$129 Cheap flight deals from Portland (PDX) to Kailua (HNL)

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This Weekend's Flight Deals from Portland to Kailua

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Dec 28 - Wed, Feb 4
PDX
Portland Intl.
HNL
Daniel K. Inouye Intl.
$683 Roundtrip, found 5 hours ago
$683
Roundtrip
found 5 hours ago
Select Alaska Airlines flight, departing Sun, Dec 28 from Portland Intl. to Daniel K. Inouye Intl., returning Wed, Feb 4, priced at $683 found 5 hours ago

Airfares from $129 One Way, $257 Round Trip from Portland to Kailua

Prices starting at $257 for return flights and $129 for one-way flights to Kailua were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Mar 4 - Wed, Mar 11
PDX
Portland
HNL
Oahu
$257 Roundtrip, found 5 days ago
$257
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Mar 4 from Portland to Oahu, returning Wed, Mar 11, priced at $257 found 5 days ago
Wed, Jan 21 - Mon, Jan 26
PDX
Portland
HNL
Oahu
$263 Roundtrip, found 5 days ago
$263
Roundtrip
found 5 days ago
Select United flight, departing Wed, Jan 21 from Portland to Oahu, returning Mon, Jan 26, priced at $263 found 5 days ago
Wed, Jan 28 - Thu, Jan 29
PDX
Portland
HNL
Oahu
$268 Roundtrip, found 3 days ago
$268
Roundtrip
found 3 days ago
Select United flight, departing Wed, Jan 28 from Portland to Oahu, returning Thu, Jan 29, priced at $268 found 3 days ago
Sun, Jan 18 - Sun, Jan 25
PDX
Portland
HNL
Oahu
$302 Roundtrip, found 8 hours ago
$302
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Sun, Jan 18 from Portland to Oahu, returning Sun, Jan 25, priced at $302 found 8 hours ago
Wed, Feb 4 - Mon, Feb 9
PDX
Portland
HNL
Oahu
$316 Roundtrip, found 1 hour ago
$316
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Feb 4 from Portland to Oahu, returning Mon, Feb 9, priced at $316 found 1 hour ago

Kailua economy flight packages

Price found within the past 48 hours. Click for updated prices.
Paradise Bay Resort
3.5-star property

Paradise Bay Resort

8.8/10 Excellent! (1,002 reviews)

Feb 2 - Feb 4

2 night stay

Portland (PDX) to Honolulu (HNL)

United • Non-stop roundtrip • Coach
Price was $709, price is now $494 per person
$494
per person
found 1 day ago
This is a quiet little gem. Off the tourist path and scenery is spectacular. Enjoyed listening to Uncle Danny kanikapila. Tea, banana bread and coffee were yummy. Driveway, parking and stairs are a bit intimidating but just go slow. It is worth it. Am afraid to tell others about this wonderful place because I don’t want it to change. I will come again.

Reviewed on Nov 2, 2025

Sheraton Waikiki Beach Resort
4.5-star property

Sheraton Waikiki Beach Resort

9.2/10 Wonderful! (2,732 reviews)

Feb 2 - Feb 4

2 night stay

Portland (PDX) to Honolulu (HNL)

United • Non-stop roundtrip • Coach
Price was $903, price is now $625 per person
$625
per person
found 1 day ago
When we got into our family room, and I crawled into my bed it was wet. The sheets were wet with urine from a previous guest before us. The urine had even soaked into the mattress there was so much. I called housekeeping and after 20 minutes I called again because nobody responded. What was most upsetting was that the general manger on duty the next day was not apologizing and saying sorry, he offered to give us a 200.00 food credit. Our family has never been to Hawaii and we paid a lot of money to stay at this beautiful hotel. I expected more from the management and was extremely disappointed in how they tried to compensate for a gross error in preparing our room. If the manager would have said, he was very sorry and offered to upgrade our room or even offer to cover one of our four nights that would have been respectable service. He did end up giving us a food credit equal to one night, but I had to almost beg and plead with him.

Reviewed on Dec 6, 2025

The Royal Hawaiian, a Luxury Collection Resort, Waikiki
5.0-star property

The Royal Hawaiian, a Luxury Collection Resort, Waikiki

9.2/10 Wonderful! (1,004 reviews)

Feb 2 - Feb 4

2 night stay

Portland (PDX) to Honolulu (HNL)

United • Non-stop roundtrip • Coach
Price was $903, price is now $628 per person
$628
per person
found 1 day ago
We really enjoyed our stay at this iconic hotel. The staff and service was world class. There are so many different restaurants within easy walking distance and the beach access was super easy. The pool area was a favorite for our 7 year old, as well as the koi pond and the daily feeding experience. A very enjoyable stay for sure.

Reviewed on Oct 20, 2025

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More About Flying To Kailua from Portland

Route Information for Flights from Portland to Kailua

Origin Airport IATA Code
PDX
Destination Airport IATA Code
HNL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Portland to Kailua

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.