$93 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 3/2. 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
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$241
Overall average: $317
Alaska Airlines
Sun 1/18Thu 1/22
SAN - OGG • 1 stop
Cheapest non-stop
$243
Typical prices: $237-$416
Alaska Airlines
Sun 1/4Wed 1/14
SAN - OGG • Non-stop
Top routes
SAN-OGG
Cheapest
LAX-OGG
Most popular
Insights
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We hope you love your trip to Wailea!
Flight Deals
Useful Info
Flight Deals

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

Sun, Jan 18 - Thu, Jan 22
Alaska Airlines Logo
6:43 am - 10:40 am
SAN
-
OGG
29h 57m1 stop
Alaska Airlines Logo
11:59 pm - 7:23 am
OGG
-
SAN
5h 24mnonstop
$241Alaska Airlines
Mon, Jan 5 - Mon, Jan 12
Alaska Airlines Logo
5:13 pm - 9:37 pm
SAN
-
OGG
6h 24mnonstop
Alaska Airlines Logo
12:18 pm - 9:46 pm
OGG
-
SAN
7h 28m1 stop
$242Alaska Airlines
Tue, Feb 17 - Mon, Mar 2
Alaska Airlines Logo
8:05 pm - 11:46 pm
SJC
-
OGG
29h 41m1 stop
Alaska Airlines Logo
11:54 pm - 5:33 pm
OGG
-
SJC
15h 39m1 stop
$242Alaska Airlines
Sun, Jan 11 - Thu, Jan 22
Delta Logo
9:50 am - 7:15 pm
SJC
-
OGG
11h 25m1 stop
Delta Logo
10:00 pm - 1:34 pm
OGG
-
SJC
13h 34m1 stop
$243Delta
Fri, Feb 27 - Tue, Mar 3
American Airlines Logo
9:45 am - 7:23 pm
SAN
-
OGG
11h 38m1 stop
American Airlines Logo
11:15 pm - 8:51 am
OGG
-
SAN
7h 36m1 stop
$247American Airlines
Wed, May 6 - Wed, May 13
Delta Logo
7:15 am - 5:49 pm
SJC
-
OGG
13h 34m1 stop
Delta Logo
11:30 pm - 6:17 pm
OGG
-
SJC
15h 47m2 stops
$249Delta
Fri, Jan 9 - Sun, Jan 18
Hawaiian Airlines Logo
7:00 am - 10:40 am
SFO
-
OGG
5h 40mnonstop
Hawaiian Airlines Logo
9:00 pm - 7:20 am
OGG
-
SFO
8h 20m1 stop
$269Hawaiian Airlines
Mon, Jan 12 - Sat, Jan 31
Hawaiian Airlines Logo
7:00 am - 10:40 am
SFO
-
OGG
5h 40mnonstop
Hawaiian Airlines Logo
11:50 am - 6:50 pm
OGG
-
SFO
5h 00mnonstop
$272Hawaiian Airlines
Mon, Feb 16 - Wed, Feb 25
American Airlines Logo
6:01 am - 10:08 pm
SEA
-
OGG
18h 07m1 stop
American Airlines Logo
11:15 pm - 11:05 am
OGG
-
SEA
9h 50m1 stop
$273American Airlines
Fri, Jan 23 - Sat, Jan 31
United Airlines Logo
8:35 am - 4:47 pm
MSP
-
OGG
12h 12m1 stop
United Airlines Logo
2:25 pm - 8:48 am
OGG
-
MSP
14h 23m2 stops
$448United Airlines
Useful Info

Good to know - Book Cheap Wailea Plane Tickets

Low seasonOctober
Cheapest flight$93
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 19% 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 Airlines
SEA
-
OGG
Nov 2024
Pack snacks and patience. Ear plugs or noise-cancelling headphones are a must!
BryanFlew with Alaska Airlines
SAN
-
OGG
May 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 Oakland5h 16m
    Flights from San Diego5h 52m
    Flights from Seattle6h 02m
    Flights from San Francisco5h 23m
    Flights from Los Angeles5h 34m
  • 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 $241 return. The most popular connection is from Los Angeles to Kahului and KAYAK users have found round-trip deals for as low as $276 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 $815, from San Francisco $849, from Denver $947
  • 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 11405 reviews
7.1Food
7.8Comfort
7.0Entertainment
8.5Crew
8.1Boarding
Airline reviews

Good. Flight was good. Crew was good. Wish they offered coffee refills. Wish I didn’t have to pay for headphones. Otherwise good for a commercial flight.

8.0 ExcellentAnonymous, Nov 2025
PHX - HNL
Read more Alaska Airlines reviews

Good. Flight was good. Crew was good. Wish they offered coffee refills. Wish I didn’t have to pay for headphones. Otherwise good for a commercial flight.

Should have been forthcoming for reason for delay. Should have been able to check in for seat I'd like.

It was fine. It was a 30 minute flight so there was water or fruit juice and no food. Which was totally fine. The check in, gate and flight crew were all excellent.

I didn’t order food so can’t really say how it was. Overall, it was a great experience.

It was a pleasant experience. Considering we paid over $3000 for first class there really wasn’t anything special about first class. All the seats looked the same and everyone got the same great customer service. The only thing that was different between first class and couch was the drinks and the meal. We wouldn’t waste that much $ on first class on that plane again.

Once again, Hawaiian Airlines upon checking in for our return flight, told us that we hadn’t paid for our extra comfort seats. This had happened on our incoming flight as well. Hawaiian Airlines had changed our flight and put us in standard seats. I sent them confirmation emails and receipts showing that I had paid for extra comfort seats and they ignored me and refused to accept my proof of payment. I ended up having to pay for our extra comfort seats again. On our return flight, once again, we were told we hadn’t paid for our extra comfort seats, which we had. I argued until a supervisor was summoned and researched further in their system and found that we had paid for them. If I hadn’t insisted, we would’ve been forced to buy our seats again or be assigned a standard seat. This kind of Customer Service is totally unacceptable. I would never use Hawaiian Airlines again if I have a choice.

Flight was delayed 14 hours! We missed an entire day of our vacation and had to pay for hotel that we didn’t use

Glad they offer free meal, & I got a complimentary drink I’d like coffee,tea, or water offered 3/4 into trip

Could not check in online. Called airline twice, thinking Hawaiian Airlines could check me in during phone call. NO. In 2nd phone call, Customer Service explained that due to “transition period” of Hawaiian Airlines/Alaska Airlines merger, I could only check in at the airport. In addition, flight to Kahului was late at arrival gate; I made connection to Lihue but my bag did not, so I had to return to Lihue airport a couple hours after my arrival to retrieve the bag.

The boarding was confusing because the PA system at PDX was so quiet you couldn’t hear anything being said . The seats were uncomfortable. The food was pretty bad and I normally don’t mind airplane food. The flight attendants were not friendly. I learned upon check in that Hawaiian airlines had reassigned our seats of the second leg of the trip. I had confirmed and paid for special seats but they put me and my companion on standard seats in different rows. Hawaiian also did the same on my return flight after the flight times had changed. I happened to go online to check my reservation and saw the flight had changed. I gad received no notice. I saw that my confirmed seats that I had paid extra were gone. After much back and forth with the airlines they refused to correct their error. I showed them confirmation documents of my seat reservation and receipt of payment but they refused to correct the seat change or reimburse me. I had to pay $200 again to reserve the original seats. Shameful and manipulative. They basically held me hostage. If I wanted to be in that flight I had to pay up.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

The crew was quite good, they came by often with drinks or to collect trash. But what wasn't nice was the flight was over weigh and several people had to be rebooked. I was questioned whether I should have a seat when I was getting to it. The in-flight entertainment kept buffering and interrupting. And the route took the airplane through high winds which caused us a longer flight

Wasn’t on the flight due to Alaska cancellation…also after all the rerouting, I was going to be on a later flight that left SFO at 7:47pm, which meant an almost 6 hour layover. That same Hawaiian flight was delayed for another 2hours.

I always love flying Hawaii and I have nothing to add

Everything was great and smooth. Given the short flight there was no entertainment but the rating does not give this option. My first flight with Hawaiian was a success all around.

comfortable but the food is horrible. I have flown Hawaiian several times now and no matter what they say the food is its the same squashed bread with melted goop inside. Tastes fake and isnt what they represent, its quite nasty. What happend to real food? And there is NO entertainment!! so not sure why they are asking for a review on that.

I was very, very cold and a stranger loaned me her sweater next to me. I didn’t wanna buy a blanket just for a four hour trip when I did not need the pillow or the earphones. I don’t mind purchasing a blanket, but I only needed that not all of it accessories. Cold air pretty much blew the entire trip. Two people in front of me both bought the blanket packages. Maybe that’s the idea. The crew was exceptionally nice and passed through multiple times.. the restrooms were very clean and usually accessible.

3 hour wait on customer service after flight was cancelled. Was bumped to a flight where I wouldnt have gotten to my destination for another 2 days. Had to fully refund flight and book a new one the following morning. Paid twice the amount for the flight than I had originally booked. Very disappointed I was not offered any sort of discount or points for all of the frustration, in fact the airline profited twice as much off of me by cancelling my flight and and changing my entire trip.

Very accommodating on flight changes when something came up. Definitely felt a notch above other airlines.

They we able to seat my companion and I next to each other. Plane’s temperature was very cool. Willl be more prepared on return trip.

What an amazing flight. I haven’t experienced this level of service in a flight in years. This will be the only way to fly to Hawaii for me in the future.

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Even though we were delayed, we were able to make our connection

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

Liked that it was on time. Staff professional and friendly.

Things were delayed a little. But that didn’t affect my plans. It was fine. I was surprised it was so full thanksgiving day. The crew were friendly and professional.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

Everything you need to know for your flight to Wailea