$119 Find Cheap Flights to Wailea

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Wailea departing on 5/13. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flight Deals to Wailea

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Wailea that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals to Wailea

KAYAK's recommended round-trip deals from the most popular airlines that fly to Wailea.
Discover the best prices for you by selecting your travel dates on KAYAK.
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Alaska Airlines Logo
4:27 pm - 7:35 pmSAN-OGG
6h 08mnonstop
Alaska Airlines Logo
11:13 pm - 7:35 amOGG-SAN
5h 22mnonstop
$238Alaska Airlines
Find Deal
Tue, May 13 - Thu, May 22
Hawaiian Airlines Logo
6:32 pm - 9:34 pmSAN-OGG
6h 02mnonstop
Hawaiian Airlines Logo
11:13 pm - 7:35 amOGG-SAN
5h 22mnonstop
$242Hawaiian Airlines
Find Deal
Thu, Jun 5 - Thu, Jun 5
Hawaiian Airlines Logo
4:27 pm - 7:35 pmSAN-OGG
6h 08mnonstop
Hawaiian Airlines Logo
12:45 pm - 11:58 pmOGG-SAN
8h 13m1 stop
$243Hawaiian Airlines
Find Deal
Tue, May 6 - Tue, May 13
Alaska Airlines Logo
4:27 pm - 7:35 pmSAN-OGG
6h 08mnonstop
Alaska Airlines Logo
10:35 am - 11:38 pmOGG-SAN
10h 03m1 stop
$248Alaska Airlines
Find Deal
Tue, May 13 - Wed, May 21
Delta Logo
7:00 am - 4:50 pmSAN-OGG
12h 50m1 stop
Delta Logo
9:10 pm - 12:38 pmOGG-SAN
12h 28m1 stop
$257Delta
Find Deal
Wed, Sep 3 - Mon, Sep 8
American Airlines Logo
10:04 am - 1:43 pmPHX-OGG
6h 39mnonstop
American Airlines Logo
11:23 pm - 8:05 amOGG-PHX
5h 42mnonstop
$264American Airlines
Find Deal
Thu, Sep 25 - Wed, Oct 1
American Airlines Logo
1:25 pm - 7:24 pmPDX-OGG
8h 59m1 stop
American Airlines Logo
10:00 pm - 12:45 pmOGG-PDX
11h 45m1 stop
$277American Airlines
Find Deal
Tue, Aug 26 - Tue, Sep 2
Delta Logo
7:20 am - 5:01 pmSAN-OGG
12h 41m1 stop
Delta Logo
9:30 pm - 2:22 pmOGG-SAN
13h 52m1 stop
$277Delta
Find Deal
Mon, May 12 - Tue, May 20
United Airlines Logo
9:05 am - 11:45 amSFO-OGG
5h 40mnonstop
United Airlines Logo
10:30 pm - 6:37 amOGG-SFO
5h 07mnonstop
$278United Airlines
Find Deal
Fri, May 9 - Tue, May 13
United Airlines Logo
6:00 am - 11:56 amPHX-OGG
8h 56m1 stop
United Airlines Logo
10:30 pm - 12:26 pmOGG-PHX
10h 56m2 stops
$288United Airlines
Find Deal
Wed, May 7 - Wed, May 14

Good to know - Book Cheap Wailea Plane Tickets

Low season

January

High season

July

Cheapest flight

$119
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from San Diego to Kahului

Flights to Wailea: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Wailea 
Verified travelerFlew with Hawaiian AirlinesLGB-OGGApr 2025
Long Beach airport is great. Quick and easy entry and exit.
Verified travelerFlew with Hawaiian AirlinesLAX-OGGJan 2025
a must, you need a to car to get around there is a lot to see. There’s a lot of good food plus try the shave ice cone. I haven’t seen any bad vibes the people here mind their own business. The food can be pricey at Maui so be ready and save.
KimberleyFlew with Alaska AirlinesSEA-OGGNov 2024
Pack snacks and patience. Ear plugs or noise-cancelling headphones are a must!
Verified travelerFlew with Alaska AirlinesSAN-OGGOct 2024
Try a different airline. They may be a bit more honest.
ChuckFlew with Hawaiian AirlinesHNL-OGGOct 2024
Take another airline that trains their flight attendants not to be cold and hostile.
Verified travelerFlew with Hawaiian AirlinesLAX-OGGJul 2024
New flight was on southwest, not direct, one layover, but service was top notch. Excellent considering conditions it was booked under
Verified travelerFlew with Hawaiian AirlinesLGB-OGGAug 2024
Long Beach is a great airport and I would gladly fly out of there than LAX
Verified travelerFlew with Alaska AirlinesSEA-OGGMay 2024
This was my first ever flight, I have no view points on other flights. I really enjoyed the flights.
RobertFlew with Hawaiian AirlinesLAX-OGGMay 2024
Hawaiian Airlines is the best. With food service , good entertainment and great customer service. Can’t go wrong.
BryanFlew with Alaska AirlinesSAN-OGGMay 2024
Airlines are becoming much stricter in limiting people to one carry-on bag and one personal item.
LaurenFlew with Hawaiian AirlinesLAX-OGGFeb 2024
If you’re flying on the 8am flight, they serve a yummy breakfast sandwich. Maybe skip breakfast in the airport. Oh and you can buy top ramen onboard too, and they’ll pour in hot water for you!

FAQs - booking Wailea flights

  • How long is the flight to Wailea?

    Flights from Seattle6h 00m
    Flights from Oakland5h 10m
    Flights from San Francisco5h 16m
    Flights from Los Angeles5h 29m
    Flights from Sacramento5h 14m
  • What is the cheapest flight to Kahului?

    In the last 3 days, the cheapest flight deal to Kahului was found on the route from San Diego, at $238 return. The most popular connection is from Los Angeles to Kahului and KAYAK users have found round-trip deals for as low as $277 in the last 3 days.

  • Which airlines fly to Kahului?

    Many airlines fly to Kahului, the most common ones being Hawaiian Airlines, Southern / Mokulele, and Southwest. See the amount of flights per week for popular airlines flying to Kahului.

  • How to fly to Wailea?

    You cannot fly directly to Wailea. KAYAK recommends you fly to Kahului (OGG) (14.41 miles from Wailea). From there you can rent a car or get a taxi.

  • What airports are near Wailea?

    The closest airport is Kahului (OGG) (14.41 mi). Other nearby airports are Kapalua West Maui (JHM) (24.17 mi), Hana (HNM) (28.36 mi), Lanai City (LNY) (33.67 mi) or Kalaupapa (LUP) (49.81 mi). KAYAK recommends you fly to Kahului.

  • How far is Kahului Airport from central Kahului?

    There are 3 miles between Kahului city center and Kahului Airport.

  • What is the name of Kahului’s airport?

    Kahului is served by Kahului Airport, also commonly referred to as Kahului or Maui Kahului. The airport code is OGG.

  • How does KAYAK find such low prices on flights to Wailea?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Wailea.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Wailea?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Wailea is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Wailea?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Wailea with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Wailea?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Wailea up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Wailea

  • There is no major airport in Wailea. It is instead served by Kahului Airport.
  • Looking for cheap airfare to Wailea? 25% of our users found round-trip tickets to Wailea for the following prices or less: From Los Angeles $743, from San Francisco $1,047, from Denver $1,793
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Wailea flight deals.

Top 5 airlines flying to Wailea

Need help choosing which airline to fly with from the United States to Wailea? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 9848 reviews
7.9Comfort
8.5Crew
8.2Boarding
7.1Entertainment
7.1Food
Airline reviews

the flight was delayed twice and then delayed from taking off.

2.0 MediocreRonald, Apr 2025SNA - SFO
Read more Alaska Airlines reviews

the flight was delayed twice and then delayed from taking off.

Plane was delayed and got me in past bedtime. But more importantly, my tsa precheck number wasn’t on my ticket so had to deal with the general line. Oh well, guess the delay helped that situation.

The Crew was super nice but the plane was subpar at best. Filthy in some aspects. Internet only worked half the time and not with everything.

It was as good as flying can be, which is still very uncomfortable. Clean new aircraft, great crew.

1.5 hour delay boarding plus 1+ hour sitting in plane waiting for ground crew to load luggage and freight, made for 3:00AM arrival in Seattle.

The second leg of my trip left without me despite being my inbound transfer only a few minutes late. My friends told the gate agent and they closed the doors and left early anyway. Then they tried to rebook me on a flight SIX hours later which only changed when I got a supervisor to make it 4 hours later. The gate agent was nasty, unhelpful, and walked away from me.

They were all very kind, but misinformed. We came from Idaho to Spokane, Washington and were told that my husband and I could get passes to sit with William until his flight took off. (William has special needs.) When we got to the airport we were told only one of us could sit with William, so my husband and I were separated for 2 hours as I sat with William. What is WORSE . . . is I asked for a meet and assist in Portland and they NEVER showed up. NOR did they call me to tell me they hadn't met him. William's grandmother in Portland is disabled and can't walk into find him. Fortunately, some kind citizens helped him to find the meeting point with me on the phone in terror. I have a heart condition, complete with prior heart attack, this type of customer service is UNACCEPTABLE.

Worst part is being squashed in a seat ( I am not fat) and unable To get comfortable

It was alright other than the changes in the Alaska Lounge. That and the migraine I had were disappointing. Other then that everything went well.

Took forever to get on board. Flights was one hour late.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Liked the crew. Seats were uncomfortable during the last few hours of the 11 hour flight. Better selection of movies .

They cancelled our flight and one after and then crammed everyone on a late flight. Refused to give us a meal voucher because the delay was less than 3 hours. In the end the delay was 4 hours. No reason was ever given for the cancelled flights. Fly Southwest!

The temperature on the plane was too cold and the food was not very good. Everything else was good.

There was mention of a complimentary magazine but none were in the seat pockets. The flight is short so understandable not having food or a snack.

Flight delayed. Then left much later than new time. 88 year old dad waiting at Kona airport for ages.

This is my first time flying Hawaiian. It was so disorganized and poorly coordinated, resulting in the most unacceptable delay

It’s really tough when you purchase tickets and you are unable to purchase your seats, and just get random seats when you are traveling with someone.

The flight from HON to Hilo caused a few problems, but we were helped by the checking agent at Hawaiian Airlines with tech assistance. My wife & I are in our 70's and not QR code savvy. But we are learning.

The service was great and the crew was so friendly and attentive!

Flight attendants were friendlier than on previous flight from HNL-BOS

The gate attendant let me walk right by her with a bag too big for the overhead compartment

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

Food and flight attendents with positive dispositions and friendly behavior, more professional attitudes

The gate was too far away for the connecting flight

Compared with other carriers business class for an overnight was not worth the extra expense.

Generally good. The aisles have gotten narrower which can slow down boarding. Flight crew was great! Healthier complimentary snacks would be appreciated. Due to earthquake in San Francisco we had to circle in air space for a bit but then had a smooth landing. I laud the flight crew for their patience ;)

Easy to board. Flight was super crowded though so I didn't sleep well on that cross country red-eye flight. The aisles seem ot have gotten narrower and the seat smaller whn luggage and people are getting bigger so it would be AWESOME to have more space and breathing room in general ;)

We boarded but then sat there waiting on some missed connection people to get on so we sat for about 15 minutes for that. Then we sat again because the passenger manifest was wrong and they had to figure it out before we could leave. That took about another 20 minutes or so. The crew was working hard to figure it out so it’s not their fault. It ended up being a system glitch where someone was upgraded to first class while another person was also in the same seat and it just created a mess that took a little while to figure out. They literally went to every person on the plane asking their names to see who was sitting in the wrong seat. I also hate the entertainment that must be watched on your phone or tablet. Just give us setback screens. It’s so much better. Almost every Delta flight has this now and it is so nice to have them. The crew did a great job. I have no complaints from them. They were very hard working, even with the mishap and a disgruntled passenger.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

My priority checked bag was not loaded on the flight. I had to sit in baggage claim in Las Vegas for 2 1/2 hours waiting for the next flight. All baggage staff were very helpful, tracking showed it as scanned for loading. Nobody told me why it wasn't on my flight.

They lost my luggage and it didn’t get delivered until the next day.

Would have thought that they would gas up plane before everyone got on board

3 hours late. Not even water offered on a 2.25 hour flight.

I had a carry on and a personal bag. I put my personal item under my seat and on way to the seat I put my bag up. I usually close my eyes and rest as I was on call for last 36 hours. I heard very loud announcements that someone needs to identify their bag. Pretty sure it was not mine until the hostess pointed out my jacket details attached to the bag. I asked why she got my bag out. I got berated and did not want to create a scene. But this person needs to be talked to.

Terrible. The flight was delayed two hours due to weather. Then when we got on the plane, the first pilot ended up timing out and we had to wait for a second pilot. Second pile came on board and we tax it out. Had to return back to the gate because of an unruly passenger. Then the copilot timed out. Had to wait for new copilot. Also had to wait for maintenance to check for fuel. Then found out the second pilot timed out and we had to wait for a third pilot. Was ready to go and then needed maintenance again for another issue. In the end, it was 2 o’clock in the morning when they announced that the flight couldn’t go because the third pilot and the second copilot had timed out.

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

American Airlines initially postponed the flight. Then they cancelled it an rescheduled us on a flight that would take over 24 hours with multiple stops. They then changed this flight to a reasonable alternative the next day which they later cancelled and replaced with a flight that would take off with an additional 16 hour delay. They blamed weather but I noticed (at 4am) that Delta had direct flights from Charlotte to Detroit. I went on line. Booked it and was in Detroit buy 9am. The interesting thing is they did a similar thing to a family member just 2 days earlier. I don't think I will fly American unless I have to.

Wonderful crew and early arrival to our destination. It was so nice to have free wifi access and movies too. Thank you!

Very friendly and efficient and smooth boarding. We were even way early arriving at my destination. Thank you.

The trip was very smooth and they provided great customer service

Everything you need to know for your flight to Wailea

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