Personal Finance Insider writes about products, strategies, and tips to help you make smart decisions with your money. Business Insider may receive a commission from The Points Guy Affiliate Network, but our reporting and recommendations are always independent and objective.
ohrim/Shutterstock
- Southwest Airlines launched its inaugural flight to Hawaii from Oakland to Honolulu on March 17, 2019. New routes have already been announced and will depart from San Diego, Los Angeles, Ontario, Long Beach, Orange County, Oakland, Burbank, and San Jose.
- Southwest Airlines offers a robust airline loyalty program with no blackout dates, two free checked bags per person.
- Points that are easy to earn through Southwest credit cards like the Southwest Rapid Rewards Priority Credit Card and Southwest Rapid Rewards Premier Credit Card, or non-branded cards like the Chase Sapphire Preferred Card or Chase Sapphire Reserve.
- Want even more free flights to Hawaii this year? Consider earning the Southwest Companion Pass - a perk that lets your designated companion fly free whether you pay in cash or miles.
In early 2019, Southwest Airlines finally got approval from the FAA to begin its new routes to Hawaii. The airline's inaugural flight to paradise took place on March 17, 2019 out of Oakland, California, lasting 5.5 hours before landing in Honolulu.
And now a new era in travel to Hawaii to begins. With Southwest Airlines now offering affordable Hawaii flights with two free checked bags and free cancellations on many of their fares, many expect other airlines with routes to Hawaii will be forced to adjust pricing downward to compete.
Before you plan your next trip to a gorgeous destination like Maui, Honolulu, or Kona, it's crucial to know all you can about the new flights from this discount carrier. Here are the main details to be aware of, along with what you can do to score cheaper flights - or free flights - for your next vacation.
Routes to be aware of
Southwest's initial plan for Hawaii includes nonstop flights from several California airports including Oakland, San Jose, Los Angeles, Orange County, Long Beach, Ontario, Burbank, and San Diego. However, flights to Hawaiian destinations will vary by departure airport and be rolled out slowly over the next few months. Here's a timeline for each of the new flights:
Oakland:
- Flights to Oahu (HNL) started on 3/17
- Flights to Maui (OGG) started on 4/7
- Flights to Kona started on 5/12
San Jose:
- Flights to Oahu (HNL) started on 5/5
- Flights to Maui (OGG) will start on 5/26
- Flights to Kona started on 5/12
Los Angeles, Ontario, Orange County, Long Beach, Burbank, and San Diego:
- Flights to Oahu (HNL) started on 3/24
- Flights to Maui (OGG) started on 4/28
While the flights above can get you to Hawaii without any stops, you can also book connecting flights from most airports where Southwest flights are available. Also note that even more routes could be announced soon.
A whole host of inter-island flights also launched on April 28th, including daily round-trips between Honolulu and Kahului. Flights between Honolulu and Kona also launched on May 12th.
In terms of the airplanes you'll fly to cross the Pacific, Southwest announced in a March 13th press release that it has temporarily grounded all its 737 MAX 8 Aircraft due to ongoing safety concerns. This means you'll likely be flying Southwest 737-800 aircraft to Hawaii for now.
Access the same great program
Flights to Hawaii on Southwest may help prices stay low among competing airlines, but there are additional reasons to fly Southwest Airlines over other options.
Not only does this airline offer the same great loyalty program for its flights to Hawaii, but you also get two free checked bags per person. You can use points to book any seat on a Southwest aircraft provided one is available, and many of their fares allow for last-minute cancellations or flight changes. You can even have your funds or points refunded for use on another flight - a perk almost no other airline offers.
Southwest Airlines flights to Hawaii can also be downright cheap, although pricing depends on where you fly out of. Initial launch prices went as low as $49 one-way on many of the routes, but that didn't last long. Now you're more likely to find one-way fares on routes like LAX-HNL and SAN-OGG for $198 (12,867 points) or more. That's still a great deal whether you pay in cash or points.
Southwest Companion Pass still applies
If you took advantage of this year's winter Southwest Companion Pass deal - or if you earned the pass the traditional way - you'll also be happy to know you can use this benefit to fly to Hawaii with the airline. The Southwest Companion Pass lets a designated companion of your choosing fly free with you whether you pay for your flight in cash or miles.
Read more: Southwest Airlines is running an unprecedented deal on its Companion Pass - here's how to earn and use it
To earn this pass, you need to fly 100 eligible one-way flights with the airline or earn 110,000 Southwest Rapid Rewards points within a calendar year. The easiest way involves signing up for personal and business credit cards from Southwest to score big sign-up bonuses. You can also focus on maximizing your Southwest earnings to meet the threshold through regular credit card spending.
More ways to earn Southwest Rapid Rewards
If you're angling to get to Hawaii this year but need more points to make it happen, don't forget just how many ways there are to score rewards with this airline. Not only can you earn points for paid fares with Southwest, but you can earn points with Southwest Rapid Rewards Dining or by clicking through the Southwest portal before you shop online.
If you need even more points to spend, also remember that Southwest Airlines is a partner of Chase Ultimate Rewards. This means that you can earn points with a card like the Chase Sapphire Preferred or Chase Sapphire Reserve and transfer them to Southwest Airlines at a 1:1 ratio.
But it also means you can maximize the Southwest Rapid Rewards program by earning signup bonuses on as many Chase Ultimate Rewards credit cards as you can, referring friends to Chase cards you carry, and using the Chase Ultimate Rewards portal when you shop online with participating stores.
The bottom line
If you want 2019 to be the year you finally get to Hawaii, Southwest Airlines wants to help your dreams come true. It offers affordable fares, two free checked bags per person, and a dynamic rewards program that comes with no blackout dates or capacity controls.
Because there are so many credit cards that let you earn Southwest Rapid Rewards points or transfer flexible points to the program, racking up enough points for a dream trip to Hawaii is easier than ever.
Disclosure: This post is brought to you by the Personal Finance Insider team. We occasionally highlight financial products and services that can help you make smarter decisions with your money. We do not give investment advice or encourage you to adopt a certain investment strategy. What you decide to do with your money is up to you. If you take action based on one of our recommendations, we get a small share of the revenue from our commerce partners. This does not influence whether we feature a financial product or service. We operate independently from our advertising sales team.
Business Insider may receive a commission from The Points Guy Affiliate Network, but our reporting and recommendations are always independent and objective.
Next Story
I'm an interior designer. Here are 10 things in your living room you should get rid of.
Higher-paid employees looking for work are having a tough time, and it could be a sign of a shift in the workplace 
A software engineer shares the résumé he's used since college that got him a $500,000 job at Meta — plus offers at TikTok and LinkedIn
7 scenic Indian villages perfect for May escapes
Paneer snacks you can prepare in 30 minutes
Markets crash: Investors' wealth erodes by ₹2.25 lakh crore
Stay healthy and hydrated: 10 immunity-boosting fruit-based lemonades
Here’s what you can do to recover after eating oily food
