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Kailua

$184+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — HNL
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Portland to Kailua are usually found in September or January, booked 36 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$317
(Southwest)

One-way from

$184
(Alaska Airlines)

Popular in

December

Cheapest in

September

Average price

$478
Provider with most accurate pricing for Portland-Honolulu flight deals.
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Provider most trusted by Cheapflights users for Portland-Honolulu flights.
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From Portland to Kailua
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One-way flight from Portland to Kailua
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Highest demand for flights based on searches. 1% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 20, 2025.

This United Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 4/169:55 amPDX - HNL
2 stops13h 03mUnited Airlines
Wed 4/238:00 amHNL - PDX
2 stops13h 30mUnited Airlines
Deal found 2/19$312
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 3/65:15 amPDX - HNL
1 stop8h 40mSouthwest
Mon 3/108:40 amHNL - PDX
1 stop8h 20mSouthwest
Deal found 2/20$317
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/106:00 amPDX - HNL
1 stop9h 33mAmerican Airlines
Mon 3/109:32 pmHNL - PDX
1 stop10h 14mAmerican Airlines
Deal found 2/20$332
This Hawaiian Airlines deal was found by Cheapflights users on 2/19. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/156:07 pmPDX - HNL
Nonstop6h 21mHawaiian Airlines
Tue 4/225:15 pmHNL - PDX
1 stop8h 45mHawaiian Airlines
Deal found 2/19$333
This Delta deal was found by Cheapflights users on 2/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/285:10 amPDX - HNL
1 stop9h 01mDelta
Fri 5/212:40 pmHNL - PDX
1 stop8h 16mDelta
Deal found 2/18$347
This Alaska Airlines deal was found by Cheapflights users on 2/20. 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 3/138:59 pmPDX - HNL
1 stop27h 16mAlaska Airlines
Thu 3/208:26 pmHNL - PDX
Nonstop5h 39mAlaska Airlines
Deal found 2/20$401
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/132:33 pmPDX - HNL
3 stops33h 42mMultiple Airlines
Wed 3/197:45 amHNL - PDX
2 stops31h 10mMultiple Airlines
Deal found 2/19$489

Find flights from Portland to Kailua within your budget

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 February 20, 2025.

Fly from

Portland

Fly to

Kailua

Route

Depart

Return

Price

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Wed 4/16

9:55 am-7:58 pm

2 stops13h 03m

Honolulu

Wed 4/23

8:00 am-12:30 am

2 stops13h 30m

$312

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Thu 3/6

5:15 am-11:55 am

1 stop8h 40m

Honolulu

Mon 3/10

8:40 am-8:00 pm

1 stop8h 20m

$317

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Mon 3/10

6:00 am-12:33 pm

1 stop9h 33m

Honolulu

Mon 3/10

9:32 pm-10:46 am

1 stop10h 14m

$332

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Tue 4/15

6:07 pm-9:28 pm

Nonstop6h 21m

Honolulu

Tue 4/22

5:15 pm-5:00 am

1 stop8h 45m

$333

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Mon 4/28

5:10 am-11:11 am

1 stop9h 01m

Honolulu

Fri 5/2

12:40 pm-11:56 pm

1 stop8h 16m

$347

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Thu 3/13

8:59 pm-9:15 pm

1 stop27h 16m

Honolulu

Thu 3/20

8:26 pm-5:05 am

Nonstop5h 39m

$401

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Thu 3/13

2:33 pm-9:15 pm

3 stops33h 42m

Honolulu

Wed 3/19

7:45 am-5:55 pm

2 stops31h 10m

$489

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Sun 5/11

5:40 pm-8:44 pm

Nonstop6h 04m

$184

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Fri 3/7

5:15 am-11:55 am

1 stop8h 40m

$189

PortlandHonolulu

PDX - HNL

PDXHNL

Portland

Wed 2/26

9:55 am-9:23 pm

2 stops13h 28m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 13 results
1
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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.

Travel insights for flights from Portland to Kailua

Get recent, data-driven insights about flights from Portland to Kailua including ideal travel times, pricing trends, and more.

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 February 14, 2025.

The best time to book flights from Portland to Kailua is 36 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 February 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 February 16, 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 February 20, 2025.

The most flights from PDX to K4I are scheduled on a Monday (8 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (4 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 February 20, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Hawaiian Airlines
7.9
Good
2,317 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 7 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 35 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?

    $184 is the cheapest one-way deal found within the past few days, from Alaska Airlines. You may also be able to find cheap deals on Southwest and United Airlines, with prices starting from $189 and $194, respectively.

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

    Consider Fiji Airways (80%), Qantas Airways (80%) or Alaska Airlines (74%) 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 $164. On average you can expect to pay $1,269. The most popular route, (Portland - Honolulu), can usually be booked for $277.

  • 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.

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$225Average$320FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$383FlexibilityNo cancel feeOn-time69%
DeltaCheapest$227Average$526FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$250Average$421FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$316Average$549FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$339Average$538FlexibilityNo cancel feeOn-time85%
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