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Hilton Head Island

$300+ Cheap flights from Portland, ME to Hilton Head Island (PWM - 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HHH
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 (PWM) 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 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$300
(American Airlines)

Popular in

November

Cheapest in

September

Average price

$738
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 Portland to Hilton Head Island
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Highest demand for flights based on searches. 10% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 8, 2026.

This American Airlines deal was found by Cheapflights users on 1/5. 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 2/67:00 amPWM - HHH
1 stop7h 59mAmerican Airlines
Tue 2/103:29 pmHHH - PWM
1 stop6h 38mAmerican Airlines
Deal found 1/5$300
This American Airlines deal was found by Cheapflights users on 1/7. 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.
Thu 1/227:00 amPWM - HHH
1 stop5h 20mAmerican Airlines
Mon 1/263:29 pmHHH - PWM
1 stop6h 38mAmerican Airlines
Deal found 1/7$347
This American Airlines deal was found by Cheapflights users on 1/6. 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 5/211:56 amPWM - HHH
1 stop4h 38mAmerican Airlines
Sat 5/96:50 pmHHH - PWM
2 stops15h 04mAmerican Airlines
Deal found 1/6$434
This Delta deal was found by Cheapflights users on 1/6. 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 4/136:00 amPWM - HHH
1 stop5h 18mDelta
Fri 4/173:50 pmHHH - PWM
1 stop7h 34mDelta
Deal found 1/6$447
This American Airlines deal was found by Cheapflights users on 1/8. 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.
Wed 4/1511:56 amPWM - HHH
1 stop4h 38mAmerican Airlines
Thu 4/235:04 pmHHH - PWM
1 stop5h 42mAmerican Airlines
Deal found 1/8$573

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 8, 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

PWM - HHH

PWMHHH

Portland

Fri 2/6

7:00 am-2:59 pm

1 stop7h 59m

Hilton Head Island

Tue 2/10

3:29 pm-10:07 pm

1 stop6h 38m

$300

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 1/22

7:00 am-12:20 pm

1 stop5h 20m

Hilton Head Island

Mon 1/26

3:29 pm-10:07 pm

1 stop6h 38m

$347

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Wed 1/21

7:00 am-12:20 pm

1 stop5h 20m

Hilton Head Island

Sun 1/25

3:29 pm-10:07 pm

1 stop6h 38m

$347

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 1/22

7:00 am-2:59 pm

1 stop7h 59m

Hilton Head Island

Sun 1/25

3:29 pm-10:07 pm

1 stop6h 38m

$347

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 1/13

7:00 am-2:59 pm

1 stop7h 59m

$357

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 2/5

7:00 am-12:20 pm

1 stop5h 20m

$425

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

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 Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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, Maine-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, Maine-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Hilton Head Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Hilton Head Island flights, Cheapflights users trust Expedia the most. Expedia 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, Maine-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, Maine to Hilton Head Island?

Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Hilton Head Island (average of $43). Flying from Portland, Maine to Hilton Head Island in November is currently the most expensive (average of $84). 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 8, 2026.
Read reviews from past customers who have flown American Airlines from Portland to Hilton Head Island. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,094 reviews

Comfort

7.2

Crew

8.0

Food

6.4

Entertainment

6.9

Boarding

7.5

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,094 reviews
American Airlines
7.2
Good
11,094 reviews

Comfort

7.2

Crew

8.0

Food

6.4

Entertainment

6.9

Boarding

7.5

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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, Maine to Hilton Head Island?

    For as low as $300, American Airlines can have you in Hilton Head Island from Portland, Maine in 7h 59m. Portland, Maine and Hilton Head Island are separated by a distance of 969 mi.

  • What is the cheapest airline to fly from Portland, Maine to Hilton Head Island round-trip?

    Flying on American Airlines is currently your cheapest option to Hilton Head Island, with prices starting at $258. American Airlines is currently priced 50% below the average price you’ll pay for this route.

  • 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, Maine to Hilton Head Island?

    Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Hilton Head Island (average of $43). Flying from Portland, Maine to Hilton Head Island in November is currently the most expensive (average of $84). 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 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$487FlexibilityNo cancel feeOn-time71%

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