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Hilton Head Island

$364+ Cheap flights from Oregon to Hilton Head Island (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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — HHH
Mar 9 — Mar 161
Mon 3/9
Mon 3/16
1 adult, Economy
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Cheap 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 February 7, 2026.

This American Airlines deal was found by Cheapflights users on 2/4. 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 3/69:44 pm
PDX
-
HHH
1 stop9h 49m
American Airlines
Wed 3/112:58 pm
HHH
-
PDX
1 stop8h 46m
American Airlines
Deal found 2/4$414
This American Airlines deal was found by Cheapflights users on 2/2. 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 4/2111:23 pm
PDX
-
HHH
1 stop8h 09m
American Airlines
Tue 4/282:54 pm
HHH
-
PDX
1 stop8h 25m
American Airlines
Deal found 2/2$447
This United Airlines deal was found by Cheapflights users on 2/4. 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 2/4$549
This American Airlines deal was found by Cheapflights users on 2/5. 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 2/209:44 pm
PDX
-
HHH
1 stop9h 49m
American Airlines
Tue 2/243:31 pm
HHH
-
PDX
1 stop8h 13m
American Airlines
Deal found 2/5$564
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/279:44 pm
PDX
-
HHH
1 stop9h 49m
American Airlines
Tue 3/3112:23 pm
HHH
-
PDX
2 stops14h 57m
American Airlines
Deal found 2/2$604

Find 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 February 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$414
(American Airlines)

One-way from

$364
(American 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 Oregon to Hilton Head Island
Search Deals
One-way flight from Oregon to Hilton Head Island
Search Deals

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 February 7, 2026.
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

Fri 3/6

9:44 pm-10:33 am

1 stop9h 49m

Hilton Head Island

Wed 3/11

2:58 pm-8:44 pm

1 stop8h 46m

$414

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Tue 4/21

11:23 pm-10:32 am

1 stop8h 09m

Hilton Head Island

Tue 4/28

2:54 pm-8:19 pm

1 stop8h 25m

$447

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Fri 2/20

9:44 pm-10:33 am

1 stop9h 49m

Hilton Head Island

Tue 2/24

3:31 pm-8:44 pm

1 stop8h 13m

$564

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Fri 3/27

9:44 pm-10:33 am

1 stop9h 49m

Hilton Head Island

Tue 3/31

12:23 pm-12:20 am

2 stops14h 57m

$604

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Sat 3/14

5:38 pm-10:33 am

2 stops13h 55m

$364

PortlandHilton Head Island

PDX - HHH

PDXHHH

Portland

Fri 3/13

9:44 pm-10:33 am

1 stop9h 49m

$485

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

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 March is currently the most expensive (average of $330). 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.

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 9h 49m. 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 March is currently the most expensive (average of $330). 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 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 February 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$367Average$733FlexibilityNo cancel feeOn-time71%

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