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Kailua

$161+ Cheap flights from Oakland, CA (OAK) to Kailua, HI

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — HNL
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Oakland to Kailua are usually found in January or September, booked 63 days in advance, depart on a Wednesday or Monday and return on a Wednesday

Cheap flight deals from Oakland to Kailua

Keep the following information in mind while searching for Oakland to Kailua flight deals. Data was last updated September 16, 2025.

Round-trip from

$346
(iWofly)

One-way from

$161
(KAYAK)

Popular in

June

Cheapest in

January

Average price

$402
From Oakland to Kailua
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One-way flight from Oakland to Kailua
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Highest demand for flights based on searches. 13% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Oakland to Kailua

Cheapest flights from Oakland to Kailua
Explore the most affordable flight options available from Oakland to Kailua. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This iWofly deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/149:45 amOAK - HNL
1 stop7h 41mHawaiian Airlines
Tue 10/219:17 amHNL - OAK
1 stop9h 08mHawaiian Airlines
Deal found 9/14$346
This Alaska Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:00 amOAK - HNL
1 stop7h 10mAlaska Airlines
Wed 10/2211:11 amHNL - OAK
Nonstop5h 19mAlaska Airlines
Deal found 9/15$347
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:11 amOAK - HNL
1 stop6h 57mMultiple Airlines
Tue 11/411:55 pmHNL - OAK
1 stop12h 00mMultiple Airlines
Deal found 9/15$348
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/272:49 pmOAK - HNL
1 stop9h 47mAlaska Airlines
Tue 11/411:53 amHNL - OAK
Nonstop5h 19mAlaska Airlines
Deal found 9/14$349
This Alaska Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/268:49 amOAK - HNL
Nonstop5h 33mAlaska Airlines
Mon 11/311:53 amHNL - OAK
Nonstop5h 19mAlaska Airlines
Deal found 9/15$350
This Alaska Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/207:00 amOAK - HNL
1 stop7h 10mAlaska Airlines
Tue 10/289:30 amHNL - OAK
1 stop9h 15mAlaska Airlines
Deal found 9/15$352
This Trip.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/310:00 amOAK - HNL
1 stop8h 59mAlaska Airlines
Mon 12/811:05 amHNL - OAK
1 stop7h 32mAlaska Airlines
Deal found 9/16$353
This Alaska Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:07 amOAK - HNL
1 stop7h 01mAlaska Airlines
Fri 11/711:53 amHNL - OAK
Nonstop5h 19mAlaska Airlines
Deal found 9/15$355
This KAYAK deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:45 amOAK - HNL
1 stop9h 23mAlaska Airlines
Thu 10/3010:53 amHNL - OAK
Nonstop5h 19mAlaska Airlines
Deal found 9/13$359
This Alaska Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3010:07 amOAK - HNL
1 stop8h 00mAlaska Airlines
Wed 11/510:27 amHNL - OAK
1 stop7h 53mAlaska Airlines
Deal found 9/15$360
This Alaska Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/42:49 pmOAK - HNL
1 stop9h 47mAlaska Airlines
Tue 11/119:55 pmHNL - OAK
1 stop10h 30mAlaska Airlines
Deal found 9/15$361

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Kailua that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Oakland to Kailua that are best for you.

Fly from

Oakland

Fly to

Kailua

Route

Depart

Return

Price

OaklandHonolulu

OAK - HNL

OAKHNL

Oakland

Mon 2/2

8:30 am-12:15 pm

Nonstop5h 45m

Honolulu

Wed 2/4

10:33 am-8:35 pm

1 stop8h 02m

$347

OaklandHonolulu

OAK - HNL

OAKHNL

Oakland

Mon 10/27

8:35 am-11:08 am

Nonstop5h 33m

Honolulu

Mon 11/3

11:53 am-7:12 pm

Nonstop5h 19m

$350

OaklandHonolulu

OAK - HNL

OAKHNL

Oakland

Thu 1/29

8:30 am-12:15 pm

Nonstop5h 45m

Honolulu

Wed 2/4

6:15 am-8:35 pm

1 stop12h 20m

$355

OaklandHonolulu

OAK - HNL

OAKHNL

Oakland

Mon 11/17

2:49 pm-10:36 pm

1 stop9h 47m

Honolulu

Tue 11/25

5:36 am-9:28 pm

1 stop13h 52m

$357

OaklandHonolulu

OAK - HNL

OAKHNL

Oakland

Mon 1/26

8:00 am-3:05 pm

1 stop9h 05m

Honolulu

Thu 1/29

10:33 am-8:35 pm

1 stop8h 02m

$357

OaklandHonolulu

OAK - HNL

OAKHNL

Oakland

Wed 1/7

10:10 am-7:45 pm

1 stop11h 35m

Honolulu

Mon 1/12

9:40 pm-9:08 am

1 stop9h 28m

$369

OaklandHonolulu

OAK - HNL

OAKHNL

Oakland

Sun 12/7

8:45 am-12:24 pm

Nonstop5h 39m

Honolulu

Tue 12/9

12:27 pm-7:39 pm

Nonstop5h 12m

$370

OaklandHonolulu

OAK - HNL

OAKHNL

Oakland

Thu 10/23

2:33 pm-11:59 pm

1 stop12h 26m

Honolulu

Mon 10/27

9:38 am-8:21 pm

1 stop7h 43m

$373

OaklandHonolulu

OAK - HNL

OAKHNL

Oakland

Sun 10/19

7:30 am-9:59 am

Nonstop5h 29m

Honolulu

Fri 10/24

8:10 am-9:25 pm

1 stop10h 15m

$375

OaklandHonolulu

OAK - HNL

OAKHNL

Oakland

Mon 12/8

10:00 am-4:19 pm

1 stop8h 19m

Honolulu

Fri 12/12

12:27 pm-7:39 pm

Nonstop5h 12m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 20 results
1
2

Best time to book a flight from Oakland to Kailua

Have a flexible travel schedule? Discover the best time to fly to Kailua from Oakland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Oakland to Kailua

How far ahead should I book a flight from Oakland, California to Kailua?

Use this chart to determine the optimal time to book a round-trip flight from Oakland to Kailua. Price data was last updated on September 12, 2025.

Booking 63 days in advance of your planned departure date is, on average, the best time to get cheap flights from Oakland, California to Kailua. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Oakland, California to Kailua?

Currently, November is the cheapest month in which you can book a flight from Oakland, California to Kailua (average of $469). Flying from Oakland, California to Kailua in June is currently the most expensive (average of $687). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OAK to K4I?

Find hourly flight availability from Oakland to Kailua. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Oakland, California to Kailua, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Oakland, California to Kailua

Explore weekly flight availability from Oakland to Kailua. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 16, 2025.

The most flights from OAK to K4I are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

Reviews of airlines servicing Kailua

Get insights into the airlines that provide service to Kailua. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kailua. Reviews last updated September 16, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Hawaiian Airlines from Oakland to Kailua have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Hawaiian Airlines
7.8
Good
2,724 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,924 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Kailua. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Oakland to Kailua?

    Located just 7.0 mi from the city center, Oakland is the airport most travelers will use when flying to Kailua from Oakland. Booking flights from Oakland (OAK) to Kailua should be relatively easy as there are 4 daily outbound flights to Kailua from 4 different airlines.

  • How popular is this Oakland, California to Kailua flight route?

    The Oakland to Kailua flight path was viewed by 22 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Oakland, California to Kailua?

    Departing from Oakland, California to Kailua will take you 5h 45m. Oakland, California and Kailua are separated by a distance of 2405 mi. Generally, flights for this route are nonstop.

  • What are the most reliable airlines from Oakland, California to Kailua?

    No one likes to see their flight delayed. When booking a flight from Oakland, California to Kailua consider choosing Southwest (93%), Alaska Airlines (84%) or Hawaiian Airlines (84%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Oakland, California to Kailua?

    The cheapest flight price from Oakland, California to Kailua is $127. On average you can expect to pay $965. The most popular route, (Oakland - Honolulu), can usually be booked for $326.

  • Can I find deals for flights from Oakland to Kailua that include hotel bookings?

    Yes. In addition to deals on Oakland to Kailua flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Kailua?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Kailua.

  • Can I find deals for business class flights from Oakland to Kailua?

    Yes. Cheapflights offers flight deals from Oakland to Kailua by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oakland, California to Kailua?

    Currently, November is the cheapest month in which you can book a flight from Oakland, California to Kailua (average of $469). Flying from Oakland, California to Kailua in June is currently the most expensive (average of $687). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Oakland to Kailua

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Oakland to Kailua

Discover the top 4 airlines that operate flights from Oakland to Kailua. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$180Average$557FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$258Average$448FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$266Average$475FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$287Average$539FlexibilityNo cancel feeOn-time63%

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