This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. For an explanation of our Advertising Policy, visit this page.

Southwest began selling tickets to Hawaii this week, with initial $49 fares to Honolulu (HNL) and Maui (OGG) scooped up in the blink of an eye. It’s big news for sun-starved flyers in California, where flights are set to begin from Oakland (OAK) and San Jose (SJC) on March 17, 2019 and May 5, 2019, respectively.

But what about everyone else? We pushed Southwest’s booking portal to its limits testing out possible routing options from other West Coast cities, the American heartland and the Eastern Seaboard. While we did find availability from cities like Orlando (MCO), Atlanta (ATL), New York (EWR), Austin (AUS) and Chicago (MDW), getting back wasn’t as simple.

Overnight Flights on Southwest? “Not Right Now”

sunset-maui-ogg-hawaii
If you’re watching sunset in Maui, your Southwest flight back to the mainland already left (Photo by Darren Murph / The Points Guy)

Across the board, Southwest’s ticketing engine throws up zilch when it comes to flying from Hawaii back to the mainland east coast, and with few exceptions (Chicago), fliers everywhere east of the Pacific time zone are left hunting for a different carrier if they intend to return.

The reason? Southwest doesn’t do red-eye flights. It never has, and while launching flights to an island chain some 2,500 miles away from the mainland United States feels like the ideal catalyst, it’s simply not in the cards.

I spoke with a Southwest representative following the debut of ticket sales to Hawaii, and was told that while the airline would “never say never” to flying overnight, the answer unambiguously was “not right now.” Moreover, I was informed that Southwest’s cone of connectivity for Hawaii is intentionally limited to the region west of the Rockies (plus Denver), and that the airline is not marketing service anywhere beyond that.

To clarify, it’s not because Southwest can’t operate red-eyes. There is no technical reason why the airline can’t schedule an overnight flight (unlike ETOPS certification, which it did need to fly to Hawaii). The airline grew up as a short-haul carrier, and it has grown its network by targeting destinations that did not require flying at times the only thing open is the local IHOP and legacy airline operation centers.

Hawaii’s Reliance on Red-Eyes

Views of O
Views of O’ahu, departing from HNL (Photo by Darren Murph / The Points Guy)

Those situated east of the Rockies have precious few options when it comes to flying back from Hawaii. If they leave on a daytime departure out of the islands, they’ll often land in California, Oregon or Washington at night, requiring a red-eye flight from there home to avoid a one-night stay in either a hotel or airport lobby.

Alternately, you can fly overnight (e.g. red-eye) from Hawaii on carriers such as Alaska, American, Delta, United and Hawaiian, putting you back on the US West Coast in the wee hours of the following morning. From there, it’s a bleary-eyed daytime flight back home.

delta-plane-airplane-jet-maui-ogg-airport-kahului
A Delta jet awaits departure from Kahului Airport in Maui (Photo by Darren Murph / The Points Guy)

A few carriers offer long-haul red-eye flights from Hawaii, such as Delta’s routes from Honolulu (HNL) to Detroit (DTW), Minneapolis-St. Paul (MSP) and Atlanta (ATL) and United’s nonstop service between Honolulu (HNL) and Newark (EWR). Hawaiian will begin flying a red-eye between Honolulu (HNL) and Boston (BOS) in April 2019, creating the longest domestic flight in the entire country.

Given that Southwest’s initial service to Hawaii will begin and end in two California airports, connection options that don’t require overnight layovers are nonexistent. Southwest could conceivably get East Coasters back home from Oakland (OAK) and San Jose (SJC) if it began flying red-eye flights out of Honolulu (HNL) and Maui (OGG), but it’s evidently OK with leaving that business to other airlines.

Bottom Line

Haleakala National Park Maui - crater hawaii view
Maui’s Haleakala National Park is calling (Photo by Darren Murph / The Points Guy)

If ever Southwest was to ponder its first overnight flight, launching service to Hawaii would be it. Considering that it has steadfastly refused to introduce overnight flights even after its debut in the 808, we’d say it’s very unlikely the airline will change course in the near future.

Because of this, central US and East Coast flyers should essentially cross Southwest off of their list when it comes to flying to Hawaii. The only sensible use of Southwest to Hawaii for those situated east of the Rockies is to create a trip within a trip — not a bad idea, but definitely a time-consuming one. For example, fly to California for a few days, enjoy Yosemite and In-N-Out, then continue on to Hawaii. For the return, you’d need another pre-planned stop in California, or look to points and miles for cheap one-way returns on a legacy airline.

Of course, we always recommend you keep an eye on TPG‘s Deals page, where we frequently post about sales to paradise.

Featured image by Marco Garcia / The Points Guy

Know before you go.

News and deals straight to your inbox every day.

2018 TPG Award Winner: Mid-Tier Card of the Year
Chase Sapphire Preferred® Card

NEW INCREASED OFFER: 60,000 Points

TPG'S BONUS VALUATION*: $1,200

CARD HIGHLIGHTS: 2X points on all travel and dining, points transferrable to over a dozen travel partners

*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.

Apply Now
More Things to Know
  • Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $750 toward travel when you redeem through Chase Ultimate Rewards®
  • 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards. For example, 60,000 points are worth $750 toward travel
Intro APR on Purchases
N/A
Regular APR
18.24% - 25.24% Variable
Annual Fee
$95
Balance Transfer Fee
Either $5 or 5% of the amount of each transfer, whichever is greater.
Recommended Credit
Excellent/Good

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

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.