Flying to Hawaii: Go Nonstop or Take a Break Halfway?

Monday's long-anticipated Southwest Hawaii routes left the travel community abuzz with fresh new beach plans for the spring, summer and fall. Whether you snagged one of Southwest's amazing launch deals or saved yourself a seat on a competing carrier thanks to attack fares, congratulations!

Unless you live in California, yesterday's Aloha deals probably meant you had to ponder the logistical question: Is it better to fly straight from Point A to Point B? What if it's cheaper or more beneficial to take a connecting flight, whether it's to earn twice as many segments for the same trip or just to save a few bucks? If you have kids or elderly travelers to consider, should you suck it up and push through, or give them a break halfway through the trip? With flight delays, cancellations and other snafus common these days, is it worth the risk of missing a connection?

Whether you're in the nonstop camp or on the layover bandwagon, it really comes down to [strong] personal preference, for the most part. We asked TPG Lounge members who live in cities with nonstop service to Hawaii to tell us: "Would you connect on the West Coast and fly in a 737 halfway across the Pacific to save $$ instead of flying nonstop? If so, how much of a price difference would justify it for you?"

Here's how TPG Lounge members make their scheduling decisions, in their own words.

For Angela B., it all comes down to the duration of the layover. As a rule of thumb, she'll take the travel interruption if it's less than two hours long, and the savings are greater than $200 per ticket.

Ricardo R. also put himself in the "price is king" bucket, calculating the savings from the perspective of out-of-pocket expense. "I'd say a max round-trip price [should] be $300 from LAX, or an airport nearby."

David A. is well aware that there's a sweet spot between savings and time cost. "Without [knowing] the numbers, it's not even worth answering," he told TPG. If the point of the layover is "to save $1000, yes. If it delays me 10 hours, no."

Meanwhile, East Coast-based Alexander M. has the value of his time calculated down to a science. "I fly from New York nonstop for around $850 on Hawaiian Airlines," he told TPG. "I'd need to save $400 to even consider a layover. I've done the layover route before and it makes a long travel day even more miserable." Raechel L. agrees: A fare "would have to be at least $400 cheaper" in order to make a stop worth her while. Ginger U. places an even higher value on the inconvenience of a travel pause: "Only if it saves $500 or more."

On the other hand, West Coast resident Antonia M. prefers the time of day that Southwest flights depart for Hawaii. "United [Airlines] flights were all nearly red eye or overnight from Hawaii to Portland, Oregon," she said. "So for me, Southwest [offers] a much better schedule, even with the need to layover in California."

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For Brittani S., comfort is the primary consideration, while discounts are just icing on the cake. And in Brittani's eyes, layovers are better than the direct-route alternative. "I have kids, so I try to aim for connections to break up the flights out of Hawaii anyway," she told TPG, so she can give them an opportunity to run around and work off some of that excess energy outside of a plane. "Southwest bringing the prices down is just a bonus." Chicago-based Sue V. agrees: "I always break it up," she said. "It's nine hours nonstop from Chi-town.

Julie M. also prefers to get there as quickly as possible. "I live on the West Coast and choose not stop from Seattle," she told TPG. "I'd rather be in Hawaii than in an airport or on a plane."

A number of Northeast long-haul travelers seem to appreciate the chance to stretch out a bit en route to the Aloha State. "I actually like stopping in LAX or SFO to stretch the legs for a brief layover from the East Coast to Honolulu," said Jim K. and Michael S.

With specific peak-season trip dates, Michael G. had cost as his top priority in mind. Flying from Amarillo, Texas (AMA) to Hawaii in June would cost about $1,800 less on Southwest, he told TPG, connecting through Oakland instead of traveling on American or United Airlines via alternative airports in Dallas, Houston or Denver.

Fraser M. would prefer to fly direct, but options are limited and expensive from Georgia. Flying Southwest to Hawaii from Atlanta "requires another night of hotel on the return trip, and I have three kids," he told TPG. "No, thanks. Unfortunately Delta knows that and it's hard to get a flight out of here for under $1,500. ☹️"

Jeffrey S. is familiar with the process of getting to Hawaii from Texas, so he decided it wouldn't hurt to compare service on Southwest. "I live in Dallas-Fort Worth (DFW) and am usually headed to Kona (KOA), so I have to change planes on American Airlines anyway to get there," he said. "I figured I'd try the Southwest service when it posted today, and I got a $98 round-trip fare from Oakland (OAK) to Honolulu (HNL). We'll spend the weekend in San Francisco first, making that connection worthwhile for some fun."

Meanwhile, John J. didn't even engage with the initial question. "I'd pay more not to fly Southwest any day," he flatly said.

On the flip side, Andrea J. couldn't have pulled the trigger on launch-day fares more quickly. "[Having the] Companion Pass and Rapid Rewards points make this a no-brainer."

Regardless if your next jaunt to Hawaii takes one stop, two — or three, you'll want to keep in mind that hiccups can happen, especially with Southwest's first-time foray into offering overwater routes, coupled with a shortage of aircraft in service. Don't forget to pay for your trip with a card that offers travel protection, and consider purchasing independent travel insurance if you book excursions, hotel rooms and similar non-refundable plans that could be affected by delays. And if flying Southwest, remember that the low-cost carrier doesn't offer hot meals on board, even for purchase: Buy food ahead of time, or pull out your Priority Pass for a free airport meal.

If you're traveling with small kids, Mommy Points recommends stopping on the West Coast to ease some of the misery from time changes and red-eye schedules.