HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kailua

$174+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — HNL
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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 February, 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 August 20, 2025.

Round-trip from

$372
(United Airlines)

One-way from

$174
(Southwest)

Popular in

December

Cheapest in

January

Average price

$567
From Portland to Kailua
Search Deals
One-way flight from Portland to Kailua
Search Deals
High demand for flights, 0% potential price rise
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 August 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 August 20, 2025.

This United Airlines deal was found by Cheapflights users on 8/19. 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.
Tue 9/167:45 amPDX - HNL
1 stop11h 20mUnited Airlines
Tue 9/231:30 pmHNL - PDX
1 stop8h 15mUnited Airlines
Deal found 8/19$372
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Wed 9/171:45 pmPDX - HNL
1 stop7h 48mUnited Airlines
Wed 9/241:30 pmHNL - PDX
1 stop8h 15mUnited Airlines
Deal found 8/17$373
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Tue 9/167:45 amPDX - HNL
2 stops15h 04mUnited Airlines
Tue 9/307:00 amHNL - PDX
1 stop10h 50mUnited Airlines
Deal found 8/19$378
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Sun 10/262:45 pmPDX - HNL
1 stop9h 38mAmerican Airlines
Sun 11/211:00 pmHNL - PDX
1 stop9h 58mAmerican Airlines
Deal found 8/18$382
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 9/121:45 pmPDX - HNL
1 stop7h 48mUnited Airlines
Tue 9/1611:10 amHNL - PDX
2 stops10h 35mUnited Airlines
Deal found 8/19$387
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Tue 9/95:30 amPDX - HNL
2 stops13h 59mUnited Airlines
Tue 9/99:40 pmHNL - PDX
2 stops12h 03mUnited Airlines
Deal found 8/19$388
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Tue 10/287:45 amPDX - HNL
1 stop9h 08mAmerican Airlines
Thu 11/1311:00 pmHNL - PDX
1 stop9h 58mAmerican Airlines
Deal found 8/19$389
This Southwest deal was found by Cheapflights users on 8/18. 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.
Mon 11/106:10 amPDX - HNL
1 stop9h 00mSouthwest
Thu 11/138:15 amHNL - PDX
1 stop13h 20mSouthwest
Deal found 8/18$392

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 August 20, 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

Tue 9/16

7:45 am-4:05 pm

1 stop11h 20m

Honolulu

Tue 9/23

1:30 pm-12:45 am

1 stop8h 15m

$372

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Wed 9/17

1:45 pm-6:33 pm

1 stop7h 48m

Honolulu

Wed 9/24

1:30 pm-12:45 am

1 stop8h 15m

$373

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Tue 10/28

7:45 am-1:53 pm

1 stop9h 08m

Honolulu

Thu 11/13

11:00 pm-10:58 am

1 stop9h 58m

$389

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Wed 10/22

6:45 am-12:50 pm

1 stop9h 05m

Honolulu

Wed 10/29

8:15 am-7:40 pm

1 stop8h 25m

$392

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Wed 10/8

6:45 am-12:50 pm

1 stop9h 05m

Honolulu

Wed 10/15

8:15 am-7:40 pm

1 stop8h 25m

$392

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Sun 11/16

5:10 am-1:45 pm

1 stop10h 35m

Honolulu

Thu 11/20

10:05 am-7:55 pm

1 stop7h 50m

$392

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Thu 10/23

6:30 am-12:50 pm

1 stop9h 20m

Honolulu

Fri 10/31

9:00 pm-12:30 pm

1 stop12h 30m

$392

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Mon 11/10

6:10 am-1:10 pm

1 stop9h 00m

Honolulu

Thu 11/13

9:00 pm-9:15 am

1 stop10h 15m

$392

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Tue 9/9

7:10 am-4:25 pm

1 stop12h 15m

Honolulu

Tue 9/9

9:00 pm-11:05 am

1 stop11h 05m

$392

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Tue 10/7

6:45 am-12:50 pm

1 stop9h 05m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 18 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 August 8, 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 August 20, 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 August 17, 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.

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 August 20, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Portland to Kailua to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Delta
8.0
Very good
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Hawaiian Airlines
7.8
Good
2,668 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
United Airlines
7.4
Good
8,928 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.

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 33 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 Portland to Kailua?

    Departing from Portland to Kailua will take you 11h 20m. The distance between Portland and Kailua is about 2601 mi.

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

    $174 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $174 and $174, respectively.

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

    Consider Korean Air (66%), Alaska Airlines (59%) or Hawaiian Airlines (59%) 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 $234. On average you can expect to pay $1,004. The most popular route, (Portland - Honolulu), can usually be booked for $347.

  • 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 Kahului flights
Boise to Lihue flights
Medford to Honolulu flights
Redmond to Kailua-Kona flights
Eugene to Kailua-Kona flights
Portland to Hilo flights
Boise to Kailua-Kona flights
Medford to Lihue flights
Eugene to Kahului flights
Eugene to Honolulu flights
Eugene to Lihue flights
Redmond to Kahului flights
Medford to Kahului flights
Redmond to Honolulu flights
Medford to Kailua-Kona flights
Redmond to Lihue flights
Boise to Hilo flights
Yakima to Honolulu flights
Portland to Kapalua flights
Eugene to Hilo flights
Portland to Hoolehua flights
Boise to Hana flights
Medford to Hilo flights
Portland to Waimea (Big Island) flights
Pendleton to Honolulu flights
Redmond to Kapalua flights
Eugene to Kapalua flights
North Bend to Kahului flights
Boise to Kapalua flights
Yakima to Lihue flights
Portland to Hana flights
Portland to Lanai City flights
Medford to Kapalua 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$173Average$415FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$213Average$368FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$247Average$367FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$267Average$475FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$378Average$594FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$383Average$574FlexibilityNo cancel feeOn-time85%

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.