The day we’ve all been waiting for! In what was probably the most talked-about expansion in the past few years, Southwest has finally gone live with flights from the lower 48 to Hawaii. Maybe we’ll even see a bit of the “Southwest Effect” for the Hawaiian market.
Image courtesy of Pixabay SocialButterflyMMG
All Southwest flights to Hawaii will originate in California – here’s the full list of direct flights:
- Oakland (OAK) to Honolulu (HNL) starting March 17th; prices starting at $49 one way or 1950 Rapid Rewards
- San Jose (SJC) to Honolulu (HNL) starting May 5th; prices starting at $49 one way or 1950 Rapid Rewards
- Oakland (OAK) to Kahului (OGG) starting April 7th; prices starting at $49 one way or 1950 Rapid Rewards
- San Jose (SJC) to Kahului (OGG) starting May 5th; prices starting at $49 one way or 1950 Rapid Rewards
As well as some inter-island routes:
- Honolulu (HNL) to Kahului (OGG) starting April 28th; prices starting at $29 one way or 1379 Rapid Rewards
- Honolulu (HNL) to Kona KOA starting May 12th; prices starting at $29 one way or 1379 Rapid Rewards
(This is HUGE news for people with the Southwest Companion Pass!)
Southwest has some Growing Pains
Southwest has undergone a lot of expansion in the past few years, and has had it’s fair share of growing pains. With the acquisition of AirTran, the big red and blue planes began flying internationally, throughout the Caribbean and Central America. For the past year, they’ve stayed in the news with their plans to fly to Hawaii. Late in 2018 the airline secured gates at major airports on multiple Hawaiian islands, and just recently received final ETOPS approval from the FAA.
These flights are SUPER cheap. I have to assume that this is just introductory pricing, and Southwest is trying to capture market share from the other guys. Under $100 roundtrip west coast to the islands, with free checked bags? No way that lasts…
This is great for folks on the west coast, but there are still a few kinks to work out. Southwest’s booking system still won’t let you book an overnight stop. That means it’s nearly impossible to book a roundtrip on Southwest from the east coast. Either you’ll have a super tight connection, or you’ll need a positioning flight. My recommendation is to book a one-way to the West Coast, hang out for a night in the Bay Area, and then continue on to the islands! From my home airport of Boston Logan, I’d be looking at 2 stops both ways, I’ll wait this one out.
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
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