Remember that saga from earlier this year where I had a tough time using my Alaska/Hawaiian companion fare but finally got it worked out? That was for a long-planned family vacation in Hawaiʻi. Yes, I was just there a month earlier, but that was for work. I know, you’re thinking, “this’ll be another boring Hawaiian trip report,” but you’re wrong. Pretty much everything went wrong on the way out, and we never even ended up on the airline. Hawaiian really screwed this one up, then American created their own mess, and finally… Southwest saved the day.

We were booked to fly from LAX to Honolulu on the 7am departure and then connect to Hilo for a few days, exploring the windward side of the Big Island. We had the morning flight booked with a 1.5 hour connection, which seemed ideal. Then there was a schedule change a couple months before travel, and our connection was canceled. We were looking at a long 2.5 hour connection. We could leave LA on the 10am, have an hour and a quarter in Honolulu, and get into Hilo only an hour later, so we made the switch — after yet another pained conversation with a Hawaiian agent. That was a mistake.

Fast forward to the day of travel. I had woken up leisurely around 6:30am for that nice and late 10am flight when I saw a notification on my phone. Boarding had been delayed until… 5:15pm? I rubbed my eyes to make sure I wasn’t missing something, but sure enough, we had been delayed eight hours to 6pm. Great.

First thing I did was hop online to get the lay of the land. With this delay arriving into Honolulu so late, there were no connections on to Hilo. Even worse, there were no flights from Honolulu to Hilo with four seats the next day either. Naturally, I started scanning for Kona options as I called up Hawaiian, deciding a 2+ hour drive would be better than delaying yet another day.

As usual, I was sent to that awful call center in the Philippines. I don’t understand why that still exists considering it’s the same reservation system as Alaska. The person on the phone said she could look at other options for me, but every 30 seconds she kept saying she had to go ask her colleague for help.

I had found a flight at 1:30pm on American to Kona that had decent availability, so I asked her to move us to that. After talking to her “colleague,” she said they wouldn’t put me on another airline. This made no sense, because it was showing as a maintenance delay. (I actually looked it up, and the flight out the night before turned back to LAX, so they stole our airplane for the 7am flight we were originally on, and the 10am got stuck with the broken plane.)

The agent then asked if I could fly out of a co-terminal. I said yes, but there weren’t any flights that I could get to in time that had availability. (Long Beach was pushing it, but it was ful anywayl.) She would not stop asking about co-terminals and asked if I could fly out of Seattle or San Francisco. At one point she asked if Sacramento or Oakland would be possible.

At this point, I’ll admit that it got heated. I told her those were nowhere near us, and I needed real solutions before seats disappear. She just kept saying I could get a refund. That was all she was willing to do.

I should have hung up and tried someone else. Actually, I should have hung up and called Alaska to talk to someone in Boise, but the available seats were dwindling. I told her to just refund our outbound, and then I bought tickets on American for a little over $300 each.

It took her a long time, and we were on the phone for more than an hour before she finally got it done. Or she said she got it done, but then I looked online at the reservation and saw she had only done one. Eventually, she got it done.

With our new American flight confirmed and time to kill, I did call Alaska directly and asked them to look at the reservation to make sure our return looked ok. I did not want this mistake to screw us. The Boise-based agent said it was good. (It wasn’t, but that wasn’t apparent until the next part of our trip, so stay tuned for that.)

Just when I thought I could relax, American delayed our new flight by 3 hours. It was an aircraft swap, and our new airplane was in Philadelphia — but it hadn’t even left.

This was not great. I had quickly switched the rental car to Kona, but we still had a more than two-hour drive to where we were staying. We would arrive at 7:30pm which meant stores would be closed, and we’d be driving on a very dark saddle road that climbs above 6,000 feet across the island. If we were lucky, we’d get to our Airbnb at 11pm. On top of this, I didn’t believe the posted departure time since it would require everything to go right in Philly and still only be a 35 minute turn. Yeah, right.

So it was back to the drawing board, and that meant flying the next day. Sure enough, Southwest had a weekend-only 7am flight from LAX to Kona, and we could book basic economy for $282 each, only about $70 more per person than what we originally paid including the checked bags. We’d land at 9:30am and then be on the Hilo side for lunch. Done deal.

And I’m glad we did. That American flight? It showed the inbound arriving at 4:54pm for a long time… with a 4:45pm departure to Kona. Typical American. It was eventually pushed and didn’t leave until 6:15pm. It would have been a very late night… but not as late as if we’d stuck with Hawaiian. Our original flight ended up delaying 14 hours, leaving after midnight for a westbound redeye.

I checked us in on Southwest right away. Since it was basic economy, we were placed in 27EF and 29AB, just in front of the last row. This seemed perfectly fine to me, so I didn’t bother paying for seats further forward. After an early night, we woke up before 5am, got our stuff together, hopped in a Lyft, and made our way to LAX.

The traffic was fine, but the line to drop a checked bag? It was long.

We printed our own tags and got in line, but it took 20 minutes before we reached someone to give our bags. And when we were done? The line had gotten much longer. Yikes.

We went through security about an hour before departure, and then we headed to the gate. Our airplane was there, and they said we’d start boarding soon. I relaxed as the kids went to get snacks. Then, I tensed up. The gate agent said they were still waiting for one more flight attendant, so boarding would be a delayed a bit. But to pass the time, she said that people probably noticed she had an accent. She gave her name, and then said the first person to guess where she was from would get a $50 gift card on Southwest.

I was shocked that it didn’t take long for someone to guess Lithuania correctly. Impressive. But by the time that was done, the last crewmember had arrived, and we were boarding. Well played.

As boarding began, they called my name. Uh oh. Turns out, they said we could do priority boarding. Something smelled fishy. I had been talking to a friend at Southwest as I went through the mess the day before, and he knew I ended up booking Southwest in the end. Apparently, he said something and this got me a little bit of special treatment. You know I never want that, but after this long saga, I didn’t mind as much as I normally would.

Walking down the jet bridge, someone from the station gave me a bottle of Korbel, saying thanks for writing about the airport’s people mover saga. Ok, well… that was nice. Thanks for reading.

Southwest 2637
August 2, 2026

Stepping onboard, I was greeted by a very nice and new-looking cabin with those big bins (which I didn’t need since I checked my bag). These MAXs are really like flying a different airline than those old -700s. We trudged toward the back and took our seats. Randy was working in the back, and he had help from Steve who was a flight attendant commuting back home. Randy took my champagne and said he could keep it cold for me.

This airplane had the older seats which have the fast USB charging port but don’t have the device holders.

They boarded pretty quickly, and we pushed back a minute early. Then, as always, it was a quick taxi to the runway. The captain had jokes, and told us all it would be a short 5 hour and 5 minute flight to Buffalo. But he wasn’t joking when he said we’d have a mostly nice ride to Kona after our climbout.

We had Anuvu wifi on this flight, which meant I didn’t plan on having wifi. But I logged on with my phone and it actually worked ok for limited uses. I ended up watching a movie anyway, The Devil Wears Prada 2, because, well, can’t imagine there’s any other time I’d ever watch that movie.

At altitude, the flight attendants got up and came through with drinks. They had a jumbo snack box with multiple options and told everyone to take as much as we all wanted.

I raided those snacks like I was preparing for a nuclear winter. Then I got the whole can of water, and I sat back and watched my movie.

Along the way, we passed by Hurricane Genevieve which I think was only a Tropical Storm by that point. We skirted to the north and had just enough bumps for the seatbelt sign to flip on.

I went back to use the lav, and that’s when I chatted with flight attendants Randy, Steve, and Carissa. Randy and Steve had been with Southwest for more than 30 years. Carissa was pushing four. We talked shop for a little while.

While I was back there, they did a second pass for drinks in the cabin. Carissa said she could whip up something for my kids, so she did something that she said was like a creamsicle and another that was a strawberry refresher.

My kids weren’t interested, but I was. That strawberry refresher was good.

Around an hour before landing, they came through with the third service which included drinks and a package of Oreos. I just kept writing until it was time to descend, so we could finally, properly start our vacation.

Once Mauna Kea came into view, I knew we were almost there. Flying into Kona from the north, we had great views the whole way. And the flight was apparently so pleasant for our pilots that they decided to do a go-around, which I caught on a time lapse video.

After we climbed back up and pointed north, the captain told us that approach control kept him too high for too long. I think he just liked the view. After a quick circle, we touched down and rolled out toward the end of the runway where a Boeing 777X was sitting, wings folded, apparently doing some testing.

After we blocked in, the best news for us sitting in the next to last row was that they would be using both the front and back doors. We were off quickly, and then, to cap off the special treatment, some of the local Southwest rampers met us and gave us leis and some swag bags with water bottles, a coozie, and maybe a couple other trinkets.

Again, I never like special treatment, but I haven’t been lei’d upon arrival in Hawaiʻi in so many years — and I was so exhausted after that epic 24 hours — that I was very happy to accept and kick off our trip right.

We rented a Bronco and spent a compressed 2.5 instead of 3.5 days going everywhere from the southern tip and the green sand beach of Papakōlea…

… to the top of Maunakea.

It was exhausting to cram that into three days, but we did it. Then it was off to Maui.

This is the second time Southwest helped save a Hawaiian vacation for me. The first was when my Hawaiian A321neo from Kahului to Long Beach was canceled at the last minute due to the engine fiasco in 2023, and I bought a last minute ticket to LAX. Maybe I should just be buying tickets on Southwest in the first place.