ALOHA! It’s been a bit since Southwest started their Hawaii flights and I want to tell you all about it so hopefully, you can enjoy it soon!

My husband and I headed from our hometown in Indiana to Maui to attend a Southwest All-Access Event and here’s what it was like.

Maui Hawaii rainbow
Beautiful Maui


Getting to Hawaii on Southwest From the Midwest

Cami Southwest Companion Pass

Flying to Maui from the Midwest is a long haul, but thankfully it’s possible. We had our choice of times to depart but they were all VERY EARLY in order to get us to San Jose in time for our flight to Maui. 

I wasn’t looking forward to checking in at 6:30 a.m. the day before our flight (24 hours ahead of our departure), but because I was so excited about the trip, I ended up waking even earlier!

Our flight departed the next day from Indianapolis (my Southwest home airport) to Denver. When we arrived in Denver, we were supposed to stay on the same plane, but they ended up moving us to a different one.

We had no boarding passes for this flight, so we wondered, how would we board? Turns out, they allowed us to board right after the pre-boarding folks by showing our photo IDs. Easy peasy and a great selection of seats, of course!

From Denver, we flew to San Jose, California, from which we’d fly directly to Maui. The San Jose Airport is very small with only 30 gates and no additional security required, so it was easy to navigate.

We made our way to the Priority Pass Lounge to use two of our 10 yearly free passes that we get via an card_name. Since I knew we wouldn’t be served an actual meal on the flight, I wanted to be sure I wasn’t hungry, as it would be at least six hours before dinner. In the lounge, we knew we could relax for a bit in the quiet and recharge our phones as well.

If you hold a Priority Pass Select membership via the card_name card, you can also take advantage of the lounges here. Check out Lyn’s hack to save on drinks for the plane using her Priority Pass Select!

Flying From San Jose to Maui

Southwest Max 8 plane

We boarded the flight from San Jose to Maui around 11:30 a.m. in A-30+ positions, so there was no problem getting seats together. In fact, the plane was only half to two-thirds full, so the crew actually had to monitor where everyone sat for proper weight distribution for take off!

The plane Southwest flies to Hawaii currently is the Boeing 737-800. Check here for the seat map so you can scope out your best seating option. For this longer flight, you might want to go for the exit row seats!

Be sure to check in exactly 24 hours in advance to get the best possible boarding position. 

This plane is modern with Southwest’s new interior design, including 175 of the 32-inch pitch seats, more legroom and three bathrooms. The sloping overhead storage bins and sculpted, lighted ceiling leave the plane with more of a wide-open feel, which is nice for longer-haul flights.

Southwest heart logo

You might be greeted, as I was, by flight attendants wearing leis, Hawaiian aprons and frangipani flowers in their hair. Yes, you really ARE on a flight to Hawaii! 🙂

Southwest Airlines Hawaii
Credit Southwest Airlines

Don’t forget to load the Southwest app before take-off, so you can watch their free TV shows, movies, flight path, music, weather and more. Also, while in airplane mode connected to their signal, you can send messages via WhatsApp or iMessage (this is if you have an iPhone and are sending messages to another iPhone connected to WiFi). And, if available, for $8, you can purchase their satellite-based WiFi to surf the net from the clouds :).

Here’s everything you wanted to know about Southwest wifi and entertainment options.

We grabbed a seat near the back, as I never like to sit over the wing because I want to see the sights along the way like the view below. Ahh…

Southwest wing Hawaii

Soon after take-off, the flight attendants came by with the drink cart. You can choose from their free drinks with Hawaii flights serving an additional one–a special pineapple orange blend juice as well.

If you’d like to purchase an alcoholic drink (here are 5 ways to try to get free drink coupons from Southwest), a Kona Longboard Island Lager and Blue Chair Bay Coconut Spiced Rum are specials just on Southwest’s Hawaii flights to put you in the Aloha spirit.

Southwest Hawaii alcoholic beverages

Southwest planes don’t serve a meal even though you’ll most likely be on board when you’d normally be eating. They do serve a larger-than-normal snack box, which includes Wheat Thins, white cheddar cheese spread, pretzels, fruit snacks and Tic Tacs. But if that’s not enough to tide you over, don’t forget to bring your own snacks!

Later in the flight, the crew will also serve you a package of Milano cookies and offer water or coffee to go with it to help you make it until you land.

Southwest Hawaii snack pack

The time passed very quickly for me, as I read a book and then watched a movie. Soon enough, they said we were about to land. Then the beautiful coast of Hawaii came into view!

The gorgeous waters surrounding this tropical paradise and the sand along the shore are sure to catch your eye, but don’t forget to look above the cloud layer, to try to spot the summit of Haleakala in all its glory, if flying into Maui!

Southwest wing Hawaii Maui beach


Flying Home From Hawaii on Southwest

Returning to the Midwest, as is the case for those flying to the eastern half of the U.S., we had to stay overnight in California. This is because Southwest doesn’t operate “red eye” flights (overnight flights), and it’s impossible for them to get you from Hawaii in the morning all the way to the other side of the U.S. (which is six hours ahead) by day’s end.

We left Maui at 4 p.m. and got to San Jose and into our room at around midnight. We then got up at 4 a.m. to catch our 7 a.m. flight back to Indianapolis. Remember, you’ll need to plan an extra night when booking flights if you live in the Midwest or further east.

Our adventures in Maui were certainly worth all the flights and overnights. Have you booked your Southwest flight to Hawaii yet?

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  • Cami Sauder

    Cami Sauder, a member of the Families Travel Free team, is a longtime traveler who aims to be away from home at least 1/3 of the year. She's mastered the art of using miles and points to save on flights and hotels and saved more than $16,000 on travel using points in the last year. She and her husband have a goal to see as many National Parks as possible.

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