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Find cheap flights to Wailea from $108

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 8/20. 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.
1 adult
0 bags
Wed 7/3
Wed 7/10

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Low season

January

High season

July

Cheapest flight

$108
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from San Diego to Kahului

FAQs - booking Wailea flights

  • How long is the flight to Wailea?

    Flights from San Diego5h 37m
    Flights from Seattle5h 55m
    Flights from San Francisco5h 10m
    Flights from Honolulu0h 40m
    Flights from Los Angeles5h 27m
  • 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 $108 one-way and $209 return. The most popular connection is from Los Angeles to Kahului and KAYAK users have found round-trip deals for as low as $244 in the last 3 days.

  • Which airlines fly to Kahului?

    Hawaiian Airlines, Southern / Mokulele, and Southwest usually have the most frequent connections from United States to Kahului. 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 from central Kahului?

    There are 3 miles between Kahului city center and Kahului.

  • What is the name of Kahului’s airport?

    Kahului is served by Kahului, 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.
  • 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 9197 reviews
8.6Crew
7.3Entertainment
7.9Comfort
8.2Boarding
7.3Food
Airline reviews

When Alaska uses Sky west which it does on many flights in and out of PDX, The planes use " Gates" that are outside of the terminal and are a long walk to and from the planes. Also you must board and deplane using a ramp. I have difficulty walking so going into Portland was difficult. Going out was worse . We walked to nearly the emd of this "Tunnel " only to be told there was a problem with the plane so we had to take the long walk back to to the terminal and then back out again when the plane was fixed. I will look for a Southwest flight next time I go to Portland

2.0 MediocreAnonymous, Jun 2024PDX - OAK
Read more about Alaska Airlines reviews

When Alaska uses Sky west which it does on many flights in and out of PDX, The planes use " Gates" that are outside of the terminal and are a long walk to and from the planes. Also you must board and deplane using a ramp. I have difficulty walking so going into Portland was difficult. Going out was worse . We walked to nearly the emd of this "Tunnel " only to be told there was a problem with the plane so we had to take the long walk back to to the terminal and then back out again when the plane was fixed. I will look for a Southwest flight next time I go to Portland

It was all good until they had a mishandling issue with a couple of our bags but overall it was fine and we got the bags eventually

Loved the airport. The announcements for boarding were too loud & echoing in the large waiting area, so hard to follow. Other than that, we had a great experience.

First time traveling with them and they were great leaving on time arriving on time very clean planes 😊

I had very little legroom and the only food available was really salty

Great! No issues at all. Friendly staff, on time flight, and smooth, comfortable flight.

Staff was very friendly. Flight was on time and arrived early. Flight was comfortable.

The airline itself was extremely comfortable and the staff were wonderful. The communication was excellent amongst the pilots and flight attendants and the passengers. I was throughly impressed by the cleaning crew that came on the plane immediately to ready it for the next flight. I have flown a bunch of times post Covid pandemic and have never seen this! I gave the “okay” rating for the food and entertainment because I didn’t order food and there wasn’t entertainment offered through the plane (only your personal devices).

The flight both ways was pleasant and uneventful. The staff was friendly, accommodating, and overall very helpful.

Offer snacks/meals for people with food sensitivities. HAVE TV SCREENS!

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The crew was quick and efficient. The flight was uneventful and arrived slightly early.

My seat was broken I couldn’t put it back I have really bad back issues , the flight was 5 hours delayed and there was a drink dude harassing the entire flight

No food or entertainment because it was a short flight. Unfortunately the takeoff was delayed more than an hour

Parents with kids should all be in the same area. Sounds rude but who what's to fly 6hrs with crying and bratty kids. Just my opinion.

Ok, so I didn’t have seats, so got there very early. I was first in line only to be told, listen for your name for seats. The flight was boarding before they gave me a middle seat, way after others showed up who were given more favorable treatment. Ok, so , don’t show up early and obey all the rules??? Clearly, your gate clerks did not. What gives???

Short flight but delayed. Since its a short flight no food or entertainment necessary

We had an awesome flight attendant who came by and made sure we were okay. Checked on us often and even shared some snacks that she had brought on, like edamame with chili and garlic seasoning. Yummy!

Overall good experience. I'm just over 6ft with long legs and legroom could be better, but is on par with other airlines. Only real negative was turbulence but that's not the airlines fault.

First flight got cancelled. Got booked for another flight departing 3.5 hours later which ended up being 1hr delayed... The flight was good when we finally ended up flying.

Very friendly und helpful crew. Looking forward for some more flights in

Flight was delayed due to the late arrival of the catering truck, which is quite unacceptable. There was a beverage service, but no pretzel, or cookie, or nuts were served in coach.

Not worth the price of premium class ticket paid, felt more like steerage.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

The Wi-Fi was unavailable on this flight for some reason.

On time take off…US cabins look tired and need of refresh!

Fantastic. Smooth boarding with an infant. Never experienced it with any other carriers.

Equipment swap led to 2+ hour delay on international flight. And to top it off, boarding took forever.

Wretched scheduling - they got themselves into a critical crew situation and didn’t try to address it until 15 minutes before they had to cancel my flight

They cancelled two flight and got us onto another airline, which was also delayed.

Nothing, terrible travel experience due to weather and maintenance delays and was left stranded in Austin.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

28 hour delay at Fort Worth/Dallas airport, part due to weather which was unavoidable, but various other reasons - no pilot, no fa, mechanical problem, plane too small, too big, crew out of flying time, seat configuration problems.... endless and hourly updates with a different excuse. Finally told us about 3.00 am, that the flight was delayed to hours later.

Experience was bad. 3.5 hour delay for a 2.5 hour trip. There was no r Transparency about the reason for the delay and it was done 30 mins at a time.

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

There were delays on both ends. It made it less than excellent. This plane was great though

AA1537 the AC was not working properly. It was very hot and uncomfortable.

Book Cheap Wailea Plane Tickets

Recent round-trip flight deals

8/20Tue
nonstopAlaska Airlines
5h 27mSFO-OGG
8/27Tue
nonstopAlaska Airlines
4h 52mOGG-SFO
$209
8/27Tue
1 stopHawaiian Airlines
7h 18mSFO-OGG
9/4Wed
nonstopHawaiian Airlines
5h 00mOGG-SFO
$214
8/28Wed
1 stopUnited Airlines
7h 57mSAN-OGG
9/4Wed
1 stopUnited Airlines
8h 04mOGG-SAN
$216
9/4Wed
nonstopUnited Airlines
5h 17mSFO-OGG
9/25Wed
1 stopUnited Airlines
7h 35mOGG-SFO
$218
8/24Sat
1 stopAmerican Airlines
9h 56mONT-OGG
8/29Thu
1 stopAmerican Airlines
8h 08mOGG-ONT
$240
8/20Tue
1 stopDelta
9h 43mSFO-OGG
8/28Wed
1 stopDelta
8h 44mOGG-SFO
$242
9/11Wed
1 stopDelta
9h 18mSJC-OGG
9/18Wed
1 stopDelta
12h 25mOGG-SJC
$242
8/29Thu
1 stopAmerican Airlines
10h 11mSAN-OGG
9/26Thu
1 stopAmerican Airlines
7h 29mOGG-SAN
$246
7/16Tue
nonstop
6h 02mSEA-OGG
7/24Wed
nonstop
5h 35mOGG-SEA
$332
7/10Wed
2 stops
16h 39mONT-OGG
7/17Wed
2 stops
13h 55mOGG-ONT
$604

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Recent one-way flight deals

8/20Tue
1 stopUnited Airlines
7h 49mSAN-OGG
$108
8/20Tue
nonstopHawaiian Airlines
5h 50mSAN-OGG
$114
8/21Wed
nonstopAlaska Airlines
5h 59mSAN-OGG
$119
8/21Wed
1 stopDelta
12h 29mSAN-OGG
$128
8/31Sat
nonstopAlaska Airlines
5h 57mLAX-OGG
$129
6/8Sat
nonstopDelta
5h 35mLAX-OGG
$131
7/28Sun
nonstopUnited Airlines
5h 29mSFO-OGG
$139
8/19Mon
nonstopHawaiian Airlines
5h 25mSJC-OGG
$139
8/31Sat
1 stopAmerican Airlines
28h 47mSFO-OGG
$172
6/6Thu
nonstopAmerican Airlines
5h 47mLAX-OGG
$181

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Last minute flights to Wailea

Last minute flight, train and bus deals

6/3Mon
nonstopAmerican Airlines
5h 37mLAX-OGG
10/17Thu
nonstopAmerican Airlines
5h 21mOGG-LAX
$259
6/3Mon
multi-stopUnited Airlines
8h 18mLAX-OGG
10/17Thu
nonstopUnited Airlines
5h 23mOGG-LAX
$268
6/3Mon
nonstopDelta
5h 44mLAX-OGG
6/10Mon
multi-stopDelta
11h 07mOGG-LAX
$270
6/3Mon
nonstopDelta
5h 44mLAX-OGG
6/12Wed
multi-stopDelta
12h 50mOGG-LAX
$272
6/3Mon
multi-stopUnited Airlines
8h 18mLAX-OGG
10/17Thu
multi-stopUnited Airlines
8h 34mOGG-LAX
$308
6/4Tue
nonstopAmerican Airlines
5h 37mLAX-OGG
6/4Tue
multi-stopAmerican Airlines
10h 31mOGG-LAX
$315
6/3Mon
nonstopAlaska Airlines
5h 24mSFO-OGG
6/3Mon
nonstopAlaska Airlines
5h 08mOGG-SFO
$351
6/3Mon
nonstopAlaska Airlines
5h 24mSFO-OGG
6/6Thu
nonstopAlaska Airlines
5h 08mOGG-SFO
$357
6/3Mon
nonstopHawaiian Airlines
5h 35mLAX-OGG
6/24Mon
nonstopHawaiian Airlines
5h 15mOGG-LAX
$364
6/3Mon
nonstopHawaiian Airlines
5h 35mLAX-OGG
6/12Wed
nonstopHawaiian Airlines
5h 15mOGG-LAX
$365

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Flights to Wailea

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