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Hilton Head Island

$452+ Cheap flights from Oregon to Hilton Head Island (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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — HHH
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Oregon to Hilton Head Island

Keep the following information in mind while searching for Oregon to Hilton Head Island flight deals. Data was last updated November 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$493
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$448
Provider with most accurate pricing for Portland-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Portland-Hilton Head Island flights.
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From Oregon to Hilton Head Island
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Highest demand for flights based on searches. 9% potential increase in price ($82 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Oregon to Hilton Head Island

Cheapest flights from Oregon to Hilton Head Island
Explore the most affordable flight options available from Oregon to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This American Airlines deal was found by Cheapflights users on 11/3. 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 11/185:42 pmPDX - HHH
2 stops15h 47mAmerican Airlines
Sat 11/222:51 pmHHH - PDX
1 stop9h 24mAmerican Airlines
Deal found 11/3$493
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/2911:56 pmPDX - HHH
2 stops11h 23mAmerican Airlines
Thu 12/42:17 pmHHH - PDX
1 stop9h 50mAmerican Airlines
Deal found 11/3$673

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon 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 November 3, 2025.
Use the filters below to find and compare flights from Oregon to Hilton Head Island that are best for you.

Fly from

Oregon

Fly to

Hilton Head Island

Route

Depart

Return

Price

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Sun 1/11

11:59 pm-2:59 pm

2 stops12h 00m

Hilton Head Island

Thu 1/15

12:51 pm-8:24 pm

1 stop10h 33m

$452

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Tue 3/10

3:50 pm-10:24 am

2 stops15h 34m

Hilton Head Island

Wed 3/11

4:10 pm-8:40 pm

1 stop7h 30m

$524

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Sat 3/21

10:47 pm-10:24 am

1 stop8h 37m

Hilton Head Island

Wed 3/25

4:10 pm-8:40 pm

1 stop7h 30m

$1,000

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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

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

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

Currently, September is the cheapest month in which you can book a flight from Oregon to Hilton Head Island (average of $194). Flying from Oregon to Hilton Head Island in December is currently the most expensive (average of $317). 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 OR to HHH?

Find hourly flight availability from Oregon 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 November 3, 2025.

It’s typically best to fly out from Oregon to Hilton Head Island in the afternoon. Doing so could potentially save you 59% on the flight price compared to flying in the morning, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Oregon 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.

  • What airport do you fly into for flights to Hilton Head Island from Oregon?

    Hilton Head Island (HHH) is the airport you will fly into if you book a flight from Oregon to Hilton Head Island. It is only a 3.3 mi journey from Hilton Head (HHH) to Hilton Head Island’s city center.

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

    Airlines like American Airlines fly from Oregon to Hilton Head Island in about 12h. The time it takes to get you to your destination can typically vary by up to . The distance from Oregon to Hilton Head Island is about 2400 mi.

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

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

  • How can I find direct flights from Oregon 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 Oregon to Hilton Head Island.

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

    Yes. Cheapflights offers flight deals from Oregon 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 Oregon to Hilton Head Island?

    Currently, September is the cheapest month in which you can book a flight from Oregon to Hilton Head Island (average of $194). Flying from Oregon to Hilton Head Island in December is currently the most expensive (average of $317). 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 Oregon to Hilton Head Island

Discover the top airline that operate flights from Oregon 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$367Average$702FlexibilityNo cancel feeOn-time71%

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