Posted in Airlines, Budget Friendly Travel

Why We Are Flying Southwest Airlines to Hawaii…Again!

Southwest Airlines added routes to Hawaii in early 2019. I had a companion pass and a bundle of points, so we took a chance and booked a trip for that October. Although it was certainly a cheap option, we found out that it was a bit clunky to manage. Three years have gone by and as we booked our current trip with them we were hopeful that they had simplified some aspects of the process.

That would be a hard NO! You can do it cheaply, but it won’t be easy.

No Direct Connections from East Coast

When Southwest first began flying to Hawaii in 2019, all of the routes originated from one of 3 airports in California. There was no option to book a flight to Hawaii from any other location that would include the proper connections. This meant that you needed to find your own separate positioning flights to one of their origin airports. Because we travel out of Michigan this meant booking 2 separate flight segments each way. One from DTW to OAK and another from OAK to HNL and then reverse for the return trip. Because these were separate segments and not a connection, getting them to line up was tricky.

Since our first trip to Hawaii on Southwest, they have added more point-of-origin cities in California in addition to departures from Phoenix, Arizona, and Las Vegas, Nevada. However, the number one thing I had hoped for was that they would eventually offer their own connecting flights. That still hasn’t happened, leaving customers with the burden of trying to independently line up positioning flights to Southwest origin cities.

Number of Flights

We have established the fact that unless you are coming from the West Coast, you will need to book 2 separate flight segments. But you may also have plane changes within those segments. We can’t fly to any of the California airports that service Hawaii from Michigan without changing planes at least once. That puts us at 3 different flights each way.

Our Current Flight Itinerary

  • DTW > SJC with a plane change at MDW (1 hour)
  • 2 Hour Layover at SJC
  • SJC > OGG Non Stop
  • After a few days in Maui we hop to Oahu OGG > HNL
  • HNL > OAK Non Stop
  • Overnight Layover OAK
  • OAK > DTW with a plane change in STL (3 hours)

Another thing to keep in mind is that all of those plane changes mean opportunities for missed connections due to flight delays or lost bags. Multiple boardings on flights without assigned seating can be frustrating and involves putting your bag in the overhead bin and getting it down several times. No big deal for some folks, but I am 5’0″ tall. If I am not traveling with my 6’1″ husband, it’s not that easy for me to do.

Southwest allows passengers to check two bags free. I appreciate having that option without needing to pay additional fees. For our last trip, we each took a carry-on plus checked one large bag that we shared. The Southwest Gate Agent at DTW was able to tag our checked bag with all of our transfers and amazingly it managed to arrive with us at our final destination. With current airline issues and staffing shortages, I am not sure that I trust that would happen today, so we have decided for this trip to keep it simple and travel with just our carry-on bags.

What to expect or not expect when flying Southwest

  • Southwest is an Economy Carrier
  • No seat assignments (but you can pay extra for an early boarding position)
  • No seatback entertainment (but you can watch content on your device)
  • No power ports for charging devices at your seat
  • Limited food and beverage service
  • Seats that are at an economy comfort level

Plan, Plan, Plan…

When traveling on Southwest with other people, I usually purchase the Early Bird boarding. Since they don’t assign seats, Early Bird boarding eliminates some stress and helps ensure that co-travelers get to sit together. To offset the cost of the Early Bird Boarding, I suggest using a credit card that has an airline fee credit or allows you to erase the purchase with points.

There are no plugs or charging ports located at your seats on Southwest flights. If you plan to use your own device to stream content, ensure it is fully charged before leaving the airport! Connect to their site and/or download any content that you plan to watch before takeoff. In preparation for our upcoming trip, I have downloaded a new audiobook and have a few streaming apps set up on my device.

For long travel days like a trip to Hawaii, plan to grab some food in between flights if you can. We have Priority Pass lounge access, so I like to check the connection airports to see if they have a lounge available. Lounges are more relaxing than hanging out by the gate and save you money since they offer complimentary food and drinks. Because Southwest is a budget carrier, its gates are generally not located very close to lounges. If you plan a visit to a restaurant or lounge while in the airport, make sure to allow enough time to get there, have a snack, and then get back to the gate before it’s time to board your next flight.

For our upcoming trip to Hawaii, we change planes in California going each way. On the way there, we have a 2-hour break in San Jose which will allow us to get off the plane, visit the restroom, grab a bite in the lounge, and stretch our legs a bit. Coming back our plane lands in Oakland after 11 pm. Since there are no flights until early the next morning, we booked a hotel (that offers a free airport shuttle) for the night. This nicely breaks up a long travel day in less than comfortable economy seats.

So why are we flying Southwest to Hawaii again given that it’s not ideal?

If you read my last post, Utilizing Large Purchases to Earn Travel Rewards, you know that we are in the midst of planning a wedding for our daughter. Weddings are expensive, especially with the inflated prices we are seeing right now. Since we had a lot of points, miles, and travel credits available, we decided to plan a budget trip.

I love the thrill of finding a good deal on travel costs like hotels, car rentals, and airfare so that we can spend more on food, fun, and entertainment during our vacations. For this trip, we have managed to be Boujee on a Budget landing great car rental deals (thanks to Autoslash) and securing 2 top-notch hotels using points. We sacrificed a little on comfort and convenience by flying Southwest because we couldn’t beat the cost. I booked our flights early during one of their fare sales, combining Southwest points, travel funds, and other credit card benefits. The final cost for all of our flights and Early Bird boardings was only $374.58!

Southwest set up their Hawaiian route plans very similar to those at Hawaiian Airlines. Both carriers only offer flights from a limited list of origination cities and require passengers to find their own positioning flights. Passengers may then choose to use another airline for those flights. Southwest and Hawaiian Airlines are potentially missing financial opportunities by not providing direct connections, which would mean keeping more passengers on their airlines for those initial segments.

Maybe now that travel is returning to pre-Covid numbers, Southwest will take a look at how they can make it easier for customers to navigate their Hawaiian routes. But something tells me that it is what it is. Ultimately the choice is ours. Book cheap flights with Southwest that are a bit clunky or pay more to go with a big carrier and avoid the hassles.

Dream, Plan, Save, Adventure!


Just an Art and History Nerd from MI Who Loves to Travel, Explore, Save Money, Share Tips, Enjoy the Best Foods & Adult Beverages🍷🥂🍸 Then Blog About It!