Should Southwest Airlines Operate Red Eye Flights For East Coast Passengers?

Perhaps the biggest aviation news to come recently was the launch of Southwest’s flights to Hawaii. After some initial route proving flights, ticket sales were up soon. With great low fares, this was an excellent chance to book a leisure trip to a vacation hotspot. While Southwest is a welcome entrant in the market, some passengers aren’t feeling the hype surrounding this launch. Here’s why.

Southwest is now flying to Hawaii! But not all of Southwest’s flyers will be able to make it to Hawaii.

Southwest did something a while back. They decided not to operate redeye flights and don’t allow for overnight connections. This creates a bit of a problem for travelers to Hawaii.

If you read my Ultimate Guide to Southwest Hawaii Flights, you’ll recall that availability from the Central and Eastern areas of the United States to Hawaii on Southwest was nonexistent or incredibly limited in options. To understand why, let’s look at some of Southwest’s flight times.

Southwest Hawaii Flights and Connections


Southwest flight schedules from Honolulu to Oakland. Screenshot: Southwest Airlines Website
Southwest flight schedules to San Jose. Screenshot: Southwest Airlines Website

Connecting to Hawaii might not be a problem for most, but the issue comes with the return flight. As you can see, the earliest you would get into a major Southwest “hub” like Oakland or San Jose would be at 5:50 pm. If you’re looking to fly off to places like Atlanta, Chicago, or Houston, you don’t have any options to make connections until the following morning.

Since Southwest Airlines doesn’t sell tickets with overnight connections, your flight won’t be on one reservation. Because airline ticket pricing can vary, chances are, you could be parting with more money than you anticipated on Southwest in addition to a stopover in California. Let’s say you decided to book two separate legs. One direct from your preferred airport to Honolulu with a layover in Oakland. On the return, you could book one leg to Oakland. Spend the night in the area, and then a second leg from Oakland to your preferred departure airport. In addition to spending an extra night in travel, some might find it annoying that they have to re-check bags or depart from Hawaii a day earlier to make it home in time.

Some may appreciate Southwest’s baggage allowance, but not appreciate the potential need to recheck bags on a multi-city itinerary. Photo: Southwest

For some people, it might just be better to fly a carrier like Hawaiian Airlines from farther, East Coast destinations to Honolulu for marginally more in order to save time on travel.

Those looking to escape the Northeastern or Midwestern U.S. winters might find their options on Southwest to be limited.

In addition, airline loyalty programs and co-branded credit cards can make flying in coach a better experience for many travelers with features such as lounge access or waived checked baggage fees for the cardholder and companions.

That leads us to the big question:

Is Southwest Airlines any better for flying to Hawaii if you live on the East Coast?

Ultimately, the answer to this question is up to each passenger. Some passengers will swear by Southwest and find some benefits on Southwest that they would absolutely hate to fly without. Others might not see the value in flying Southwest.

On given dates out of Boston, New York, Dallas, and Chicago, one can find flights to Hawaii (including nonstop flights) for between $500-$600USD in coach. Even smaller markets like Nashville, Raleigh, Milwaukee, Austin, and St. Louis can see flights to Hawaii for between $500-$600 USD in coach. For some, these flights might just be easier since they’re all on one round trip reservation with no stopovers, only layovers that could save precious vacation time.

Ultimately, it would seem smart for Southwest to change their policy on redeye flights and bring passengers back on a nighttime hop to the mainland so they can make connections back home. Most of Southwest’s passengers are going to be leisure passengers who would definitely appreciate another day in Hawaii. After all, who wouldn’t love to spend another day on the beach?

Do you think Southwest should start flying redeye flights? Would you fly Southwest if they offered connecting options? Have you booked a multi-city flight to Hawaii on Southwest? Let us know in the comments!

1 comment
  1. East Cost? Do you guys know what proofreading is? Reading some of your articles feels like they were typed on Enigma machine.

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