$99 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 5/5. 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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Good to know

Low season

October

High season

July

Cheapest flight

$99
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from San Francisco 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!
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 San Diego5h 47m
    Flights from Seattle6h 01m
    Flights from San Francisco5h 21m
    Flights from Portland5h 46m
    Flights from Los Angeles5h 32m
  • 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 Francisco, at $169 return. The most popular connection is from Los Angeles to Kahului and KAYAK users have found round-trip deals for as low as $195 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 $753, from San Francisco $897, from Denver $1,990
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly from the United States is January.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Wailea flight deals.
See more tips

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 9553 reviews
7.1Entertainment
7.2Food
8.2Boarding
7.9Comfort
8.5Crew
Airline reviews

Our flight was diverted to Spokane, WA bc our crew timed out. Then we were flown to San Francisco

2.0 MediocreAnonymous, Dec 2024EWR - SFO
Read more Alaska Airlines reviews

Our flight was diverted to Spokane, WA bc our crew timed out. Then we were flown to San Francisco

Your staff said the call button is for emergencies only now? Unreal. Also every one who welcomed me aboard was staring at their phone. Why even bother..

I was able to upgrade to first class, which was great. Food and drinks were underwhelming compared to other first class flights I have taken.

Cross country flight ... there was no entertainment system... for any flight over 4 hours there should be some entertainment. There were 2 drink and cookie services only (which is ok, but not special)

I purchased a flight to Hawaii, changing planes in San Diego. My flight change location was later changed to Seattle then on to Kona, adding hours to my already long flight. Also, my flight home was run through Portland rather than through San Diego, once again, adding hours to my flight. At 81 years old I don’t want hours robbed from me.

Not great. The flight was delayed, then when we were on the plane we spent over an hour taxiing before take off. We arrived very late and it took a long time for the luggage to arrive. I wish you all Happy Holidays though.

It was comfortable, the food was mediocre. Tasted like microwaved food.

Very crowded and very noisy . No way to really rest .

My flight was delayed. But it was during holidays so you kind of expect things like that to happen. I am not a frequently flyer so I am OK with that. But none the less, once the flight started, it seemed to me like it went fast. 😊

The planes were clean! The crew was good The boarding in Seattle was not good because the accent of the woman and the low volume of the speaker made it impossible to hear.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Everything was great. Great service, excellent communication, and early arrival

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

It was terrible, if they ran flights on time it would make a big difference.

The plane was very old. No screens on the back of the seat and there was obvious wear and tear in both the bathroom and the seating areas.

Plane had screws missing from engine cowling. Retire that POS

Some staff were very nice. Others were whatever. Plane was 2 hours delayed. Food was absolutely horrible. Nobody likes a turkey croissant. Gross. Serve something healthy and Hawaiian. Free internet was awesome but we only got that because we were 2 hours delayed. That should be standard on all flights, free internet. Luckily we made our connection but the plane on the connecting flight was ancient and had screws missing from the engine cowling. That plane needs to be retired.

They canceled our flight and reboot us for a later flight which threw off the rest of our plans

Friendly and helpful crew. But we departed 4 hours later than scheduled departure.

It was nice to have WiFi on board to steam on your device.

On time, pleasant crew For 45 minutes please don’t bother with single use plastic drink containers

The boarding was stressful without paying extra for an assigned seat. The staff were helpful but the process is unacceptable.

I love that every seat has a USB charger. The seats were comfortable and everyone was friendly! I can't think of anything I would improve.

Going to Kahalui was wonderful. Attendants were awesome. Coming home, I was bumped from the seat I originally booked. Imagine my embarrassment as I stood there knowing I booked my flight a month earlier. All in all, I didn’t allow that spoil a wonderful weekend in Maui with family.

EVen warmer in the plane it think it was 24+ degrees

Good flight. On time. Boarding and seating was easy. Crew were really friendly, yet professional. Bathroom (by cockpit) was small but serviceable. Some the seats were showing some notable wear & tear, but were comfy. Very happy UA customer. TY! 🤛🏽💗

Wish movie and music choices changed more often. Mostly same from a month or two ago when I last flew.

Overall, it was a good experience. Boarding was good and there was plenty of overhead bin space for everyone’s carryons (even when we boarded toward the end). Only improvement would be to offer trash service more regularly.

We arrived early and finally made it to our gate almost an hour after.

The reason I don’t fly United. No in seat entertainment for a long flight and inconsistent WiFi and entertainment available from my device.

We were delayed 3x and because I didn’t purchase my tickets directly from United Airlines I was told I Have to take care of it myself so I called Underpricer and they helped me but before I changed my flights I took the risk of sticking by what my tickets were and was lucky to have gotten on the original all flight with only 15 mins before take off. not sure if I will do this again

The planes are so dirty! Food crumbs and finger print smudges, Dust over the vents and carpet stains. It’s disgusting.

Everything good until we waited for jet bridge at SFO. Then pilot gets on speaker & said it won’t reach plane- too short, need to go to different gate. Then 5 min later, adjusted plane/jetbridge & all ok?!?

David went above and beyond to make our flight the best that it could be

AA had a nationwide tech glitch today and after two connections snd hours of delay, I arrived 7 hours late to my destination

It would have been better if I could have had my flight on time. It was delayed for 5 hours. Caused me to not be able to fulfill my promise to my granddaughters. Other than that it was a good trip.

Delayed due to no crew. On a major holiday travel day.

Was supposedly in main extra (row 10), but the seat spacing appeared to be regular economy (the head rest was blue, as well - same as economy, the seats in front of us had red head rests). Otherwise the flight was good and got in well ahead of schedule.

American was having a problem with their kiosks when I arrived which made the check-in and bag drop process unusually long. Additionally, they only had one person working check-in. Eventually, the kiosks were fixed and everything else went smoothly.

The flight got canceled last minute with no explanation or refund, I had to rebook for a different day

Flight was delayed multiple times and I chose to switch to another flight that had a layover. I finally arrived 7 hours later than I was supposed to.

This was a horrible American Airlines experience, and it discourages me from flying with them again. It may have stemmed from a mechanical delay, but it appeared that the team was unprepared to respond to the delay. After boarding, we waited an hour before finally taking off. After landing at our destination, we waited an additional hour on the tarmac waiting for a gate (at 8:00pm) to be assigned and cleared. The flight crew did their best, but they were clearly tired and also ready to be done for the day. Because of the delay, I missed a connecting flight. It was a very poor experience.

from Boston to Washington was good but return to Boston was terrible, Gate was changed and plane was so uncomfortable, I thought it would crash 🙈🤦‍♀️ also when I showed my bording pass they didn't know where to send me and finally gave me direction and at the plane they said to find free seat somewhere😬🤦‍♀️🫣

When my flight was delayed due to weather, I was rebooked to another flight since it showed that I would miss my connection. It was a lot of work to get back onto my originally connecting flight which was also delayed. That part caused a lot of stress and frustration. The ticketing agent at the desk was not very helpful.

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