$162 Cheap flight deals from Portland (PDX) to South Maui (OGG)

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This Weekend's Flight Deals from Portland to South Maui

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.

Fri, Sep 18 - Fri, Sep 25
PDX
Portland Intl.
OGG
Kahului
$999 Roundtrip, found 3 hours ago
$999
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Fri, Sep 18 from Portland Intl. to Kahului, returning Fri, Sep 25, priced at $999 found 3 hours ago

Airfares from $162 One Way, $325 Round Trip from Portland to South Maui

Prices starting at $325 for return flights and $162 for one-way flights to South Maui were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Nov 2 - Tue, Nov 10
PDX
Portland
OGG
Maui
$325 Roundtrip, found 1 day ago
$325
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Nov 2 from Portland to Maui, returning Tue, Nov 10, priced at $325 found 1 day ago
Tue, Nov 10 - Tue, Nov 17
PDX
Portland
OGG
Maui
$339 Roundtrip, found 4 days ago
$339
Roundtrip
found 4 days ago
Select United flight, departing Tue, Nov 10 from Portland to Maui, returning Tue, Nov 17, priced at $339 found 4 days ago
Tue, Oct 6 - Wed, Oct 14
PDX
Portland
OGG
Maui
$345 Roundtrip, found 6 days ago
$345
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Oct 6 from Portland to Maui, returning Wed, Oct 14, priced at $345 found 6 days ago
Fri, Jan 8 - Fri, Jan 29
PDX
Portland
OGG
Maui
$346 Roundtrip, found 6 days ago
$346
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Fri, Jan 8 from Portland to Maui, returning Fri, Jan 29, priced at $346 found 6 days ago
Mon, Nov 2 - Tue, Nov 10
PDX
Portland
OGG
Maui
$360 Roundtrip, found 1 day ago
$360
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Nov 2 from Portland to Maui, returning Tue, Nov 10, priced at $360 found 1 day ago

South Maui economy flight packages

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

Maui Schooner Resort

9.4/10 Exceptional! (566 reviews)

Nov 1 - Nov 7

6 night stay

Portland (PDX) to Kahului (OGG)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,610, price is now $1,148 per person
$1,148
per person
found 1 day ago
Cool

Reviewed on Sep 10, 2026

Maui Beach Vacation Club
2.5-star property

Maui Beach Vacation Club

8.4/10 Very Good! (937 reviews)

Oct 18 - Oct 24

6 night stay

Portland (PDX) to Kahului (OGG)

Southwest Airlines • Coach

Kahului (OGG) to Portland (PDX)

Alaska Airlines • Coach
Save 100% on your flight
Price was $2,068, price is now $1,179 per person
$1,179
per person
found 1 day ago
The building was right at the street. Too much driving car noise. There was no house keeping available. Across street was the beach but not appropriate for swimming

Reviewed on Sep 11, 2026

Hotel Wailea, Relais & Chateaux - Adults Only
5.0-star property

Hotel Wailea, Relais & Chateaux - Adults Only

9.4/10 Exceptional! (1,000 reviews)

Nov 1 - Nov 7

6 night stay

Portland (PDX) to Kahului (OGG)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $7,025, price is now $4,241 per person
$4,241
per person
found 1 day ago
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards! Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches. The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool! The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X

Reviewed on Sep 6, 2026

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More About Flying To South Maui from Portland

Route Information for Flights from Portland to South Maui

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

Portland to South Maui

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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.