), Lihue Airport (LIH), Kona International Airport (KOA) and Kahului Airport (OGG). But it isn’t launching all of those routes at once. Intra-island flights within Hawaii will also come later.

Southwest Airlines crew celebrate their inaugural flight to Hawaii at the Honolulu International Airport, Tuesday, Feb. 5, 2019, in Honolulu. (Photo by Marco Garcia / The Points Guy)

We've pushed Southwest's booking portal to its limits by testing out fare possibilities from a variety of cities to give you an idea of what to expect if you're hoping to Feel The Aloha LUV while originating from states like Missouri, Colorado, Georgia and New York — basically, anywhere not named California.

East Coast

In testing Southwest's booking engine with East Coast cities, we're seeing a mixed bag of results in terms of what's bookable and when. To boot, this seems to be rapidly changing.

Within an hour, availability and pricing on the airline's Low Fare Calendar was markedly altered when looking at trips between Raleigh-Durham (RDU) and its three destinations in Hawaii.

Another oddity is New York City. While flights to Hawaii originating from LaGuardia (LGA) show no availability from now through the end of the booking window (currently pegged to Oct. 1, 2019), solid availability was found from Newark (EWR).

Perhaps unsurprisingly, Southwest is showing the most availability from its hubs, including Baltimore/Washington International Thurgood Marshall Airport (BWI).

Cities such as Atlanta (ATL) and Orlando (MCO) had plenty of available options, while the likes of Philadelphia (PHL), Boston (BOS) and Portland (PWM) showed practically no dates available for booking.

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We've also found that even in months with ample options from East Coast cities, such as a full calendar between Raleigh-Durham and Maui in August, there's no availability for a return. While you can purchase tickets nearly every day in August from North Carolina's capital to Kahului (OGG), you cannot yet book a return on any day.

For now, it appears that East Coast dwellers are better off hanging tight with Southwest's entrance into the 808. Fares aren't spectacular, and we can't say for sure that all connection options are loaded just yet.

Midwest and Central US

In the Midwest and central US, research suggests that bookable flights to Hawaii primarily show up for cities that currently fly direct between Oakland (OAK). For instance, flights operate nonstop between Austin (AUS) and Oakland (OAK), so Austin to Maui by way of an Oakland stop is available on a number of dates. However, those flights aren’t available every single day.

Once again looking at Austin as an example, the Southwest weekly flight schedule shows that AUS-OGG flights are only available Wednesday through Sunday for the week of April 7-13, and Sunday through Friday the following week of April 14-20.

Given that you can only fly Southwest between Minneapolis-St. Paul (MSP) and Honolulu (HNL) a single day in August, we're left to surmise that the airline is still populating its booking engine. We expect these results to change quickly.

Departing from Indianapolis is totally doable in July, but beware of the Hotel California vibe waiting on the other end.

Southwest has yet to publish any one-way return flights from Honolulu back to the Hoosier State (and most other states, for that matter). This is most likely due to the lack of scheduled redeyes, as Southwest doesn't want to sell itineraries that force you to sleep in an airport or get an overnight hotel before continuing on. Then again, there are worse places to be trapped than Oahu.

There are entire states that seem to be all but ignored. Southwest has yet to load a single route between Cleveland (CLE) and Maui/Honolulu.

Two hours down I-71, Columbus (CMH) is devoid of options until September.

Given Southwest's presence at Chicago, it's not a surprise to see ample flights out of Midway Airport (MDW).

In fact, Chicago is one of the few cities where Southwest has published fares for a return flight back to the mainland. (Though, the prices are far from attractive when looking at a points redemption.)

Western US

Generally speaking, the closer you get to California, the more likely you are to see wide availability of Southwest flights to Hawaii.

Available dates are far easier to find when originating in the western US through cities such as Boise (BOI), Phoenix (PHX), Denver (DEN) and Portland (PDX).

Phoenix (PHX) has far more daily flights between Oakland, which is accordingly reflected in the weekly schedule for an example week in mid-April. You’ll see that, while there are a number of flights that depart Phoenix at various times throughout the day, all of them funnel into the two daily flights between Oakland and Maui for those dates: Flight 3143 which arrives in OGG at 11:05am, or Flight 1466, which arrives in OGG at 8:00pm.

For example, you can fly between Portland (PDX) and Honolulu (HNL) every single day in August.

You'll even have your pick of connection options, including a route through Oakland as well as San Jose.

Erratic behavior is still found, even from western cities. Departing from Albuquerque (ABQ), you're able to book a seat to Honolulu practically every single day in September.

In July, however, you're out of luck unless you're game to pay sky-high rates to fly in on a Sunday.


Southwest now serves 14 international destinations, including locales in Mexico, Cuba, Belize and Costa Rica. We did our best to irk the airline's booking portal by searching for fares between each of those outposts and Hawaii.

With a sole exception — Los Cabos (SJD) — Southwest has yet to enable ticket sales between its non-US cities and America's 50th state. We suspect that will change in due time, but these routes will likely be enabled after US connections are ironed out.

Bottom Line

Maui's Haleakala National Park is calling (Photo by Darren Murph / The Points Guy)

Considering that Southwest just began selling seats to The Aloha State, we aren't surprised to see wonkiness when it comes to routes that require connections. Clearly, the airline's California passenger base is in focus at launch, and we know there are plenty of flyers in San Diego as well as the Bay Area who will be quick to fill its first flights up.

Given the spotty availability and illogical pricing on many connecting routes, we'd advise patience. There appears to be no rhyme nor reason to what cities and dates are bookable, and frankly, pricing is higher than what we're seeing on legacy US carriers. Our advice is to either snag a cheap Southwest ticket from its West Coast cities and book a positioning flight elsewhere using points and miles, or be quick on the trigger when legacy carriers begin to sell attack fares as we've seen with American Airlines.

To get prepared for when schedules are fully loaded and fares settle down, consider boosting your Southwest Rapid Rewards point balance with one of the credit cards below.

  • Southwest Rapid Rewards® Priority Credit Card ($149 annual fee) — This card is offering 40,000 bonus points after you spend $1,000 in purchases in the first 3 months. You'll also get 7,500 bonus points after your cardmember anniversary, a $75 Southwest travel credit each year, 4 upgraded boardings per year (when available), 20% back on inflight drinks and Wi-Fi and 2 points per $1 spent on Southwest purchases and Rapid Rewards hotel and car rental partner purchases. You'll earn 1 point per $1 spent on all other purchases, and there are no foreign transaction fees to sweat.
  • Southwest Rapid Rewards® Premier Credit Card ($99 annual fee) — This card is offering 40,000 bonus points after you spend $1,000 in purchases in the first 3 months. You'll also get 3,000 bonus points after your cardmember anniversary. You'll earn 2 points per $1 spent on Southwest purchases and Rapid Rewards hotel and car rental partner purchases. You'll earn 1 point per $1 spent on all other purchases.
  • Southwest Rapid Rewards® Plus Credit Card ($69 annual fee) — This card is offering 40,000 bonus points after you spend $1,000 in purchases in the first 3 months. You'll also get 3,000 bonus points after your cardmember anniversary. You'll earn 2 points per $1 spent on Southwest purchases and Rapid Rewards hotel and car rental partner purchases. You'll earn 1 point per $1 spent on all other purchases.

This article was updated to clarify that Southwest does not yet have scheduled redeyes returning from Hawaii, impacting connection options back to the mainland.

Additional reporting by Katherine Fan and Summer Hull; featured image courtesy of Marco Garcia / The Points Guy.

Featured image by Marco Garcia
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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