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Hilton Head Island

$429+ Cheap flights from Portland to Hilton Head Island (PDX - HHH)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — HHH
May 27 — Jun 31
Wed 5/27
Wed 6/3
1 adult, Economy
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Cheap flight deals from Portland to Hilton Head Island

Cheapest flights from Portland to Hilton Head Island
Explore the most affordable flight options available from Portland to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 27, 2026.

This Delta deal was found by Cheapflights users on 4/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:55 pm
PDX
-
HHH
2 stops13h 24m
Delta
Wed 10/2812:00 pm
HHH
-
PDX
2 stops14h 52m
Delta
Deal found 4/26$429
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Fri 10/2310:44 pm
PDX
-
HHH
1 stop8h 29m
American Airlines
Wed 10/283:58 pm
HHH
-
PDX
1 stop7h 28m
American Airlines
Deal found 4/23$479
This American Airlines deal was found by Cheapflights users on 4/24. 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 5/511:23 pm
PDX
-
HHH
1 stop10h 14m
American Airlines
Tue 5/122:54 pm
HHH
-
PDX
1 stop8h 25m
American Airlines
Deal found 4/24$497
This American Airlines deal was found by Cheapflights users on 4/24. 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 5/245:49 am
PDX
-
HHH
1 stop7h 43m
American Airlines
Sun 5/312:03 pm
HHH
-
PDX
1 stop10h 48m
American Airlines
Deal found 4/24$546
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Mon 5/1111:55 pm
PDX
-
HHH
2 stops12h 46m
United Airlines
Fri 5/153:08 pm
HHH
-
PDX
1 stop10h 27m
United Airlines
Deal found 4/24$704

Find flight deals from Portland to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Hilton Head Island (HHH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$429
(Delta)
Provider with most accurate pricing for Portland-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Hilton Head Island flights.
Search Deals
From Portland to Hilton Head Island
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Hilton Head Island 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 April 27, 2026.
Use the filters below to find and compare flights from Portland to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Sun 5/24

5:49 am-4:32 pm

1 stop7h 43m

Hilton Head Island

Sun 5/31

2:03 pm-9:51 pm

1 stop10h 48m

$546

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Mon 5/11

11:55 pm-3:41 pm

2 stops12h 46m

Hilton Head Island

Fri 5/15

3:08 pm-10:35 pm

1 stop10h 27m

$704
Quickest round-trip

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Mon 5/11

10:23 pm-10:47 am

1 stop9h 24m

Hilton Head Island

Fri 5/15

2:58 pm-9:03 pm

1 stop9h 05m

$918

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Sun 5/24

6:46 pm-2:21 pm

3 stops16h 35m

Hilton Head Island

Sun 5/31

3:05 pm-11:00 pm

2 stops10h 55m

$4,428

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Sorted by cheapest first

Compare providers for flights from Portland to Hilton Head Island

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Hilton Head Island in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Portland-Hilton Head Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Hilton Head Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Hilton Head Island flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Portland to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island 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.

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. 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 Hilton Head Island. Reviews last updated April 27, 2026.
Read through reviews of airlines operating flights from Portland to Hilton Head Island, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,667 reviews

Boarding

7.5

Entertainment

6.9

Crew

7.9

Food

6.4

Comfort

7.2

Overall

7.1

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,667 reviews
American Airlines
7.1
Good
11,667 reviews

Boarding

7.5

Entertainment

6.9

Crew

7.9

Food

6.4

Comfort

7.2

Overall

7.1

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

Related info for your journey

Find useful and relevant information for your journey from Portland to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Portland to Hilton Head Island?

    Departing from Portland to Hilton Head Island will take you 7h 43m. The distance between Portland and Hilton Head Island is about 2400 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Portland to Hilton Head Island round-trip?

    American Airlines, at $367, was found to be the cheapest airline from Portland to Hilton Head Island..

  • Can I find deals for flights from Portland to Hilton Head Island that include hotel bookings?

    Yes. In addition to deals on Portland to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Hilton Head Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Hilton Head Island.

  • Can I find deals for business class flights from Portland to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Portland to Hilton Head Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort

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Top airline flying from Portland to Hilton Head Island

Discover the top airline that operate flights from Portland to Hilton Head Island. 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 April 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$367Average$702FlexibilityNo cancel feeOn-time71%

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