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Kailua

$169+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — HNL
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kailua are usually found in January or February, booked 90 days in advance, depart on a Wednesday or Thursday and return on a Saturday

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 October 29, 2025.

This United Airlines deal was found by Cheapflights users on 10/26. 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 12/27:30 amPDX - HNL
2 stops11h 55mUnited Airlines
Sat 12/68:00 amHNL - PDX
2 stops12h 52mUnited Airlines
Deal found 10/26$378
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/56:00 amPDX - HNL
2 stops13h 25mUnited Airlines
Mon 12/811:30 pmHNL - PDX
1 stop9h 33mUnited Airlines
Deal found 10/28$380
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/23:55 pmPDX - HNL
1 stop8h 35mUnited Airlines
Wed 12/178:00 amHNL - PDX
1 stop8h 41mUnited Airlines
Deal found 10/28$385
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 12/105:30 amPDX - HNL
1 stop9h 30mDelta
Mon 12/1511:23 pmHNL - PDX
1 stop9h 32mDelta
Deal found 10/28$386
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 12/44:32 pmPDX - HNL
1 stop9h 18mAlaska Airlines
Wed 12/109:50 pmHNL - PDX
Nonstop5h 35mAlaska Airlines
Deal found 10/28$389
This United Airlines deal was found by Cheapflights users on 10/26. 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.
Thu 12/43:55 pmPDX - HNL
1 stop8h 35mUnited Airlines
Mon 12/88:00 amHNL - PDX
2 stops12h 52mUnited Airlines
Deal found 10/26$392
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/26:00 amPDX - HNL
1 stop18h 02mAmerican Airlines
Wed 12/1011:00 pmHNL - PDX
1 stop9h 57mAmerican Airlines
Deal found 10/27$393
This Delta deal was found by Cheapflights users on 10/28. 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.
Sun 12/75:30 amPDX - HNL
1 stop9h 30mDelta
Wed 12/1711:23 pmHNL - PDX
1 stop9h 32mDelta
Deal found 10/28$395
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 12/910:18 amPDX - HNL
Nonstop6h 18mAlaska Airlines
Tue 12/166:33 pmHNL - PDX
1 stop9h 27mAlaska Airlines
Deal found 10/28$399
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 12/55:40 pmPDX - HNL
Nonstop6h 15mAlaska Airlines
Mon 12/812:05 pmHNL - PDX
1 stop19h 45mAlaska Airlines
Deal found 10/28$401

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 October 29, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$377
(KAYAK)

One-way from

$169
(United Airlines)

Popular in

June

Cheapest in

January

Average price

$567
Provider with most accurate pricing for Portland-Honolulu flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Honolulu flights.
Search Deals
From Portland to Kailua
Search Deals
One-way flight from Portland to Kailua
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 29, 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

Wed 1/14

2:38 pm-10:08 pm

1 stop9h 30m

Honolulu

Tue 1/20

11:59 pm-1:48 pm

1 stop11h 49m

$397

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Tue 12/9

10:10 am-9:03 pm

2 stops12h 53m

Honolulu

Mon 12/15

8:00 am-10:52 pm

2 stops12h 52m

$398

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Thu 1/15

5:40 pm-9:54 pm

Nonstop6h 14m

Honolulu

Thu 1/22

9:50 pm-5:33 am

Nonstop5h 43m

$398

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Thu 12/4

10:10 am-9:03 pm

2 stops12h 53m

Honolulu

Mon 12/8

8:00 am-10:52 pm

2 stops12h 52m

$398

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Fri 11/28

7:30 am-9:03 pm

2 stops15h 33m

Honolulu

Fri 12/5

11:30 pm-11:03 am

1 stop9h 33m

$402

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Wed 12/3

7:00 am-3:35 pm

2 stops10h 35m

Honolulu

Sun 12/7

9:50 pm-5:25 am

Nonstop5h 35m

$404

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Sat 1/17

7:45 am-9:08 pm

2 stops15h 23m

Honolulu

Sun 1/25

10:50 pm-12:33 pm

2 stops11h 43m

$408

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Sat 1/24

7:45 am-9:08 pm

2 stops15h 23m

Honolulu

Fri 1/30

10:50 pm-12:33 pm

2 stops11h 43m

$408

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Thu 12/4

10:36 am-11:50 pm

1 stop15h 14m

Honolulu

Mon 12/8

9:50 pm-5:25 am

Nonstop5h 35m

$417

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Wed 12/10

7:15 am-5:10 pm

1 stop11h 55m

Honolulu

Mon 12/15

9:50 pm-5:25 am

Nonstop5h 35m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 21 results
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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 October 24, 2025.

The best time to book flights from Portland to Kailua is 90 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, January is the cheapest month in which you can book a flight from Portland to Kailua (average of $235). Flying from Portland to Kailua in July is currently the most expensive (average of $523). 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 October 29, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 42% on flights from Portland to Kailua by exploring options for tickets at noon.

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 October 26, 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 October 29, 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
11,206 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,206 reviews
Alaska Airlines
8.0
Very good
11,206 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,240 reviews
Alaska Airlines
8.0
Very good
11,206 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,994 reviews
Alaska Airlines
8.0
Very good
11,206 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,794 reviews
Alaska Airlines
8.0
Very good
11,206 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
9,001 reviews
Alaska Airlines
8.0
Very good
11,206 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 3 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 41 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 9h 30m. The distance between Portland and Kailua is about 2601 mi. This flight may include one or multiple stops.

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

    Consider Korean Air (70%), 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 $226. On average you can expect to pay $633. The most popular route, (Portland - Honolulu), can usually be booked for $337.

  • 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, January is the cheapest month in which you can book a flight from Portland to Kailua (average of $235). Flying from Portland to Kailua in July is currently the most expensive (average of $523). 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

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Alternative routes for Portland to Kailua

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$173Average$405FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$219Average$379FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$271Average$391FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$277Average$480FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$379Average$602FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$385Average$581FlexibilityNo cancel feeOn-time85%

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