Posted in Airlines, Budget Friendly Travel

Flying Southwest Airlines to Hawaii

In January 2019, I signed up for a Southwest Rapid Rewards Credit Card. The main reason for doing so was that it came with a 1 year Companion Pass (plus 30,000 points) once you met a reasonable spend requirement.  In my original post (Southwest Card: New Sign-up Bonus) I stated that I would need to use the Companion Pass at least 3 times to make this choice worth giving up my last Chase 5/24 slot.

A few months later, Southwest began its new service to Hawaii. (Say Aloha to Hawaii on Southwest!).  I have managed to take three trips this year as planned. One to Portland, Oregon with my daughter, one to Texas with my husband and we just came back from Oahu, Hawaii!  For the Hawaii trip, I could fly my husband for just the cost of taxes and fees (about $45 total) and I used points to pay for my flights.  What a deal!

Southwest to Hawaii

I knew going into this how Southwest Airlines works.  They are an Economy Carrier so there aren’t any bells, whistles, or frills when you book travel with them.  But they are very affordable and overall a good airline.  Here are a few things that I discovered on our Hawaii trip.

Connections, Connections, Connections!

All Southwest flights to Hawaii currently leave from California.  We live in Michigan and there are no direct flights to OAK (Oakland) which is where we would be flying out of.  This meant that we had to book the trip as 2 segments, DTW to OAK and OAK to HNL, which required 3 planes each way to make the trip work.  On the way there, I was glad to be able to get our checked bag tagged at our DTW check-in for travel all the way to HNL (and it arrived just fine).  Coming back, we had to retrieve our bag in OAK and recheck it the next day.  Although our trip went pretty smoothly, this many plane changes adds some extra complexity and provides a lot of opportunities for a travel day to go awry.


Lining up the segments from Michigan to Oakland and Oakland to Honolulu was not easy.  We found all the schedules would require a layover in Oakland.  Our layover in OAK on the way over was 6 hours, which added to an already exhausting travel day.  We spent 23 hours getting to Honolulu from Detroit!  That’s a long day.  Oakland isn’t that interesting of an airport for spending that much time at.  No Priority Pass Lounge and terrible options for charging your devices (which you count on for entertainment on Southwest flights).

On the trip back, we arrived in Oakland around midnight with no flights leaving until the next day.  I booked a room at the Hilton Oakland Airport because they had a free airport shuttle and breakfast was included (if you are a Hilton Member…which we are).  This meant that our return travels stretched across 2 days to get us back into DTW where we finally landed around 11pm.

Secondary Costs

Even though our flights and bags were basically free, there were plenty of secondary travel costs.  Since these were long travel days and Southwest only serves snacks on their flights, we needed to grab some meals at the airport.  Airport food is never cheap!  From OAK to HNL and back Southwest does offer a “Snack Pack” which has some extra goodies in it. Still, since it’s a long day, you need something a bit heartier to get you through.


On our return flight, we were fortunate to be able to offset some dining costs with a visit to the Priority Pass Lounge in HNL and fuel up a bit before our flight departed.  This was not easy though,  because it required a shuttle from our terminal to the lounge and back.  We had to be very watchful of the time to be able to navigate getting the shuttle back to our Gate in time to board the plane. Sadly there was no Priority Pass Lounge in OAK where we spent the most time.

There was also a layover night in Oakland.  That meant we needed to book a hotel stay which cost $135.00.  I was lucky it included a free airport shuttle and breakfast, or those would have been extra costs as well.

Additionally, if we wanted decent boarding that allowed us to sit together, we would need to pay for Early Bird Check-in for each flight segment.  For us, that meant 4 segments at $25 each.  I had $75 in Airline fee credits left on my American Express, so I booked the Early Bird for the first 3 segments using that. I booked the same 3 segments for my husband by using 2 -$25 gift cards I had and 1 segment by using our Capital One Venture Card which allowed me to “erase” the charge with points.   That meant that we ended up with no additional cost.  Unfortunately, that still left one 2 flight segment we had to do regular check-in for (or pay the fees). That segment was for connecting flights, buying upgraded boarding before departure would have cost $30 for each part of the flight so for the 2 of us that would have meant an extra $120.  I decided not to spend the money so we were not able to sit together on either of those flights.   If we wouldn’t have had credits to use, we could have paid $100 per person for the ability to board early and sit together.

Thoughts Overall

We chose the money savings over the easier travel itineraries.  All of our flights went off without a hitch, but if you had one in there that was delayed, it could throw off the whole trip.  If we wouldn’t have had some points/miles options and Priority Passes, we really could have racked up some extra costs to make this trip work. It also took longer than booking direct flights with more expensive carriers.  Fortunately, we had enough time to allow for those long travel days.  We toughed out some inconveniences to keep our travel costs low.

Don’t be afraid to book a trip on Southwest to Hawaii. The 737-800’s we flew on between OAK and HNL were very comfortable.  They are expanding their options for airports they fly out of in California and fly into Hawaii.  Really look at the itinerary before you book any flights and make sure that all the pieces fit together nicely. Make sure the extra time that it takes to get there is worth the savings.

Southwest can be a very inexpensive option for Hawaiian travel especially if you have Rapid Rewards points to use or a Companion Pass. Just be sure to figure into your budget any extra costs needed for Early Bird Check-In, Meals, or Layover Hotels.  All and all we were able to make things work for us and we had a great budget trip on Southwest Airlines to Hawaii.


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!