$151 Find Cheap Flights to Wailea - Compare and Save

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 10/21. 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
$302
Typical prices: $643-$420
Delta
Wed 9/23Tue 9/29
ONT - OGG • 1 stop
Cheapest non-stop
$355
Typical prices: $470-$345
American Airlines
Thu 9/3Mon 9/7
LAX - OGG • Non-stop
Arrival airport
You can't fly directly to Wailea. It is served by Kahului (OGG), located 14.4 miles from Wailea.
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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

Wed, Sep 23 - Tue, Sep 29
Delta Logo
6:20 am - 5:52 pm
ONT
-
OGG
14h 32m
1 stop
Delta Logo
8:05 pm - 8:53 am
OGG
-
ONT
9h 48m
1 stop
$302Delta
Sun, Sep 13 - Wed, Sep 23
Delta Logo
7:00 am - 5:49 pm
ONT
-
OGG
13h 49m
1 stop
Delta Logo
9:15 pm - 12:10 pm
OGG
-
ONT
11h 55m
2 stops
$308Delta
Tue, Nov 3 - Wed, Nov 11
Southwest Logo
5:50 am - 4:10 pm
ONT
-
OGG
12h 20m
2 stops
Southwest Logo
10:30 pm - 12:05 pm
OGG
-
ONT
11h 35m
1 stop
$350Southwest
Thu, Sep 3 - Mon, Sep 7
American Airlines Logo
6:37 pm - 9:19 pm
LAX
-
OGG
5h 42mnonstop
American Airlines Logo
10:49 pm - 7:05 am
OGG
-
LAX
5h 16mnonstop
$355American Airlines
Tue, Nov 3 - Wed, Nov 11
Southwest Logo
5:50 am - 4:10 pm
ONT
-
OGG
12h 20m
2 stops
Southwest Logo
9:25 pm - 10:40 am
OGG
-
ONT
11h 15m
2 stops
$355Southwest
Fri, Aug 28 - Sun, Aug 30
American Airlines Logo
9:03 am - 11:46 am
LAX
-
OGG
5h 43mnonstop
American Airlines Logo
10:54 pm - 7:10 am
OGG
-
LAX
5h 16mnonstop
$357American Airlines
Wed, Sep 9 - Mon, Sep 14
United Airlines Logo
12:41 pm - 7:20 pm
SAN
-
OGG
9h 39m
1 stop
United Airlines Logo
7:00 am - 8:02 pm
OGG
-
SAN
10h 02m
2 stops
$382United Airlines
Thu, Aug 27 - Tue, Sep 1
Alaska Airlines Logo
6:34 pm - 9:37 pm
SAN
-
OGG
6h 03mnonstop
Alaska Airlines Logo
10:40 pm - 7:01 am
OGG
-
SAN
5h 21mnonstop
$395Alaska Airlines
Wed, Nov 4 - Wed, Nov 11
United Airlines Logo
1:16 pm - 8:06 pm
SEA
-
OGG
8h 50m
1 stop
United Airlines Logo
11:45 pm - 10:21 am
OGG
-
SEA
8h 36m
1 stop
$395United Airlines
Mon, Aug 17 - Mon, Aug 24
Alaska Airlines Logo
6:55 pm - 9:55 pm
SAN
-
OGG
6h 00mnonstop
Alaska Airlines Logo
10:40 pm - 7:01 am
OGG
-
SAN
5h 21mnonstop
$399Alaska Airlines
Useful Info

Good to know - Book Cheap Wailea Plane Tickets

Low seasonJanuary
Cheapest flight$151
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Long Beach to Kahului

Flights to Wailea: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Wailea 
GFlew with Hawaiian Airlines
SEA
-
OGG
Mar 2026
Bring your own food on the plane. Don't expect much.
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 San Diego5h 45m
    Flights from San Francisco5h 20m
    Flights from Portland5h 55m
    Flights from Long Beach5h 36m
    Flights from Los Angeles5h 34m
  • What is the cheapest flight to Kahului?

    In the last 5 days, the cheapest flight deal to Kahului was found on the route from Long Beach, at $302 return. The most popular connection is from Los Angeles to Kahului and KAYAK users have found round-trip deals for as low as $355 in the last 5 days.

  • Which airlines fly to Kahului?

    Many airlines fly to Kahului, the most common ones being Alaska 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 San Francisco $1,029, from Los Angeles $1,111, from Las Vegas $1,138
  • 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.
7.9
Alaska AirlinesOverall score based on 12478 reviews
8.5Crew
7.0Food
8.1Boarding
7.8Comfort
7.0Entertainment
Airline reviews

The flight attendant and first class were very friendly, efficient, and wanted to make sure that service was great. Highly recommend this airline.

10.0 ExcellentAnonymous, May 2026
SEA - LIH
Read more Alaska Airlines reviews

The flight attendant and first class were very friendly, efficient, and wanted to make sure that service was great. Highly recommend this airline.

Comfortable seats, good drinks with lots of water refills, staff was kind and understanding of my disabled mother!

The crew seem untrained and uncertain no one ever checked up on us in our first class cabin. I had to ask for water four times and the lady kept saying she was busy when they weren't really doing anything. Had to walk to the back of the plane to get water for myself. Crew seem new and unexperience. You can tell this by the fumbling they kept making trying to fight. (I miss Hawaiian air.)

Our meal order was screwed up. We had to choose from basic boxes. I was not happy.

You can standby to get on earlier flight if the seat is open.

Boarding was easy and quick. Staff was very friendly. Service of snacks and drinks by staff was outstanding.

Our flight when we finally got rerouted to a different destination than we were going was fine. But 2 days was taken out of our vacation because our flit was cancelled. We understand mechanical problems and of course don’t want to be on a plane that has mechanical problems.Wish there had been another solution.

Kayak wouldn’t refund me for a flight I was trying to cancel through Kayak. Alaska airlines said I had to cancel through Kayak. I called the customer service line and they couldn’t refund the flight that I booked through Kayak either. You stole my money. You will be hearing from my lawyer.

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

I behave had better flights this one was old and poor

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

Omg the disaster at the security was on another level! “Go to this end, sorry closed now, go to that end”. Ridiculous! This took over an hour! As far as the airline was concerned although I booked nearly a year ago I couldn’t get my bag tag - stand in another 15 minute line or my seat on Hawaiian Airlines- 5 more minutes! Then my TSA status was denied. Like what the heck! Makes a person not want to travel with this amount of incompetence

Fabulous if you have a portable wheelchair. They can store it in the galley and you can just walk out with it. Really nice and the flat seats are just incredible, very nice. iPads for movies, also pretty nice,

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

The crew at Hawaiian Airlines was fantastic. Kind and hard working. The pilots were great with giving us all the updates to make sure we were informed.

Very good. Nice plane and we sat in economy plus - bigger seats, more room. They served a meal and snacks, and the meal was an apple stuffed pancake that was very good! The snack for us was a hummus sandwich - also very good. The flight attendants were helpful and nice. They have plenty of movies and shows to watch. My only negative -- they changed our flights around and did not adjust the layovers, so we ended up with a very long and unnecessary layover in Honolulu.

Flight scheduled to take off at 5.55pm but it did not take off until 7pm due to some food delivery delay.

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.

Packed flight, which makes it tough on crew and boarding staff (and the customers of course). But this was great boarding, clear instructions, etc. Traveling on the weekends are always fraught with danger as you have families and less frequent flyers thus more confusion. But this flight went as planned.

Destroyed my suitcase. Tired of talking about it. Cancelling my unite mileage plus account.

Read the fine print. This was my flight home. I booked my flight for the quickest way home. Had a carry-on and a personal item. Same as my outbound flight. Apparently I needed to pre-pay extra for my carry-on. When I checked in, I was told that I had to check it. I said I’ll pay for it, and was told that this wasn’t an option anymore. They said I still had to pay $50 to check my carry-on. I told them I’ll pay whatever to just carry it in as intended. I was not allowed, so eventually I paid $50 to check my carry-on under a plane that was half full, with overhead compartments that were even less full. My white carry-on suitcase was practically destroyed getting from Idaho falls to Denver to Orange County. The low price air fair was a bait and switch. Got me to the gate, made me pay extra, then didn’t even allow me to pay for a carry on. Not to mention that I paid the $8 for WiFi that didn’t work. All to get my suitcase destroyed. I don’t think I’m going to even keep my Untied mileage plus membership and card. Apparently, membership does not have its privileges for this one.

The flight was delayed, they didn’t even have water for the toilets or for drinks

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

I flew from Santa Fe to Denver to catch a flight to London and the transfer of my luggage on arrival at Denver to the London flight worked perfectly. The crew on the ground and on board for the London flight were so friendly and efficient.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

Boarded early, left early, arrived 40 mins early! A win win for me!

New plane was lovely. Crew customer service is always lax but expected. Kraft on time and arrived safely.

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

Food is what you expect on a plane. Nothing gluten free. But that is expected. Drinks, apple juice, was fine. Seat, what I expected. Fine.

Everything went as planned. The only issue I had was with the gate C31 attendant. The person could barely speak English and was very difficult to understand.

The flight took off an hour late which made the connection concerning

Everything you need to know for your flight to Wailea