$149 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 5/18. 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
$296
Typical prices: $554-$370
Alaska Airlines
Mon 5/11Tue 5/19
OAK - OGG • Non-stop
Cheapest one-way
$149
Typical prices: $142-$329
Alaska Airlines
Mon 5/18
SAN - 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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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

Mon, May 11 - Tue, May 19
Alaska Airlines Logo
7:09 am - 9:25 am
OAK
-
OGG
5h 16mnonstop
Alaska Airlines Logo
1:08 pm - 9:15 pm
OGG
-
OAK
5h 07mnonstop
$296Alaska Airlines
Mon, May 11 - Tue, May 19
Alaska Airlines Logo
7:13 am - 9:32 am
SJC
-
OGG
5h 19mnonstop
Alaska Airlines Logo
1:20 pm - 9:24 pm
OGG
-
SJC
5h 04mnonstop
$296Alaska Airlines
Mon, May 25 - Thu, Jun 4
Alaska Airlines Logo
6:30 pm - 9:30 pm
SAN
-
OGG
6h 00mnonstop
Alaska Airlines Logo
10:30 pm - 6:58 am
OGG
-
SAN
5h 28mnonstop
$297Alaska Airlines
Mon, May 25 - Mon, Jun 1
Alaska Airlines Logo
6:30 pm - 9:30 pm
SAN
-
OGG
6h 00mnonstop
Alaska Airlines Logo
12:29 pm - 8:59 pm
OGG
-
SAN
5h 30mnonstop
$307Alaska Airlines
Thu, May 28 - Thu, May 28
Delta Logo
11:00 am - 5:48 pm
SAN
-
OGG
9h 48m
1 stop
Delta Logo
10:00 pm - 10:19 am
OGG
-
SAN
9h 19m
1 stop
$311Delta
Thu, May 14 - Thu, May 21
Delta Logo
3:15 pm - 7:35 pm
SAN
-
OGG
7h 20m
1 stop
Delta Logo
10:00 pm - 10:19 am
OGG
-
SAN
9h 19m
1 stop
$316Delta
Thu, May 28 - Tue, Jun 2
United Airlines Logo
6:52 pm - 9:26 pm
SFO
-
OGG
5h 34mnonstop
United Airlines Logo
12:00 pm - 7:59 pm
OGG
-
SFO
4h 59mnonstop
$317United Airlines
Mon, May 11 - Thu, May 14
United Airlines Logo
10:55 am - 7:26 pm
SAN
-
OGG
11h 31m
2 stops
United Airlines Logo
1:10 pm - 11:59 pm
OGG
-
SAN
7h 49m
1 stop
$322United Airlines
Tue, May 12 - Tue, May 19
Southwest Logo
8:55 am - 4:05 pm
DEN
-
OGG
11h 10m
1 stop
Southwest Logo
8:35 pm - 9:55 am
OGG
-
DEN
9h 20m
1 stop
$380Southwest
Wed, Aug 26 - Mon, Aug 31
Southwest Logo
7:30 am - 1:45 pm
DEN
-
OGG
10h 15m
1 stop
Southwest Logo
8:25 pm - 10:05 am
OGG
-
DEN
9h 40m
1 stop
$407Southwest
Useful Info

Good to know - Book Cheap Wailea Plane Tickets

Low seasonJanuary
Cheapest flight$149
Best time to beat the crowds with an average 17% 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 
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 Oakland5h 10m
    Flights from San Diego5h 44m
    Flights from San Francisco5h 16m
    Flights from San Jose5h 10m
    Flights from Los Angeles5h 29m
  • 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 $296 return. The most popular connection is from Los Angeles to Kahului and KAYAK users have found round-trip deals for as low as $321 in the last 3 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 $854, from Las Vegas $932, from Los Angeles $939
  • 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 12275 reviews
7.8Comfort
7.0Food
8.5Crew
7.0Entertainment
8.1Boarding
Airline reviews

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

10.0 ExcellentYibin, Apr 2026
OGG - HNL
Read more Alaska Airlines reviews

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

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

Short trip from Honolulu to Kauai. Not a major issue. Only concern was the drop off of the luggage for departure. Only one person handling all of the passengers. She was busting her butt.

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.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

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.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

The flight crew on this leg of my trip was very friendly and pleasant. Every one of them was humorous, as well as helpful and accommodating. This group was BY FAR the best crew I’ve flown with. They deserve kudos.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was delayed from take off because only one runway was operational in San Francisco.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Really hard landing... as in slammed into the runway then hit the brakes really hard ...

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

My bags were misplaced!!! Im in a foreign country with no bags

The entertainment options on the seat back video boards were nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

The staff was nice. I appreciated that I was able to take an earlier flight, even though it was last minute. The boarding process felt rather chaotic.

Overall a good experience, however Wifi was not working on the flight.

Airlines should be prohibited from using the seats they get away with.

My flight got delayed a total of five times. And the boarding gate changed four times. most of the time the platform was not up-to-date with the changes taking place. The most discouraging part of the entire trip by far.

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

American delayed the flight for a crew rest period. The delay occurred late in the evening - the earliest i can find is 10:20 pm. With a 6 am flight anyone on the flight would have already have been asleep (unless you are insane, a vampire or on drugs) and at least for me i was already on the way to the airport at 445 am the next morning when i discovered they delayed the flight until 9 am. Given the incoming flight was in the air at 6 pm the evening before this should have been figured out a lot more timely that was there only crew to use. Just frustrating given there is no consideration for customer experience anymore in flying.

Returned home with a blood clot from flight homes and the uncomfortable aircraft I was on.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

The crew was very kind, but no in-flight entertainment monitors and a 2 hour and 30 minute delay was extremely frustrating.

Everything was delayed and the staff sent me to the wrong gate, causing me to miss one of my flights. I arrived at my destination 6 hours later than I was supposed to.

Everything you need to know for your flight to Wailea