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Why I ONLY Fly Southwest to Hawaii + How to Find YOUR Best Airline Options

I get a lot of questions about what the “best” airline is to fly to Hawaii.

My answer is always…it depends. Mostly on where you’re flying from. Different airlines have different hubs and routes which make them more attractive than other airlines when flying out of certain cities. 

As far as the best airline from an experience point of view, I hate to break it to you, but air travel isn’t glamorous these days. Unless you’re flying first class (on a nice plane), economy travel from the mainland to Hawaii is mostly about…just getting there. No one has good food, no one has a luxury experience.

Best Airlines to Fly to Hawaii

That being said, if you’re a frequent traveler (or trying to figure out how to be one), you’ll get the most perks and bang for your buck by picking one airline and sticking to it. 

When I’m looking at flight options to Hawaii, I’m always thinking about 1) how to use points to get there or 2) if I’m paying cash who to pick so I’ll earn points to use next time. 

That’s why I fly Southwest 100% of the time I go to Hawaii. 

I’ll tell you all about why (+ how to get free flights) plus give you the rundown on when it might make sense for YOU to fly on another airline (I’ll cover all the big ones that fly to Hawaii…American, United, Delta, Hawaiian, Alaska). 

This post may contain some affiliate links, which means I’ll make a little money on anything you choose to purchase. But of course, I only recommend my absolute favorites to you. Thank you for supporting the brands that make HulaLand possible.

Why I ONLY Fly Southwest Airlines

So, some general reasons why I prefer to fly Southwest:

Prices usually are cheaper than major airlines (not like half price – unless they’re running a crazy sale – cheaper is still cheaper). 

Bags are FREE. You get two free checked bags per person. That’s more mai tai money once you get to Hawaii!

They manage their layover situation really well. I think American Airlines plays a game to see how far they can have you running across a major airport during a 50 minute layover. Southwest scheduling always has connecting flights really close to each other. WAY better chances of making those connections. 

I’d rather pick my seat the day of then when I book. It levels the playing field. When you’re booking in advance, you have NO IDEA who’s going to be sitting next to you. When it’s first come first serve, you can scope out the situation as you board the plane and choose what’s going to work best for you. Also, most major airlines now make you pay more money to book a “premium” seat in advance. With Southwest, set an alarm so you don’t forget to check in exactly 24 hours in advance and you’ll have plenty of options when you board the plane. 

Their cancellation and modification policies are super reasonable. They never make you pay a fee to change your flight (you just pay the difference if the new flight is more than the old one or they refund you the difference if it’s cheaper). And if you cancel, they give you an automatic credit (plus they have a booking category that is fully refundable). 

And on a personal note…Southwest is my best option because I don’t live in a city with direct flights to Hawaii. I fly out of Tulsa, OK so options are LIMITED and I’m guaranteed to have to make a connection somewhere else. If I had direct flight options on another major airline, I wouldn’t choose to fly Southwest (with a connection) over an airline with a direct flight. 

Flying Southwest Airlines to Hawaii

Here’s what Southwest flights to Hawaii look like.

You can fly direct to Hawaii on Southwest from: 

Las Vegas (LAS) to Maui (OGG), Oahu (HNL), Kauai (LIH), Big Island (KOA)

Oakland (OAK) to Maui (OGG), Oahu (HNL), Kauai (LIH), Big Island (KOA)

Phoenix (PHX) to Maui (OGG) and Oahu (HNL)

Sacramento (SMF) to Oahu (HNL)

San Jose (SJC) to Oahu (HNL)

Los Angeles (LAX) to Oahu (HNL)

Long Beach (LGB) to Oahu (HNL)

San Diego (SAN) to Oahu (HNL)

If you live in one of those cities, you are GOLDEN. You’ll be able to find flights fairly cheap (and low miles) and it’s an easy 4-6 hour flight. 

If you do not live in one of those cities (hi, it’s me), you’ll need to do a little research into which (if any) you can fly directly from your city to. 

For example, flying from Tulsa, OK, I can get direct flights on Southwest daily to Las Vegas and Phoenix, making those options for me to get to Hawaii (Southwest won’t sell you a through ticket with more than one connection). 

Now, the flight times have to line up so you’ll be able to do it all in one day, but I can usually make something work even if it’s just on certain days of the week. 

Maybe you noticed that from Las Vegas you can fly to all four of the main Hawaiian Islands, and that’s not by accident. 

First of all, Las Vegas is a wildly popular destination with Hawaiians so there’s always demand for those flights. 

Second, most mid-sized cities in the US have direct flights to Las Vegas making it the perfect “hub” for Southwest to use for people who don’t live in one of the cities with a direct flight and need to make a connection. 

Live in Minneapolis, Dallas, Denver, Memphis, Albuquerque, Charlotte, Chicago, Columbus, Pittsburgh, etc? You can probably get a direct flight to Vegas which opens up Hawaii to you. 

So flying to Hawaii from Las Vegas, Oakland, Phoenix, Sacramento, San Jose, Los Angeles, Long Beach, or San Diego will generally be fewer points (and a cheaper cash price) than if you have to make a connection, but you’ve got options. And that’s not even taking into account a sale.

PLUS…when Southwest entered the Hawaii market, they also added a TON of interisland flights so even if you can only get to Oahu from the mainland, you can easily island hop once you get there. 

Side Note: If you’re looking for a rental car for your trip, I LOVE Discount Hawaii Car Rentals. They’re seriously the only company I ever use. They’ll give you the very best prices, you don’t have to reserve with a credit card or pay until you show up, you can cancel and re-book anytime if you find a better rate, and they usually have a special that adds additional drivers for no fee. It’s a no brainer. Click here to check rates for your trip.

How I Get Free Flights on Southwest

I think Southwest is the most straightforward airline to book using points. The point values for flights directly correspond to the cash price. And they don’t throttle the availability of point redemptions. If there’s a seat available on that plane, they’ll let you book it for cash or for points. 

A lot of bigger airlines only reserve so much capacity on each flight for point redemptions so if you don’t book immediately when the booking window opens, you can’t use your points even if you have them to burn.

Okay, so…how to get free flights? 

I have this Southwest Premier Rapid Rewards Visa card through Chase. The current sign up offer is 50,000 points. Depending on where you live and fly from, that’s at least one completely FREE ticket to Hawaii and it could be two depending on the time of year (or more if you catch a crazy sale). 

The card also gives you:

2 Early Bird Check-Ins per year (super nice when you’re going to Hawaii and the perfect seat is really important)

6000 anniversary points

3x points on Southwest purchases (more points for your next flight)

If you’re new to the “travel hacking” game, I think this is a REALLY good place to start. You’ll get some free flights right away and honestly, I feel like Southwest points rack up sooooo fast when you’re using the card for your everyday purchases. 

Again, use >>this link<< to get 50K bonus points when you sign up. 

But my FAVORITE Southwest points feature is the Companion Pass. If you rack up enough points in a calendar year (through credit card spending and flights flown), you get a Companion Pass. For the entire year, every time you fly, you get to take somebody with you FOR FREE (whether you pay cash or book with points). 

The Companion Pass is good for the rest of the year when you qualify plus the entire next year (for example: if you qualify in October, you get the Companion Pass for the rest of that year plus the entire next year)

So once you qualify for a Companion Pass, your points actually end up going twice as far. 

It’s too good to pass up. Details >> here <<

Other Airlines That Fly to Hawaii

Besides Southwest…American, United, Delta, Hawaiian, and Alaska all fly to Hawaii. Here’s a quick rundown of where each flies out of so you’ll know if one is a good option for you: 

United Airlines

If you’re flying out of any of these cities, United is a great option for Hawaii:

Chicago (ORD) has flights to Oahu (HNL), Kona-Big Island (KOA), and Maui (OGG)

Denver (DEN) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG)

Houston (IAH) has flights to Oahu (HNL)

Los Angeles (LAX) has flights to Oahu (HNL), Hilo-Big Island (ITO), Kona-Big Island (KOA), Kauai (LIH), and Maui (OGG)

New York Newark (EWR) has flights to Oahu (HNL) and Maui (OGG)

Orange County (SNA) has flights to Oahu (HNL)

San Francisco (SFO) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG)

Washington Dulles (IAD) has flights to Oahu (HNL)

I’m currently working on the United Explorer MileagePlus (Chase) sign up bonus for an upcoming trip to Tokyo, but one of the things I’m most excited about is that if you book a cash ticket with United, you can use your miles to upgrade your economy seat to business class. 

I don’t think that’s a big deal if you’re flying to Hawaii from the west coast, but if you’re flying from the east coast (even Houston or Chicago) it’s sooooo much nicer to fly in business or first class. 

If you use >>this link<< to sign up for the card, you’ll get a 50K point bonus which could be enough to book a free economy ticket to Hawaii OR upgrade your economy ticket to first class. 

The other reason I love this card is because United is one of Chase’s travel partners and my Chase Sapphire Reserve card is my go to travel card in general. So I can transfer my Chase Ultimate Rewards points to United to book directly if there’s a flight that works best for me. 

And United is also in a bigger airline alliance so you have a lot of options to use your points on other airlines if you travel internationally. 

Grab that United 50K bonus here

American Airlines

If you’re flying out of any of these cities, American Airlines could be a good option for Hawaii:

Dallas (DFW) has flights to Maui (OGG) and Oahu (HNL). These two routes are AA’s “Flagship” Hawaii routes meaning they fly a widebody aircraft more commonly seen on international flights. You’ll get a full meal plus the option for premium economy seating and lie flat seats in business class. These flights are usually more $$$ even in economy. 

The rest of these routes are just standard domestic flights: 

Los Angeles (LAX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).

Phoenix (PHX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).

*AA used to fly some routes to Hawaii from Chicago and Charlotte, but those aren’t currently offered. 

Delta Airlines

If you’re flying out of any of these cities, Delta could be a good option for Hawaii:

Atlanta (ATL) has flights to Oahu (HNL) and Maui (OGG).

Detroit (DTW) has flights to Oahu (HNL).

Los Angeles (LAX) has flights to Oahu (HNL), Kauai (LIH), Kona-Big Island (KOA), and Maui (OGG).

Minneapolis (MSP) has flights to Oahu (HNL).

New York (EWR) has flights to Oahu (HNL).

Salt Lake City (SLC) has flights to Oahu (HNL).

Seattle (SEA) has flights to Oahu (HNL).

Delta also offers interisland flights so you can connect to another island through Honolulu. 

Hawaiian Airlines

If you’re flying out of any of these cities, Hawaiian Airlines could be a GREAT option for Hawaii (get those aloha vibes going before you even get there ; )

Austin (AUS) 

Boston (BOS) 

Las Vegas (LAS) 

Long Beach (LGB)

Los Angeles (LAX)

New York (JFK) 

Oakland (OAK)

Ontario, California (ONT)

Phoenix (PHX)

Portland (PDX)

Sacramento (SMF)

Salt Lake City (SLC)

San Diego (SAN)

San Francisco (SFO)

San Jose (SJC)

Seattle (SEA)

Hawaiian Airlines also offers an extensive network of interisland flights. 

Alaska Airlines

This west coast based budget carrier isn’t something that’s ever on my radar (since I fly from the middle of the country), but if you’re flying out of one of these cities, they’re usually very competitively priced. 

Anchorage, Alaska (ANC)

Portland (PDX)

Los Angeles (LAX)

San Diego (SAN)

Seattle (SEA)

San Francisco (SFO)

San Jose (SJC)

Always Book Directly with the Airline

Whichever airline you choose, be sure to follow the cardinal rule of air travel. ALWAYS BOOK DIRECT. Under no circumstances should you ever book airfare through a third party company like Expedia, Travelocity, and I hate to say it but even Costco. Air travel is WILD. Wildly undependable.

Flights get delayed, they get canceled, plans get derailed. And when you’ve booked through a third party, you can’t deal with the airline directly. You can literally be in the airport at the gate and depending on what the problem is (flight canceled, flight delayed and you’re going to miss your connection, etc) the gate agent may not be able to help you. 

You haven’t known frustration until you’re literally standing in front of a human that handles flight changes for the airline and they can’t help you because you have to call Expedia and be on hold with them for 6 hours instead. When you book with a third party, THEY hold the reservation, not you. 

Here’s the other thing…these booking sites hardly ever have prices any cheaper than the actual airline anyways. Do your research using Expedia or whoever you like to shop and then go directly to the airline to book.

Here’s one more really important thing you need to know before your Hawaii trip…

Reservations You Need to Make BEFORE Your Hawaii Trip

You’ve got your airfare, hotel, rental car and your big activities booked, so you should be good to go, right? Wrong!

Travel is BOOMING in Hawaii so a lot of state and national parks used the closure and reopening to institute reservation systems at some of the island’s most popular spots to make things a little more sustainable.

That means that there are now over half a dozen sites (beaches, trailheads, etc.) that require advance reservations. And some sell out well before you arrive on the island so you really need to have some sort of a plan.

I recently saw somebody in a Hawaii travel group post in a panic that they didn’t know they had to make reservations for things in advance…they thought they could just show up and “go with the flow.” I was tempted to say, well, “as long as the flow doesn’t take you somewhere that requires reservations, you can!” ; )

But I don’t want YOU to be that person, so I’ve pulled together a list of all the places you need to reserve entry in advance (plus all the details on booking windows, price, links, etc.) and a handful of popular tourist hotspots that book out really far in advance too.

Haleakala National Park (Maui)

To visit Haleakala National Park for sunrise at the summit, you must make reservations in advance here.

Reservations are required to enter the park gates between 3AM and 7AM (sunrise hours).

Online reservations are $1 per reservation/vehicle PLUS you’ll pay the park entrance fee of $30/vehicle when you arrive (National Park annual passes are also accepted at the gate).

The reservation booking window opens 60 days in advance at 7AM HST. There are also a limited number of tickets released two days before.

You can make one reservation every three days with the same account. So if you want to make reservations for back to back days (in case of weather/conditions), you’ll need to do so with separate accounts (email addresses).

If you can’t get reservations for sunrise, you can enter the park anytime after 7AM without reservations. The summit is spectacular during the day and you don’t need reservations for sunset.

I strongly recommend creating an account before and making sure you’re logged in at 7AM HST because it’s not uncommon for reservations to sell out quickly.

Waianapanapa State Park (Maui)

To visit Maui’s famous black sand beach at Waianapanapa State Park on the Road to Hana, you must make reservations in advance here.

Reservations are required to visit the beach and are distributed in windows from 7AM-10AM, 10AM-12:30PM, 12:30PM-3PM, and 3PM-6PM. And they are pretty strict about exiting by the end of your window time (you can arrive anytime within your window).

It’s $5/person to enter plus $10/vehicle to park and those fees are paid when you book your time slot.

Reservations open up 30 days in advance.

Iao Valley State Park (Maui)

To visit the lush, green mountains and hike at Iao Valley State Park, you must make reservations in advance here.

Reservations are offered for 90 minute time slots beginning at 7AM and ending at 6PM. They ask that you arrive within the first 30 minutes of your time slot.

Entry is $5/person plus $10/vehicle to park.

Reservations open up 30 days in advance.

Diamond Head (Oahu)

To hike to the top of Waikiki’s famous Diamond Head, you must make reservations in advance here.

Reservations are offered in two hour increments beginning at 6AM (6AM-8AM, 8AM-10AM, etc.) and ending at 6PM. If you’re parking onsite, they ask that you arrive within the first 30 minutes of your reservation window.

Entry is $5/person plus $10/vehicle to park.

Reservations open up 30 days in advance.

Tip: I recommend booking one of the first two time slots because there isn’t much shade on this hike and it gets pretty hot.

Hanauma Bay (Oahu)

To snorkel at Oahu’s pristine Hanauma Bay, you must make reservations in advance here.

Entry times are staggered in 10 minute increments from 7AM to 1:20PM with roughly 1000 slots being assigned in advance every day.

Reservations can be made two days in advance and they open at 7AM HST. They’re usually gone in minutes (if not seconds).

If you’re unable to get an advanced reservation, you can try for a day of, walk in ticket. They open at 6:45AM and they only have a limited number available. Everyone in your group needs to be present when you purchase your tickets in person.

There are no reservations for parking and it’s first come, first serve. $3/vehicle.

It’s $25/person to snorkel at Hanauma Bay (12 and under, active military, and locals with HI ID are free).

The Hanauma Bay Nature Preserve is open Wednesday through Sunday (CLOSED MONDAY AND TUESDAY) from 6:45AM-4PM. Last entry is at 1:30PM, the beach is cleared at 3:15PM and you have to leave the facility by 4PM.

Jellyfish patterns can also affect whether or not the bay is open so double check the day before/day of.

USS Arizona at Pearl Harbor (Oahu)

If you want to take the boat tour at Pearl Harbor out to the USS Arizona, it’s recommended to make advance reservations here.

Online reservations are guaranteed a specific boarding time to go out to the USS Arizona. If you’re unable to get an advance reservation, you can wait standby when you arrive. The line could be short (15 minutes or so) or long (hours) and it just depends on the day (if they’re having problems with the loading dock sometimes they don’t take many from the standby line) and the time of day.

Reservations are supposed to open up 60 days in advance, but keep an eye on your exact dates, because lately they’ve actually been opening up about 57ish days in advance???

They also release a small batch of tickets the day before.

The boat ride out to the USS Arizona is free, but it’s $1 to make the reservations online.

They recently started charging $7/vehicle for parking at Pearl Harbor.

Haena State Park / Kalalau Trail (Kauai)

If you want to hike Kauai’s famous Kalalau Trail, you must make advance reservations here.
You’ve got three options here:

1) Parking & Entry: This is the most flexible option and also the most limited. THESE RESERVATIONS SELL OUT IN LESS THAN A MINUTE. There are three time slots available: 6:30AM-12:30PM, 12:30PM-5:30PM and 4:30PM to sunset. You can purchase multiple time slots if you want to stay longer. It’s $10/timeslot (parking) plus $5/person and you have to reserve every person when you initially book. Everybody has to arrive in the same car and your ID needs to match the reservation.

2) Shuttle & Entry: If you can’t get parking at the trailhead, there’s also a shuttle option. Shuttle reservations are $35/person (16+), $25/person (ages 4-15), 3 and under can ride free. The shuttle runs every 20 minutes 6:20AM to 6:40PM.

3) Entry Only: If you’re a Hawaiian resident (with HI ID) or someone WITH a Hawaiian resident, you can purchase entry only for $5/person with no advance reservations. Also, if you’re walking or biking to the trailhead you can do this option. But there is NOWHERE to park in the area to walk in. So this really only works for those with bikes or who are staying close enough to walk. They will tow your car if you park outside the designated areas.

The reservation window opens 30 days in advance at 12AM HST. The parking & entry option usually sells out in a minute, but the shuttle availability will last longer.

There are a TON of FAQs here including the possibility of snagging a canceled reservation.

Other Things to Book in Advance

Hawaii is a busy place these days! Besides the state and national parks above, here’s a handful of miscellaneous things you should make reservations for in advance (if they’re on your radar):

Mama’s Fish House (Maui): The iconic spot is the most popular restaurant in Hawaii and dinner reservations usually start filling up about 6 months in advance (they open up bookings 18 months in advance). Make reservations through their website and if the dates you want are already booked, you can join a waitlist. Most people have pretty good success getting in on the waitlist (even if it’s for lunch).

Old Lahaina Luau (Maui): Honestly, any luau you’re planning to attend you should book early, but most people are usually shocked how far out the Old Lahaina Luau books out. Book it as soon as you know your dates (I think they open at the six month window). They also have a waitlist.

Kualoa Ranch UTV Tour (Oahu): Everybody loves Jurassic Park so getting to ride UTVs where they filmed the movies is very popular. The ranch offers a lot of different tours but the UTV tours usually book out a couple of months in advance.

Spa Reservations: If you’re staying at a resort with a spa (or planning on visiting one), don’t wait until you arrive to make your reservations. I’d make them at least a month in advance.

Tee Times: Same for golf, reserve your tee times well in advance.

Dining Reservations: Any “fancy” or resort restaurant is likely to be booked up these days so if you like having a nice dinner every night, make your plans in advance.