$63 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 7/20. 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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1 adult, Economy

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Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Wailea

Wed, Sep 24 - Mon, Sep 29
Hawaiian Airlines Logo
6:59 pm - 10:03 pmSAN-OGG
6h 04mnonstop
Hawaiian Airlines Logo
11:09 pm - 7:30 amOGG-SAN
5h 21mnonstop
$250Hawaiian Airlines
Find Deal
Mon, Sep 1 - Tue, Sep 30
Hawaiian Airlines Logo
6:59 pm - 10:03 pmSAN-OGG
6h 04mnonstop
Hawaiian Airlines Logo
11:09 pm - 7:30 amOGG-SAN
5h 21mnonstop
$252Hawaiian Airlines
Find Deal
Tue, Sep 2 - Thu, Sep 11
Alaska Airlines Logo
5:50 pm - 6:17 amSAN-OGG
15h 27m1 stop
Alaska Airlines Logo
11:09 pm - 7:30 amOGG-SAN
5h 21mnonstop
$263Alaska Airlines
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Wed, Sep 24 - Mon, Sep 29
Alaska Airlines Logo
2:03 pm - 8:39 pmSAN-OGG
9h 36m1 stop
Alaska Airlines Logo
9:39 pm - 9:59 amOGG-SAN
9h 20m1 stop
$269Alaska Airlines
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Wed, Sep 3 - Mon, Sep 8
Delta Logo
7:30 am - 5:08 pmSAN-OGG
12h 38m1 stop
Delta Logo
9:10 pm - 1:02 pmOGG-SAN
12h 52m1 stop
$277Delta
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Wed, Sep 3 - Mon, Sep 8
Delta Logo
7:30 am - 5:08 pmSAN-OGG
12h 38m1 stop
Delta Logo
9:10 pm - 12:17 pmOGG-SAN
12h 07m2 stops
$282Delta
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Tue, Nov 18 - Tue, Nov 25
American Airlines Logo
6:37 am - 2:44 pmSAN-OGG
10h 07m1 stop
American Airlines Logo
11:00 pm - 8:33 amOGG-SAN
7h 33m1 stop
$332American Airlines
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Tue, Sep 23 - Tue, Sep 30
United Airlines Logo
10:54 am - 6:59 pmSAN-OGG
11h 05m2 stops
United Airlines Logo
1:20 pm - 11:41 pmOGG-SAN
7h 21m1 stop
$342United Airlines
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Tue, Oct 21 - Thu, Oct 30
United Airlines Logo
1:00 pm - 7:10 pmSEA-OGG
9h 10m1 stop
United Airlines Logo
1:40 pm - 12:59 amOGG-SEA
8h 19m1 stop
$347United Airlines
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Wed, Nov 26 - Wed, Dec 3
American Airlines Logo
6:40 am - 1:12 pmSFO-OGG
8h 32m1 stop
American Airlines Logo
11:00 pm - 12:32 pmOGG-SFO
11h 32m1 stop
$347American Airlines
Find Deal
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Good to know - Book Cheap Wailea Plane Tickets

Low seasonJanuary
High seasonJuly
Cheapest flight$63
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 7% 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 
KimberleyFlew with Alaska AirlinesSEA-OGGNov 2024
Pack snacks and patience. Ear plugs or noise-cancelling headphones are a must!
BryanFlew with Alaska AirlinesSAN-OGGMay 2024
Airlines are becoming much stricter in limiting people to one carry-on bag and one personal item.

FAQs - booking Wailea flights

  • How long is the flight to Wailea?

    Flights from Seattle5h 56m
    Flights from San Diego5h 41m
    Flights from San Francisco5h 10m
    Flights from Portland5h 39m
    Flights from Los Angeles5h 26m
  • 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 $250 return. The most popular connection is from Los Angeles to Kahului and KAYAK users have found round-trip deals for as low as $298 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 Denver $655, from Los Angeles $866, from San Francisco $1,010
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Wailea flight deals.

Reviews of the 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 10000 reviews
8.1Boarding
8.5Crew
7.8Comfort
7.1Food
7.1Entertainment
Airline reviews

Alaska app and website had numerous problems so couldn’t get boarding passes or check seats

8.0 ExcellentJoseph, Jun 2025EUG - LAX
Read more Alaska Airlines reviews

Alaska app and website had numerous problems so couldn’t get boarding passes or check seats

Flight was very warm. It felt like there was no working AC.

I liked the food. The WiFi was out and the flight was late.

Very bad, terrible food and late by 2 hours. Then no to open aircraft doors

Flying on Hawaiian Airlines was good. But, getting a boarding pass was a hassle. I booked what I thought was an Alaska Airlines flight that was actually a Hawaiian Airlines flight. I couldn't check in online. I had to wait for the Hawaiian Airlines counter to open so I could get my boarding pass which was a requirement for me to get in The Club or the Centurion Lounge. (I had no check in luggage so I didn't expect to have to physically check in.) The Alaska Airlines staff blamed the FAA for the problem.

Terrible check in experience, and they ended up losing our bag.

they didn't fix a plane and we were delayed travelling an extra 12 hours.

This flight was how a flight should be. The flight from Hawaii to Seattle was terrible

Our big luggage never made it to Boston. Very crucial to get it ASAP as heart medication is in there.

Wish I got An email stating that I needed to check in at hawaiian even if I made my ticket thru alaska. I had to walk to terminal A from Terminal B.

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Boarding was organised and relaxed. Crew were fantastic! Seats were lacking padding causing butt pain and stiffness.

I like for how they process during check in. It was very smoothly.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Check in process was a mess. Long lines, equipment malfuctioning. One line for baggage tags then a second line for bag checkin.

It was very pleasant. The staff and crew are very polite.

Hawaiian Airlines staff is always professional & quick & easy check in & boarding process

Customer service by Susan of Alaskan Air was outstanding. We missed our flight out of JFK. She got us rebooked the following day. Way to go Susan.

Bar code for checking luggage and boarding pass didn't work. Had to stand in long customer service line. Passengers at Oahu should be aware the Terminal for Hawaiian Air requires travel by shuttle. Budget an extra 20-30 minutes to get from the main terminal to the remote terminal.

Checking baggage at Honolulu was a real mess. No signs directing where to go.

We boarded an hour and a half late because a coffee maker leaked in the plane. Then we had to wait for awhile to get off the plane because another plane was in our spot at the terminal. I had plans when I landed that I had to skip so it was pretty disappointing.

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.

Why wasn't this flight departure scheduled eith another crew so that it could leave on time? When we arrived in Denver we had so little time between flights we had run to the connecting flight. We should received some credit for the inconvenience.

Really good 😊 the woman at the gate entrance was a little rude checking in our carry-on but i dont think she worked for the airline, she worked for the airport at sacramento, other than that amazing.

Gate agent did not hold flight for connection, provided no assistance to get new flight

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

United airlines, mediocre at best. No issues , nothing great . Worked for me

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Pretty bad gate mgmt upon arrival. No open gates and we had to wait at midnight. Shouldn’t be a surprise that an aircraft is coming in.

We started with trouble checking in 24 hours early. Then my husband did not get his TSA precheck. Finally flight delayed due to no crew. I know things happen

Boarding was very efficient. Everyone got on board and we got on our way very quickly. It was frustrating that the entertainment app was not functioning properly. I was not able to activate some of the movies offered. The crew on this flight appears to be pretty grumpy. They had no smile on their faces. I felt like they were doing us a favor for being there.

Mechanical delay and no compensation. Missed connection as a result of their delay. Mediocre performance and service. Horrible airline currently with horrible culture.

Comfortable plane ride however on delays disappointment no real details as to why the delays when other flights are leaving the airport

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

They changed our Gate 5 times, and concourse twice. Changed our seats twice.

Delayed because of weather in Nashville. I think God or some higher power generally has cursed me when it comes to flying out of Charlotte on American. I'm delayed pretty much everytime. We need Team Cobra Kai types to come in and "sweep the leg(s)" of the Charlotte ops people on principle. Don't let the sweet southern rocking chairs fool you, Charlotte is a sinkhole

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

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