Planning to Connect on Southwest to Hawaii? Here’s What You Need to Know

First, the good news. Southwest is selling tickets to Hawaii! Now, the bad news. It appears that it’s not such a scorching deal for anyone who needs to make a connection from a city east of the Pacific Time Zone.
While we’re seeing one-way fares as low as $49 (or 1,950 points) from many of Southwest’s West Coast gateways, availability and pricing seem volatile at best for those requiring a connection or two. Southwest plans to eventually fly from four California cities: Oakland (OAK), San Diego (SAN), San Jose (SJC) and Sacramento (SMF) to Honolulu International Airport (HNL), Lihue Airport (LIH), Kona International Airport (KOA) and Kahului Airport (OGG). But it isn’t launching all of those routes at once. Intra-island flights within Hawaii will also come later.
Southwest Airlines crew celebrate their inaugural flight to Hawaii at the Honolulu International Airport, Tuesday, Feb. 5, 2019, in Honolulu. (Photo by Marco Garcia / The Points Guy)
We’ve pushed Southwest’s booking portal to its limits by testing out fare possibilities from a variety of cities to give you an idea of what to expect if you’re hoping to Feel The Aloha LUV while originating from states like Missouri, Colorado, Georgia and New York — basically, anywhere not named California.

In This Post

East Coast
In testing Southwest’s booking engine with East Coast cities, we’re seeing a mixed bag of results in terms of what’s bookable and when. To boot, this seems to be rapidly changing.

Within an hour, availability and pricing on the airline’s Low Fare Calendar was markedly altered when looking at trips between Raleigh-Durham (RDU) and its three destinations in Hawaii.

Another oddity is New York City. While flights to Hawaii originating from LaGuardia (LGA) show no availability from now through the end of the booking window (currently pegged to Oct. 1, 2019), solid availability was found from Newark (EWR).

Perhaps unsurprisingly, Southwest is showing the most availability from its hubs, including Baltimore/Washington International Thurgood Marshall Airport (BWI).

Cities such as Atlanta (ATL) and Orlando (MCO) had plenty of available options, while the likes of Philadelphia (PHL), Boston (BOS) and Portland (PWM) showed practically no dates available for booking.

We’ve also found that even in months with ample options from East Coast cities, such as a full calendar between Raleigh-Durham and Maui in August, there’s no availability for a return. While you can purchase tickets nearly every day in August from North Carolina’s capital to Kahului (OGG), you cannot yet book a return on any day.
For now, it appears that East Coast dwellers are better off hanging tight with Southwest’s entrance into the 808. Fares aren’t spectacular, and we can’t say for sure that all connection options are loaded just yet.
Midwest and Central US
In the Midwest and central US, research suggests that bookable flights to Hawaii primarily show up for cities that currently fly direct between Oakland (OAK). For instance, flights operate nonstop between Austin (AUS) and Oakland (OAK), so Austin to Maui by way of an Oakland stop is available on a number of dates. However, those flights aren’t available every single day.

Once again looking at Austin as an example, the Southwest weekly flight schedule shows that AUS-OGG flights are only available Wednesday through Sunday for the week of April 7-13, and Sunday through Friday the following week of April 14-20.

Given that you can only fly Southwest between Minneapolis-St. Paul (MSP) and Honolulu (HNL) a single day in August, we’re left to surmise that the airline is still populating its booking engine. We expect these results to change quickly.

Departing from Indianapolis is totally doable in July, but beware of the Hotel California vibe waiting on the other end.

Southwest has yet to publish any one-way return flights from Honolulu back to the Hoosier State (and most other states, for that matter). This is most likely due to the lack of scheduled redeyes, as Southwest doesn’t want to sell itineraries that force you to sleep in an airport or get an overnight hotel before continuing on. Then again, there are worse places to be trapped than Oahu.

There are entire states that seem to be all but ignored. Southwest has yet to load a single route between Cleveland (CLE) and Maui/Honolulu.

Two hours down I-71, Columbus (CMH) is devoid of options until September.

Given Southwest’s presence at Chicago, it’s not a surprise to see ample flights out of Midway Airport (MDW).

In fact, Chicago is one of the few cities where Southwest has published fares for a return flight back to the mainland. (Though, the prices are far from attractive when looking at a points redemption.)
Western US
Generally speaking, the closer you get to California, the more likely you are to see wide availability of Southwest flights to Hawaii.

Available dates are far easier to find when originating in the western US through cities such as Boise (BOI), Phoenix (PHX), Denver (DEN) and Portland (PDX).

Phoenix (PHX) has far more daily flights between Oakland, which is accordingly reflected in the weekly schedule for an example week in mid-April. You’ll see that, while there are a number of flights that depart Phoenix at various times throughout the day, all of them funnel into the two daily flights between Oakland and Maui for those dates: Flight 3143 which arrives in OGG at 11:05am, or Flight 1466, which arrives in OGG at 8:00pm.

For example, you can fly between Portland (PDX) and Honolulu (HNL) every single day in August.

You’ll even have your pick of connection options, including a route through Oakland as well as San Jose.

Erratic behavior is still found, even from western cities. Departing from Albuquerque (ABQ), you’re able to book a seat to Honolulu practically every single day in September.

In July, however, you’re out of luck unless you’re game to pay sky-high rates to fly in on a Sunday.
International
Southwest now serves 14 international destinations, including locales in Mexico, Cuba, Belize and Costa Rica. We did our best to irk the airline’s booking portal by searching for fares between each of those outposts and Hawaii.

With a sole exception — Los Cabos (SJD) — Southwest has yet to enable ticket sales between its non-US cities and America’s 50th state. We suspect that will change in due time, but these routes will likely be enabled after US connections are ironed out.
Bottom Line
Maui’s Haleakala National Park is calling (Photo by Darren Murph / The Points Guy)
Considering that Southwest just began selling seats to The Aloha State, we aren’t surprised to see wonkiness when it comes to routes that require connections. Clearly, the airline’s California passenger base is in focus at launch, and we know there are plenty of flyers in San Diego as well as the Bay Area who will be quick to fill its first flights up.
Given the spotty availability and illogical pricing on many connecting routes, we’d advise patience. There appears to be no rhyme nor reason to what cities and dates are bookable, and frankly, pricing is higher than what we’re seeing on legacy US carriers. Our advice is to either snag a cheap Southwest ticket from its West Coast cities and book a positioning flight elsewhere using points and miles, or be quick on the trigger when legacy carriers begin to sell attack fares as we’ve seen with American Airlines.
To get prepared for when schedules are fully loaded and fares settle down, consider boosting your Southwest Rapid Rewards point balance with one of the credit cards below.

Southwest Rapid Rewards® Priority Credit Card ($149 annual fee) — This card is offering 40,000 bonus points after you spend $1,000 in purchases in the first 3 months. You’ll also get 7,500 bonus points after your cardmember anniversary, a $75 Southwest travel credit each year, 4 upgraded boardings per year (when available), 20% back on inflight drinks and Wi-Fi and 2 points per $1 spent on Southwest purchases and Rapid Rewards hotel and car rental partner purchases. You’ll earn 1 point per $1 spent on all other purchases, and there are no foreign transaction fees to sweat.
Southwest Rapid Rewards® Premier Credit Card ($99 annual fee) — This card is offering 40,000 bonus points after you spend $1,000 in purchases in the first 3 months. You’ll also get 3,000 bonus points after your cardmember anniversary. You’ll earn 2 points per $1 spent on Southwest purchases and Rapid Rewards hotel and car rental partner purchases. You’ll earn 1 point per $1 spent on all other purchases.
Southwest Rapid Rewards® Plus Credit Card ($69 annual fee) — This card is offering 40,000 bonus points after you spend $1,000 in purchases in the first 3 months. You’ll also get 3,000 bonus points after your cardmember anniversary. You’ll earn 2 points per $1 spent on Southwest purchases and Rapid Rewards hotel and car rental partner purchases. You’ll earn 1 point per $1 spent on all other purchases.

This article was updated to clarify that Southwest does not yet have scheduled redeyes returning from Hawaii, impacting connection options back to the mainland.
Additional reporting by Katherine Fan and Summer Hull; featured image courtesy of Marco Garcia / The Points Guy. 

How to Plan a Points and Miles Trip for a (Very) Large Family

The more a family grows, the more difficult it is to corral everyone at the same time in the same place. Sure, it can still happen at the usual events such as weddings and major holidays, but the likelihood of a large family vacation seems to shrink as the family expands.
But as my family proved last week, it isn’t impossible. Through many hours of planning over the course of many months, I was able to coordinate a trip for a family of 24 people (yes, you read that right) to Puerto Rico. The best part about it was that I flew everyone there, all two dozen of us, on points and miles.
Of course, I learned plenty along the way. So if you’re trying to arrange a large vacation that the entire family will be talking about for the rest of their lives, consider this your definitive guide.
The Biros Family Puerto Rico crew. All here on points.
How It Began
The catalyst for this massive family getaway was a pretty unusual scenario, and actually the same reason I ended up as a writer for TPG. I won TPG’s Marathon to a Million contest almost three years ago and landed the one million JetBlue TrueBlue points prize, novelty check and all.
However, even then (as I noted in my first-ever article for TPG explaining what I’d do with my winnings), I didn’t think planning a trip for my entire family was a possibility. But my dad, who had accumulated a few hundred thousand Amex Membership Rewards points through his small business, expressed an interest in doing “something” for the family with these points. He also pointed out that he had no idea how to do so.
As I became more skilled in the points and miles game, I realized I could actually make this happen between his points and mine. And I learned how surprisingly attainable a large family points and miles trip was, even without winning a big contest.
Step 1: Pick a Time and Place That Works for Everyone
This is really the only thing that everyone has to agree on, and it can prove to be difficult — perhaps the most difficult part of the planning process. For example, maybe a ski trip sounds fun to the majority of your family, but it’s tough to sell it to a family member that has no interest in skiing. For my family, I wanted a warm, tropical paradise, and I knew that would interest everyone. I also wanted a destination that wouldn’t require passports. Almost none of my nieces and nephews own a passport, and at $115 to $145 each, it’s a significant expense.
So I settled on Puerto Rico. It was easily accessible from the Midwest with options on JetBlue. And although no one would need passports, the language and culture would feel remote for someone who has never left the continental United States.
No one in the family was opposed to escaping the Midwest in January.
Another tip: Don’t dwell if someone can’t go or chooses not to. Chances are, if you’re reading this, travel is a high priority. But it’s not for everyone else. You and I may think it’s crazy to turn down a free family vacation, but other people have other priorities. Move on, and focus on making this the best trip for those who do see the value in it.
Step 2: Book Flights As Soon As They Go on Sale
When you are booking a large number of flights with points, it’s best to do so as soon as they go on sale. Refer to this guide to know when each airline releases their tickets, but low-cost carriers typically work the best. Unlike the big three airlines that release flight schedules 11 months in advance, low-fare carriers release schedules six to nine months out, meaning if you are booking flights as soon as they go on sale, you only need to plan that far in advance.
If the routing works, I recommend Southwest Airlines for the following reasons:

Generous Baggage Policy: Two free checked bags per person is especially important for inexperienced travelers who will likely overpack.
Schedule Release Dates: Southwest is usually the last major airline to release tickets, which means if you are booking flights right when they go on sale, you won’t have to plan as far in advance as the other airlines. This link will tell you when the next batch of flights will be released.
Ticket Prices on Release Date: Unlike airlines like JetBlue that horribly inflate ticket prices for holiday times even when a ticket for a flight has yet to be sold, Southwest appears to release all of their seats at the same low price regardless of dates. This is crucial if you’re trying to book a trip over the holidays, which may be the only time you can line up a group that includes school children.
Award Ticket Pricing: Unlike the big three, the number of points required to book a flight on Southwest is tied to the fare of the ticket. Therefore, you don’t have to worry about award inventory, and won’t end up paying double for a standard award if your family outnumbers the award seats available. If anything, the ticket price will increase by a few thousand points after you book up some of the seats.
Generous Cancellation and Change Policy: No other airline compares with Southwest’s cancellation policy on awards. If you cancel, the points are simply put back in your account. Changes are free, too. You’ll just pay the difference in points.
Family Boarding: If you have children in your group, your entire party could potentially board between groups A and B. Even on a full flight, you’ll be able to sit everyone together in open rows toward the back of the aircraft. Honestly, assigned seating would be easier, so family boarding isn’t necessarily better, but at last you know open seating won’t work against you. And it definitely beats airlines that want to charge for assigned or preferred seats.

On the outbound flight, we got 19 family members in three consecutive rows using Southwest family boarding.
Also, remember that the Companion Pass works on award bookings as well, and it’s currently available through this amazing Southwest credit card offer.
My initial plan was to get most flights on JetBlue, but the pre-inflated ticket prices over Christmas made that pretty much impossible. I was able to pivot our trip to New Years, and I snagged one semi-reasonable return fare for most of us in early January. For my sister’s family, I found a doable outbound fare from Indianapolis on Delta Air Lines that made use of my dad’s Amex points. But the bulk of our flights were booked on Southwest at a great fare as soon as they went on sale. If we had enough Southwest and Chase points, we would have booked everything on Southwest.
Between the three airlines we redeemed a total of 715,860 points for 46 flights (not including a lap baby). Here is the breakdown by airline:

Airline
Southwest
JetBlue
Delta

Number of Flights
25
16
5

Points Redeemed
328,380
289,980
97,500

Average Redemption
13,135
18,124
19,500

 
The numbers above include the 10% rebate on JetBlue redemptions I get with my JetBlue Plus Card, but I still got the best value on Southwest. And, in addition to the various reasons mentioned above, it was also the most convenient option, with a direct flight from Chicago Midway (MDW).
Step 3: Book a Huge Airbnb (or Two)
While there unfortunately isn’t a great way to redeem points for Airbnbs, it does provide the best value on several levels. Here are several reasons large rental houses booked through sites such as Airbnb and VRBO are better for large families than hotels:

Large Communal Living Spaces: This is what makes it a true family vacation. A large area where the family can all gather together, be it a living room or an outdoor pool area. This is where everyone can relax and when the real bonding occurs. This happens far less when families are compartmentalized in hotel rooms.
A Full Kitchen: Compared to eating out every meal, you’ll save quite a bit of money when you prepare large family meals at home together in a full kitchen. Plus, like I said before, it’s a great space for bonding.
Overall Cost Is Cheaper: When you add up the price to house everyone in hotel rooms, the per person cost is usually much cheaper in a house rental.
Privacy: Large rentals often have pools, yards or decks, and these are normally reserved for your family only. This is also much less stressful for parents of small children who can give their kids more freedom than they would in a public setting.

A large communal living space means more quality cousin time.
However, these large rental units are often not in huge supply, and the best value properties get booked up way in advance. So, like plane tickets, the sooner you reserve these the better.
I had to get two Airbnb rentals to house our entire family. While there were options that would fit all of us, I wasn’t in love with any of them. I decided to keep an eye on listings over the course of a couple months in hopes that a new listing would pop up that would work. With the rental market constantly changing, especially following Hurricane Maria, this was a good possibility.
Sure enough, a rental with a private pool located a block from the beach in San Juan eventually appeared. It was a beautiful and newly renovated six bedroom, five bath home for $600 per night for 15 people. I then found a top floor apartment with private roof access and beautiful views of Isla Verde beach to house the other nine of us for $350 per night, just 50 feet from the main house.
The view of Isla Verde beach from the private rooftop of our second Airbnb.
Step 4: Get Others Involved in Planning
While you may be the most qualified to handle the flight bookings, others will inevitably want to chip in and help out. They can peruse Airbnb and VRBO listings as well. Or you can suggest they look up ideas for activities on the ground.
Getting the entire family to participate in elements of trip planning can help every member of the group feel more involved and excited. I told my family to check TripAdvisor and to pick up guide books from their library. Even the kids can help with this.
My sister branched off and took her family with older grandkids to El Yunque National Forest for a day.
Step 5: Look Into Charter Tours
There are a few luxuries that become accessible for a reasonable rate (per person) that you simply couldn’t get with a smaller group. One, as I already mentioned, is a lavish Airbnb. Another is the option to do private or charter tours. If you find a tour that has a capacity at or slightly above your group size, the per person cost is likely less than if you were paying individually for a spot. And you’ll get a private tour for your group, which you can likely customize as needed.
Snorkeling during our chartered boat trip was the highlight for many of the kids.
For our group of 24 people, we booked the 25 person capacity Innovation boat through Kayaking Puerto Rico. While I rarely do tours, this organized experience proved to be great for our group. The guides taught the young ones how to snorkel and guided them through the reef. And the price per person was about 10% cheaper than if we had all paid individually.
Step 6: Roll With the Changes
Just like any vacation, not everything will go according to plan. However, that’s much more likely to happen with a massive group. Roll with it and adjust when necessary. This trip was originally scheduled and completely booked for Thanksgiving of 2017. However, Hurricane Maria cancelled those plans. I was able to get everything refunded and book it again for the New Year of 2019, and it was much easier the second time around.
Step 7: Treat It Like a Once in a Lifetime Trip
As this is probably the first time you’ve done a trip of this magnitude, make the most of every moment and interaction. Encourage more campfire and sunset beach time than TV time. In fact, you may even want to consider a TV-watching restriction. Perhaps the experience will show you and everyone else involved that massive family vacations are possible, and you’ll all  decide you want to do it again. But there’s also a very real chance that this is a once-in-a-lifetime trip. So be sure to treat it like one.
My family members had plenty of their own advice, too, which I recorded in this Instagram story takeover.
The whole gang at the Castillo San Felipe in Old San Juan.
The Bottom Line
What I learned above all else is how possible a points and miles trip of this size actually is.
I expected the trip to use most of my TrueBlue points and my dad’s accumulation of Membership Rewards points. But in reality, my dad’s Chase Ultimate Rewards points and Southwest Rapid Rewards points paid for the bulk of the flights, and he only started earning those points three years ago when I taught him how to attain the Companion Pass using Southwest credit cards. (I also had him to shift his personal expenses to the Chase Sapphire Reserve and business expenses to the Chase Ink Business Preferred credit card, earning Ultimate Rewards points that could be transferred to Southwest, his airline of choice.)
This vacation could very possibly be done again if I coached the rest of my family on points as I did my parents. But, as my mom stated on the flight home, “Let’s wait a few years.”
So long from the Biros family in Puerto Rico. All 24 of us.
I hope our family vacation tale has inspired you to do the same with your family, or even a large group of close friends. Feel free to reach out with any other questions that could help make this trip more attainable for you.
The Points & Miles Backpacker is a weekly column appearing every Monday. TPG Contributor Brian Biros, who has backpacked the globe for the past 15 years, discusses how to fund this adventurous, budgeted and increasingly popular form of travel with points and miles. He’ll also explore all things backpacking-related. Read his story here and high-level approach here. He’s taking a break from his normal column this week to share his family time.
All images courtesy of the author.