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Hilton Head Island

$419+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — HHH
Aug 27 — Sep 31
Thu 8/27
Thu 9/3
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 July 28, 2026.

This United Airlines deal was found by Cheapflights users on 7/25. 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 9/2910:33 pm
PDX
-
HHH
1 stop11h 02m
United Airlines
Sat 10/33:00 pm
HHH
-
PDX
1 stop10h 23m
United Airlines
Deal found 7/25$419
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:00 pm
PDX
-
HHH
2 stops17h 05m
American Airlines
Tue 10/2712:29 pm
HHH
-
PDX
1 stop9h 10m
American Airlines
Deal found 7/26$491
This Delta deal was found by Cheapflights users on 7/25. 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 9/2812:25 am
PDX
-
HHH
2 stops12h 02m
Delta
Sat 10/312:17 pm
HHH
-
PDX
2 stops11h 30m
Delta
Deal found 7/25$494
This American Airlines deal was found by Cheapflights users on 7/25. 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 9/2911:06 pm
PDX
-
HHH
1 stop10h 09m
American Airlines
Sat 10/312:50 pm
HHH
-
PDX
1 stop8h 02m
American Airlines
Deal found 7/25$555
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3011:18 pm
PDX
-
HHH
1 stop10h 47m
United Airlines
Tue 9/11:50 pm
HHH
-
PDX
1 stop11h 13m
United Airlines
Deal found 7/27$566
This United Airlines deal was found by Cheapflights users on 7/25. 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 8/1811:17 pm
PDX
-
HHH
1 stop10h 48m
United Airlines
Fri 8/212:58 pm
HHH
-
PDX
2 stops34h 47m
United Airlines
Deal found 7/25$577
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:00 am
PDX
-
HHH
3 stops28h 03m
United Airlines
Wed 8/262:58 pm
HHH
-
PDX
1 stop10h 54m
United Airlines
Deal found 7/27$618
This American Airlines deal was found by Cheapflights users on 7/25. 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 8/1810:59 pm
PDX
-
HHH
1 stop9h 10m
American Airlines
Fri 8/211:52 pm
HHH
-
PDX
1 stop13h 07m
American Airlines
Deal found 7/25$641

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 July 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$419
(United Airlines)
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
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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 July 28, 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
Quickest round-trip

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Tue 9/29

10:33 pm-12:35 pm

1 stop11h 02m

Hilton Head Island

Sat 10/3

3:00 pm-10:23 pm

1 stop10h 23m

$419

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Tue 10/20

3:00 pm-11:05 am

2 stops17h 05m

Hilton Head Island

Tue 10/27

12:29 pm-6:39 pm

1 stop9h 10m

$491

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Mon 9/28

12:25 am-3:27 pm

2 stops12h 02m

Hilton Head Island

Sat 10/3

12:17 pm-8:47 pm

2 stops11h 30m

$494

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Sun 8/30

11:18 pm-1:05 pm

1 stop10h 47m

Hilton Head Island

Tue 9/1

1:50 pm-10:03 pm

1 stop11h 13m

$566

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Sat 8/22

3:43 pm-2:03 pm

2 stops19h 20m

Hilton Head Island

Wed 8/26

2:58 pm-10:52 pm

1 stop10h 54m

$577

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Mon 8/17

12:35 am-3:32 pm

2 stops11h 57m

Hilton Head Island

Fri 8/21

12:15 pm-7:16 pm

2 stops10h 01m

$669

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/25

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 July.
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 July 28, 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
11,839 reviews

Food

6.4

Overall

7.1

Crew

7.9

Entertainment

6.8

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Linda,Jul 2026

ROA - CLT

Very helpful and friendly people who pushed me where I needed to go
American Airlines
7.1
Good
11,839 reviews
American Airlines
7.1
Good
11,839 reviews

Food

6.4

Overall

7.1

Crew

7.9

Entertainment

6.8

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Linda,Jul 2026

ROA - CLT

Very helpful and friendly people who pushed me where I needed to go

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 11h 02m. 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 $378, 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 July 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$378Average$737FlexibilityNo cancel feeOn-time71%

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