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Hilton Head Island

$269+ Cheap flights from Portland to Hilton Head Island (PDX - HHH)

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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — HHH
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1711:59 pm
PDX
-
HHH
2 stops11h 25m
American Airlines
Tue 4/211:08 pm
HHH
-
PDX
1 stop10h 11m
American Airlines
Deal found 1/27$437
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/2411:35 pm
PDX
-
HHH
2 stops12h 26m
American Airlines
Thu 2/262:58 pm
HHH
-
PDX
1 stop8h 46m
American Airlines
Deal found 1/26$458
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/49:44 pm
PDX
-
HHH
1 stop9h 49m
American Airlines
Sat 4/112:54 pm
HHH
-
PDX
2 stops11h 47m
American Airlines
Deal found 1/27$530
This United Airlines deal was found by Cheapflights users on 1/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:56 pm
PDX
-
HHH
1 stop9h 16m
United Airlines
Sat 10/3112:00 pm
HHH
-
PDX
1 stop12h 21m
United Airlines
Deal found 1/26$549
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/103:22 pm
PDX
-
HHH
2 stops17h 58m
American Airlines
Sat 2/142:58 pm
HHH
-
PDX
1 stop8h 46m
American Airlines
Deal found 1/26$583

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$437
(American Airlines)

One-way from

$269
(Delta)

Popular in

March

Cheapest in

November
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
One-way flight from Portland to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
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 January 28, 2026.
Use the filters below to find and compare flights from Portland to Hilton Head Island that are best for you.

Fly from

Portland

Fly to

Hilton Head Island

Route

Depart

Return

Price

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Fri 4/17

11:59 pm-2:24 pm

2 stops11h 25m

Hilton Head Island

Tue 4/21

1:08 pm-8:19 pm

1 stop10h 11m

$437

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Tue 2/24

11:35 pm-3:01 pm

2 stops12h 26m

Hilton Head Island

Thu 2/26

2:58 pm-8:44 pm

1 stop8h 46m

$458

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Sat 4/4

9:44 pm-10:33 am

1 stop9h 49m

Hilton Head Island

Sat 4/11

2:54 pm-11:41 pm

2 stops11h 47m

$530

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Tue 2/10

3:22 pm-12:20 pm

2 stops17h 58m

Hilton Head Island

Sat 2/14

2:58 pm-8:44 pm

1 stop8h 46m

$583

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Fri 4/17

7:05 pm-2:06 pm

2 stops16h 01m

Hilton Head Island

Tue 4/21

4:11 pm-12:34 pm

3 stops23h 23m

$677

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Thu 3/19

9:44 pm-10:33 am

1 stop9h 49m

Hilton Head Island

Mon 3/23

2:58 pm-12:15 am

2 stops12h 17m

$899

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Sat 3/21

9:44 pm-10:33 am

1 stop9h 49m

Hilton Head Island

Sat 3/28

11:03 am-11:06 pm

2 stops15h 03m

$1,360

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Tue 5/26

12:40 am-3:18 pm

2 stops11h 38m

$269

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Tue 5/26

10:56 pm-11:12 am

1 stop9h 16m

$304

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Mon 5/25

10:56 pm-11:12 am

1 stop9h 16m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 11 results
1
2

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 January.
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.

Cheapflights Insights

Everything you need to know about your flight from Portland to Hilton Head Island

What is the cheapest month to book a flight from Portland to Hilton Head Island?

Currently, September is the cheapest month in which you can book a flight from Portland to Hilton Head Island (average of $194). Flying from Portland to Hilton Head Island in March is currently the most expensive (average of $319). 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.

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 January 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
7.2
Good
11,201 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,201 reviews
American Airlines
7.2
Good
11,201 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 25m. The distance between Portland and Hilton Head Island is about 2400 mi.

  • 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.. American Airlines is priced at 50% lower than the current average price of a flight leaving 3 months from now.

  • 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.

  • What is the cheapest month to book a flight from Portland to Hilton Head Island?

    Currently, September is the cheapest month in which you can book a flight from Portland to Hilton Head Island (average of $194). Flying from Portland to Hilton Head Island in March is currently the most expensive (average of $319). 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.

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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$367Average$702FlexibilityNo cancel feeOn-time71%

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