HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kailua

$239+ Cheap flights from Portland (PDX) 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — HNL
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Kailua with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Portland to Kailua are usually found in January or September, booked 82 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap flight deals from Portland to Kailua

Keep the following information in mind while searching for Portland to Kailua flight deals. Data was last updated June 12, 2025.

Round-trip from

$443
(United Airlines)

One-way from

$239
(American Airlines)

Popular in

June

Cheapest in

January

Average price

$651
From Portland to Kailua
Search Deals
One-way flight from Portland to Kailua
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

Find flight deals from Portland to Kailua

Cheapest flights from Portland to Kailua
Explore the most affordable flight options available from Portland to Kailua. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/71:45 pmPDX - HNL
1 stop7h 48mUnited Airlines
Sun 9/211:30 pmHNL - PDX
1 stop8h 15mUnited Airlines
Deal found 6/9$443
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/157:55 pmPDX - HNL
1 stop18h 20mDelta
Tue 9/308:55 pmHNL - PDX
1 stop10h 29mDelta
Deal found 6/10$446
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/185:05 amPDX - HNL
1 stop10h 17mAmerican Airlines
Sun 8/249:11 pmHNL - PDX
1 stop10h 33mAmerican Airlines
Deal found 6/10$447
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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 9/167:21 amPDX - HNL
1 stop16h 10mAlaska Airlines
Mon 9/298:43 pmHNL - PDX
1 stop9h 42mAlaska Airlines
Deal found 6/10$448
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2710:55 amPDX - HNL
1 stop8h 10mSouthwest
Wed 9/38:15 amHNL - PDX
1 stop8h 35mSouthwest
Deal found 6/9$455
This Hawaiian Airlines deal was found by Cheapflights users on 6/12. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/75:40 pmPDX - HNL
1 stop8h 54mHawaiian Airlines
Wed 8/136:00 pmHNL - PDX
1 stop9h 00mHawaiian Airlines
Deal found 6/12$502

Cheapflights Fare Finder

Customize your flight search to find flights from Portland 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 June 12, 2025.
Use the filters below to find and compare flights from Portland to Kailua that are best for you.

Fly from

Portland

Fly to

Kailua

Route

Depart

Return

Price

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Sun 9/7

1:45 pm-6:33 pm

1 stop7h 48m

Honolulu

Sun 9/21

1:30 pm-12:45 am

1 stop8h 15m

$443

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Mon 9/15

7:55 pm-11:15 am

1 stop18h 20m

Honolulu

Tue 9/30

8:55 pm-10:24 am

1 stop10h 29m

$446

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Mon 8/18

5:05 am-12:22 pm

1 stop10h 17m

Honolulu

Sun 8/24

9:11 pm-10:44 am

1 stop10h 33m

$447

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Tue 9/16

7:21 am-8:31 pm

1 stop16h 10m

Honolulu

Mon 9/29

8:43 pm-9:25 am

1 stop9h 42m

$448

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Wed 8/27

10:55 am-4:05 pm

1 stop8h 10m

Honolulu

Wed 9/3

8:15 am-7:50 pm

1 stop8h 35m

$455

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Thu 8/7

5:40 pm-11:34 pm

1 stop8h 54m

Honolulu

Wed 8/13

6:00 pm-6:00 am

1 stop9h 00m

$502

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Sat 8/30

2:56 pm-9:34 pm

1 stop9h 38m

$239

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Sun 8/17

1:23 pm-8:30 pm

1 stop10h 07m

$252

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Sat 9/27

11:05 am-4:18 pm

1 stop8h 13m

$255

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Sun 8/31

7:01 am-8:31 pm

2 stops16h 30m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 13 results
1
2

Best time to book a flight from Portland to Kailua

Have a flexible travel schedule? Discover the best time to fly to Kailua from Portland 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 Portland to Kailua

How far ahead should I book a flight from Portland to Kailua?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Kailua. Price data was last updated on June 9, 2025.

The best time to book flights from Portland to Kailua is 82 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Portland to Kailua?

Currently, November is the cheapest month in which you can book a flight from Portland to Kailua (average of $469). Flying from Portland 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 PDX to K4I?

Find hourly flight availability from Portland 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 June 12, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland to Kailua as you normally would.

What is the cheapest day to fly from Portland to Kailua?

Use this chart to determine the cheapest time to fly round-trip from Portland to Kailua. Price data was last updated on June 8, 2025.

Travelers seeking maximum savings on their Portland to Kailua flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Portland to Kailua

Explore weekly flight availability from Portland 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 June 12, 2025.

The most flights from PDX to K4I are scheduled on a Thursday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Kailua by month

Plan your trip to Kailua by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kailua ranges from 0.3 - 3.2 inches per month. December is typically the wettest month, when rainfall can reach 3.2 in. June is typically the driest time to visit Kailua when rainfall is around 0.3 in.

Temperature in Kailua by month

Plan your trip to Kailua by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kailua, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 73.4 F).

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 June 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Portland to Kailua by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Portland 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 Portland to Kailua?

    Most people fly from Portland (PDX) if they book a flight from Portland to Kailua. On average, Portland has 2 outbound flights to Kailua per day from 6 airlines. Portland is conveniently located just 6.0 mi from Portland’s city center.

  • How popular is this Portland to Kailua flight route?

    The Portland to Kailua flight path was viewed by 24 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • What are the cheapest airlines to fly from Portland to Kailua one-way?

    $239 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Hawaiian Airlines and United Airlines, with prices starting from $252 and $260, respectively.

  • What are the most reliable airlines from Portland to Kailua?

    Consider Korean Air (92%), Alaska Airlines (86%) or Hawaiian Airlines (86%) when booking your flight. These represent the most reliable airlines when flying from Portland to Kailua.

  • What are the cheapest flights from Portland to Kailua?

    The cheapest flight price from Portland to Kailua is $284. On average you can expect to pay $2,234. The most popular route, (Portland - Honolulu), can usually be booked for $404.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland 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 Portland to Kailua?

    Currently, November is the cheapest month in which you can book a flight from Portland to Kailua (average of $469). Flying from Portland 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Kailua

See prices for flight routes from nearby airports that may be better suited for you.
Portland to Honolulu flights
Portland to Kahului flights
Portland to Kailua-Kona flights
Portland to Lihue flights
Boise to Honolulu flights
Boise to Lihue flights
Eugene to Honolulu flights
Boise to Kahului flights
Eugene to Kahului flights
Boise to Kailua-Kona flights
Medford to Honolulu flights
Redmond to Kahului flights
Redmond to Honolulu flights
Redmond to Lihue flights
Medford to Kahului flights
Eugene to Kailua-Kona flights
Portland to Hilo flights
Redmond to Kailua-Kona flights
Medford to Kailua-Kona flights
Eugene to Lihue flights
Yakima to Honolulu flights
Medford to Lihue flights
Portland to Kapalua flights
Boise to Hilo flights
Medford to Hilo flights
Redmond to Kapalua flights
Pendleton to Honolulu flights
Eugene to Hilo flights
Yakima to Lihue flights
Portland to Waimea (Big Island) flights
Portland to Hoolehua flights
Portland to Hana flights
North Bend to Kahului flights
Eugene to Kapalua flights
Portland to Lanai City flights
Medford to Kapalua flights
Boise to Kapalua flights
Boise to Hana flights

Top 6 airlines flying from Portland to Kailua

Discover the top 6 airlines that operate flights from Portland 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$175Average$433FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$210Average$369FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$230Average$333FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$267Average$483FlexibilityNo cancel feeOn-time63%
Hawaiian AirlinesCheapest$376Average$561FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$379Average$580FlexibilityNo cancel feeOn-time75%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.