$129 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 5/28. 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.
Alaska Airlines Logo
4:27 pm - 7:35 pmSAN-OGG
6h 08mnonstop
Alaska Airlines Logo
11:13 pm - 7:35 amOGG-SAN
5h 22mnonstop
$248Alaska Airlines
Find Deal
Tue, May 13 - Wed, May 21
Hawaiian Airlines Logo
4:27 pm - 7:35 pmSAN-OGG
6h 08mnonstop
Hawaiian Airlines Logo
12:45 pm - 11:30 pmOGG-SAN
7h 45m1 stop
$253Hawaiian Airlines
Find Deal
Wed, May 14 - Wed, May 21
Alaska Airlines Logo
4:27 pm - 7:35 pmSAN-OGG
6h 08mnonstop
Alaska Airlines Logo
11:13 pm - 7:35 amOGG-SAN
5h 22mnonstop
$258Alaska Airlines
Find Deal
Tue, May 13 - Mon, May 19
Hawaiian Airlines Logo
2:00 pm - 10:25 pmSAN-OGG
11h 25m1 stop
Hawaiian Airlines Logo
12:45 pm - 11:30 pmOGG-SAN
7h 45m1 stop
$263Hawaiian Airlines
Find Deal
Wed, May 14 - Wed, May 21
Delta Logo
2:10 pm - 7:25 pmSAN-OGG
8h 15m1 stop
Delta Logo
9:30 pm - 1:00 pmOGG-SAN
12h 30m1 stop
$267Delta
Find Deal
Tue, May 13 - Wed, May 21
Delta Logo
9:47 am - 7:25 pmSAN-OGG
12h 38m2 stops
Delta Logo
9:30 pm - 1:05 pmOGG-SAN
12h 35m1 stop
$272Delta
Find Deal
Tue, May 13 - Tue, May 20
United Airlines Logo
4:44 pm - 7:11 pmSFO-OGG
5h 27mnonstop
United Airlines Logo
7:00 am - 3:00 pmOGG-SFO
5h 00mnonstop
$278United Airlines
Find Deal
Mon, May 26 - Thu, May 29
United Airlines Logo
6:00 am - 10:55 amSFO-OGG
7h 55m1 stop
United Airlines Logo
10:33 pm - 6:35 amOGG-SFO
5h 02mnonstop
$288United Airlines
Find Deal
Tue, Aug 12 - Tue, Aug 26
American Airlines Logo
5:50 am - 2:02 pmSFO-OGG
11h 12m1 stop
American Airlines Logo
10:00 pm - 10:33 amOGG-SFO
9h 33m1 stop
$297American Airlines
Find Deal
Wed, Aug 13 - Wed, Aug 20
American Airlines Logo
5:50 am - 2:02 pmSFO-OGG
11h 12m1 stop
American Airlines Logo
10:00 pm - 8:41 amOGG-SFO
7h 41m1 stop
$323American Airlines
Find Deal
Tue, Aug 19 - Wed, Aug 27
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Good to know - Book Cheap Wailea Plane Tickets

Low seasonJanuary
High seasonJuly
Cheapest flight$129
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 9% 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 Seattle5h 57m
    Flights from San Diego5h 42m
    Flights from San Francisco5h 13m
    Flights from Los Angeles5h 26m
    Flights from Sacramento5h 13m
  • 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 $248 return. The most popular connection is from Los Angeles to Kahului and KAYAK users have found round-trip deals for as low as $291 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.

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 $897, from San Francisco $1,039, from Denver $1,818
  • 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 9968 reviews
8.2Boarding
7.1Entertainment
7.9Comfort
7.1Food
8.5Crew
Airline reviews

It was all great all around. Will travel with Alaska next trip.

10.0 ExcellentLoyola, Apr 2025BOS - SEA
Read more Alaska Airlines reviews

It was all great all around. Will travel with Alaska next trip.

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

Everything was good. However, the selections of movies and TV shows were boring and unexciting. It was disappointing.

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

There was no seating at the gate, no where to charge your devices, super crowded. Boarding in group F meant all luggage space was taken when it was time for me to board. The boarding crew was short with everyone and seemed irritated. The luggage space was insufficient, the seat was too small for me (6'4") and very uncomfortable trip. I was in a middle seat between a person snoring the whole trip and a person with very strong body odor. The flight crew was terse and unfriendly, seemed irritated and impatient. Yelled a lot at people with earbuds in, understandable. Finally, we arrived 10 minutes early, only to sit on the tarmac for 20 minutes and wait for a gate. Worst flight experience I've had in years.

I made a mistake. Read what I wrote in the flight from Dulles to SEA. The negative experience was from SEA to BOI. Total garbage. Wont do it again.

Flight 351 SEA to BOI was terrible. We got to cruising altitude and I needed to use the restroom but the fasten seatbelt sign never came off. There was no turbulence and I'd felt the plane level off so I stood up to use the restroom about 15 minutes after we leveled off. The stewardess went over the intercom and said I needed to be seated because the captain hadn't turned off the fasten seatbelt sign....Which... Fair.... But not five minutes later she went and used the bathroom. Felt very unprofessional to leave a paying customer with a burning urethra for the entire flight and bark at them to sit down and still use the bathroom yourself. They never did turn off the seatbelt sign.

For longer trips, snacks are puny, boring and don’t have ANY nutritional value.

One of the worst check-in experiences ever. Apparently, we were overweight and had to completely repack. They tried to charge us an extra $35 per bag on top of the standard checked baggage fee we had already paid in advance. Surprisingly, we managed to fit everything into our carry-ons and stayed under their precious 50-pound limit. (By the way, 23 kg is actually 50.7 lbs, so we couldn’t even go slightly over 50 according to the very unfriendly agent.)

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

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.

We moved from the international terminal to a new location. I think there are still some bugs to work out . We didn’t receive check in notification and had to scramble to find it but i think it will work out

Not so good. The takeoff was aborted after reaching 100 knots due to a problem with the front tires. I do commend the pilot for a quick decision and preventing a potential disaster. We returned to the gate to put fresh tires on the front. Our flight was delayed for over 3 hours. The rest of the flight was okay. We were reimbursed by Hawaiian Airlines for only $50. Not too generous

Arrived at the gate with no seats assigned. Was told by gate agent the flight was full and we would not be on it. I asked the gate agent how could I be sold tickets when the flight was full. She replied, “Thats just how they do it.” I was able to get seats once I arrived at the gate. The flight itself was great. I’ll never purchase tickets without seat assignments from kayak or anyone again. Shame on kayak or Hawaiian airlines or all of you.

A cold sandwich would be much better than the warm gummy croissant.

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

A bit rush for transit. Food and entertainment are not available

Multiple delays and not straight answer from the United team

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

leg space better than expected. two washrooms for one plane isn't enough.

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

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

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