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Hilton Head Island

$181+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — HHH
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheap 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 September 14, 2025.

Round-trip from

$547
(American Airlines)

One-way from

$181
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$555
From Portland to Hilton Head Island
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One-way flight from Portland to Hilton Head Island
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Highest demand for flights based on searches. 11% potential increase in price ($99 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 14, 2025.

This United Airlines deal was found by Cheapflights users on 9/14. 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 9/2910:17 pmPDX - HHH
1 stop9h 59mUnited Airlines
Fri 10/311:57 amHHH - PDX
2 stops15h 31mUnited Airlines
Deal found 9/14$552
This Delta deal was found by Cheapflights users on 9/14. 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.
Wed 10/86:00 amPDX - HHH
1 stop6h 30mDelta
Wed 10/1512:17 pmHHH - PDX
1 stop9h 49mDelta
Deal found 9/14$649
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/86:25 pmPDX - HHH
2 stops13h 51mUnited Airlines
Wed 10/1511:57 amHHH - PDX
2 stops15h 31mUnited Airlines
Deal found 9/14$801
This Delta deal was found by Cheapflights users on 9/14. 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.
Sun 9/2812:45 amPDX - HHH
2 stops11h 40mDelta
Fri 10/312:14 pmHHH - PDX
2 stops13h 25mDelta
Deal found 9/14$982
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 9/299:56 pmPDX - HHH
1 stop15h 51mAmerican Airlines
Fri 10/312:56 pmHHH - PDX
1 stop10h 41mAmerican Airlines
Deal found 9/14$1,270

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 September 14, 2025.
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

Tue 3/10

10:47 pm-10:24 am

1 stop8h 37m

Hilton Head Island

Wed 3/11

4:10 pm-8:40 pm

1 stop7h 30m

$547

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Mon 9/29

10:17 pm-11:16 am

1 stop9h 59m

Hilton Head Island

Fri 10/3

11:57 am-12:28 am

2 stops15h 31m

$552

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Wed 10/8

6:00 am-3:30 pm

1 stop6h 30m

Hilton Head Island

Wed 10/15

12:17 pm-7:06 pm

1 stop9h 49m

$649

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Mon 10/6

11:58 pm-12:15 pm

2 stops9h 17m

$181

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Mon 10/6

10:17 pm-11:16 am

1 stop9h 59m

$226

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Sun 10/5

10:17 pm-11:16 am

1 stop9h 59m

$260

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Sun 10/5

12:35 am-3:30 pm

2 stops11h 55m

$485

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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, January is the cheapest month in which you can book a flight from Portland to Hilton Head Island (average of $275). Flying from Portland to Hilton Head Island in March is currently the most expensive (average of $480). 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.

What is the cheapest time of day to fly from PDX to HHH?

Find hourly flight availability from Portland to Hilton Head Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 14, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 15% on flights from Portland to Hilton Head Island by exploring options for tickets in the morning.

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 September 14, 2025.
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
10,000 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Overall

7.2

Crew

8.0

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Overall

7.2

Crew

8.0

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 8h 37m. 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.. American Airlines is priced at 49% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Portland to Hilton Head Island one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $181. United Airlines flights start at $226 while deals on Delta start at $485 one-way.

  • 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, January is the cheapest month in which you can book a flight from Portland to Hilton Head Island (average of $275). Flying from Portland to Hilton Head Island in March is currently the most expensive (average of $480). 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
Bluffton

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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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$367Average$630FlexibilityNo cancel feeOn-time71%

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