How long is the flight from Portland, Maine to Hilton Head Island?

For as low as $259, American Airlines can have you in Hilton Head Island from Portland, Maine in 5h 15m. Portland, Maine and Hilton Head Island are separated by a distance of 969 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, 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 48% below the average price you’ll pay for this route.

What is the cheapest day to fly from Portland, Maine to Hilton Head Island?

Travelers seeking maximum savings on their Portland, Maine to Hilton Head Island flight should consider departing on Wednesday mornings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Hilton Head Island ranges from 2.4 - 7.8 inches per month. August is typically the wettest month, when rainfall can reach 7.8 in. November is typically the driest time to visit Hilton Head Island when rainfall is around 2.4 in.

If weather is an important factor for your trip to Hilton Head Island, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

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

One of the essential ways to save on airfare from Portland, Maine to Hilton Head Island is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 21% on airfare.

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 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, Maine-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

$149+ Cheap Flights from Portland, ME to Hilton Head Island

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1. Tell us where you want to go

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Cheap flight deals from Portland to Hilton Head Island

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$512 (American Airlines)
One-way from	$149 (American Airlines)
Popular in	January
Cheapest in	September
Average price	$654

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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One-way flight from Portland to Hilton Head Island

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Highest demand for flights based on searches. 9% potential increase in price ($50 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 October 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 October 2, 2025.

Fri 10/106:00 amPWM - HHH

1 stop4h 46mAmerican Airlines

Sun 10/1211:20 amHHH - PWM

1 stop5h 21mAmerican Airlines

Deal found 10/1

$592

Best flights from Portland to Hilton Head Island
Discover carefully curated flight deals from Portland to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 2, 2025.

Thu 11/135:43 amPWM - HHH

1 stop5h 15mAmerican Airlines

Tue 11/183:27 pmHHH - PWM

1 stop6h 08mAmerican Airlines

Deal found 10/2

$259

Fri 10/176:00 amPWM - HHH

1 stop5h 16mUnited Airlines

Tue 10/2111:57 amHHH - PWM

1 stop4h 47mUnited Airlines

Deal found 10/2

$455

Tue 3/247:50 amPWM - HHH

1 stop6h 29mAmerican Airlines

Wed 3/256:25 pmHHH - PWM

1 stop4h 05mAmerican Airlines

Deal found 9/29

$512

Sat 3/145:44 amPWM - HHH

2 stops8h 35mAmerican Airlines

Sat 3/216:25 pmHHH - PWM

1 stop4h 05mAmerican Airlines

Deal found 9/30

$522

Last-minute flights from Portland to Hilton Head Island
Discover last-minute flight deals from Portland to Hilton Head Island. Data last updated October 2, 2025 and is based on user searches.

Fri 10/106:00 amPWM - HHH

1 stop4h 46mAmerican Airlines

Sun 10/1211:20 amHHH - PWM

1 stop5h 21mAmerican Airlines

Deal found 10/1

$592

One-way flights from Portland to Hilton Head Island
Search for one-way flight options from Portland to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated October 2, 2025.

Tue 11/115:43 amPWM - HHH

1 stop5h 15mAmerican Airlines

Deal found 9/30

$149

Wed 10/86:00 amPWM - HHH

1 stop5h 16mUnited Airlines

Deal found 9/30

$224

Fri 10/311:05 pmPWM - HHH

2 stops22h 27mAmerican Airlines

Deal found 9/30

$243

Cheapflights Fare Finder

Use the filters below to find and compare flights from Portland to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 11/13

5:43 am-10:58 am

1 stop5h 15m

Hilton Head Island

Tue 11/18

3:27 pm-9:35 pm

1 stop6h 08m

$259

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Fri 10/17

6:00 am-11:16 am

1 stop5h 16m

Hilton Head Island

Tue 10/21

11:57 am-4:44 pm

1 stop4h 47m

$455

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 3/24

7:50 am-2:19 pm

1 stop6h 29m

Hilton Head Island

Wed 3/25

6:25 pm-10:30 pm

1 stop4h 05m

$512

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Sat 3/14

5:44 am-2:19 pm

2 stops8h 35m

Hilton Head Island

Sat 3/21

6:25 pm-10:30 pm

1 stop4h 05m

$522

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 11/11

5:43 am-10:58 am

1 stop5h 15m

$149

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Sat 11/1

5:46 am-10:46 am

1 stop5h 00m

$149

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Fri 10/31

6:00 am-10:46 am

1 stop4h 46m

$149

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Wed 10/8

6:00 am-11:16 am

1 stop5h 16m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/30

Compare providers for flights from Portland to Hilton Head Island

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 October.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust 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, 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 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, 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, January is the cheapest month in which you can book a flight from Portland, Maine to Hilton Head Island (average of $275). Flying from Portland, Maine to Hilton Head Island in March is currently the most expensive (average of $479). 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

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

11,033 reviews

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

11,033 reviews

American Airlines

7.2

Good

11,033 reviews

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

How long is the flight from Portland, Maine to Hilton Head Island?
For as low as $259, American Airlines can have you in Hilton Head Island from Portland, Maine in 5h 15m. Portland, Maine and Hilton Head Island are separated by a distance of 969 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, 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 48% 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, January is the cheapest month in which you can book a flight from Portland, Maine to Hilton Head Island (average of $275). Flying from Portland, Maine to Hilton Head Island in March is currently the most expensive (average of $479). 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.

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Beaufort

Bluffton

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Top airline flying from Portland to Hilton Head Island

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$258	Average$492	FlexibilityNo cancel fee	On-time71%

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$149+ Cheap flights from Portland, ME to Hilton Head Island (PWM - 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Portland to Hilton Head Island with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Portland to Hilton Head Island

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Portland to Hilton Head Island

Cheapest flights from Portland to Hilton Head IslandExplore 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 October 2, 2025.

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 October 2, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Portland to Hilton Head Island that are best for you.

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 October.

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.

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?

Reviews of airlines servicing Hilton Head Island

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.

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?

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

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

How can I find direct flights from Portland to Hilton Head Island?

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

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

Traveling to a place near Hilton Head Island?

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Portland to Hilton Head Island

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Top airline flying from Portland to Hilton Head Island

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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 October 2, 2025.