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Hilton Head Island

$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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HHH
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$276
(Delta)

One-way from

$149
(American Airlines)
From Portland to Hilton Head Island
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One-way flight from Portland to Hilton Head Island
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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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. 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 10/226:01 amPWM - HHH
1 stop5h 26mDelta
Sat 10/2512:17 pmHHH - PWM
2 stops11h 48mDelta
Deal found 8/14$276
This Delta deal was found by Cheapflights users on 8/14. 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.
Tue 10/212:38 pmPWM - HHH
2 stops24h 52mDelta
Sat 10/2512:17 pmHHH - PWM
2 stops11h 48mDelta
Deal found 8/14$291
This Delta deal was found by Cheapflights users on 8/14. 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.
Thu 10/236:01 amPWM - HHH
1 stop5h 26mDelta
Sat 10/2512:17 pmHHH - PWM
2 stops11h 48mDelta
Deal found 8/14$305
This Delta deal was found by Cheapflights users on 8/14. 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.
Mon 10/206:01 amPWM - HHH
1 stop5h 36mDelta
Sat 10/2512:17 pmHHH - PWM
2 stops11h 48mDelta
Deal found 8/14$364
This American Airlines deal was found by Cheapflights users on 8/13. 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 10/236:00 amPWM - HHH
1 stop4h 46mAmerican Airlines
Tue 11/1111:29 amHHH - PWM
1 stop5h 10mAmerican Airlines
Deal found 8/13$403
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Wed 10/226:00 amPWM - HHH
1 stop4h 46mAmerican Airlines
Sat 10/255:57 pmHHH - PWM
1 stop5h 05mAmerican Airlines
Deal found 8/14$407
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Sun 11/165:41 amPWM - HHH
1 stop5h 18mAmerican Airlines
Sat 11/2210:47 amHHH - PWM
2 stops7h 26mAmerican Airlines
Deal found 8/12$410
This Delta deal was found by Cheapflights users on 8/14. 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 10/196:01 amPWM - HHH
1 stop5h 26mDelta
Sat 10/2512:17 pmHHH - PWM
2 stops11h 48mDelta
Deal found 8/14$429

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 August 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

PWM - HHH

PWMHHH

Portland

Wed 10/22

6:01 am-11:27 am

1 stop5h 26m

Hilton Head Island

Sat 10/25

12:17 pm-12:05 am

2 stops11h 48m

$276

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 10/21

2:38 pm-3:30 pm

2 stops24h 52m

Hilton Head Island

Sat 10/25

12:17 pm-12:05 am

2 stops11h 48m

$291

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 10/23

6:01 am-11:27 am

1 stop5h 26m

Hilton Head Island

Sat 10/25

12:17 pm-12:05 am

2 stops11h 48m

$305

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Mon 10/20

6:01 am-11:37 am

1 stop5h 36m

Hilton Head Island

Sat 10/25

12:17 pm-12:05 am

2 stops11h 48m

$364

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 10/23

6:00 am-10:46 am

1 stop4h 46m

Hilton Head Island

Tue 11/11

11:29 am-4:39 pm

1 stop5h 10m

$403

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Wed 10/22

6:00 am-10:46 am

1 stop4h 46m

Hilton Head Island

Sat 10/25

5:57 pm-11:02 pm

1 stop5h 05m

$407

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Sun 11/16

5:41 am-10:59 am

1 stop5h 18m

Hilton Head Island

Sat 11/22

10:47 am-6:13 pm

2 stops7h 26m

$410

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Sun 10/19

6:01 am-11:27 am

1 stop5h 26m

Hilton Head Island

Sat 10/25

12:17 pm-12:05 am

2 stops11h 48m

$429

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Wed 11/12

7:02 am-11:46 am

1 stop4h 44m

$149

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Sun 11/9

5:41 am-10:59 am

1 stop5h 18m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 15 results
1
2

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 $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.

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 August 14, 2025.
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
10,000 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Food

6.5

Overall

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Food

6.5

Overall

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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.

  • 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.

  • 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 $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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$485FlexibilityNo cancel feeOn-time71%

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