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$259+ Cheap flights from Hilton Head Island to Portland, ME (HHH - PWM)

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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — PWM
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to Portland (PWM). 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 agosto 14, 2025.

Round-trip from

$259
(Delta)
From Hilton Head Island to Portland
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Find flight deals from Hilton Head Island to Portland

Cheapest flights from Hilton Head Island to Portland
Explore the most affordable flight options available from Hilton Head Island to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 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.
lun. 9/84:02 pmHHH - PWM
1 stop7h 23mDelta
mar. 9/166:00 amPWM - HHH
1 stop5h 30mDelta
Deal found 8/14$259
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.
lun. 9/85:20 pmHHH - PWM
1 stop5h 09mAmerican Airlines
mar. 9/168:02 amPWM - HHH
2 stops8h 45mAmerican Airlines
Deal found 8/14$264
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.
mar. 10/1411:16 amHHH - PWM
1 stop5h 25mAmerican Airlines
sáb. 10/185:46 amPWM - HHH
1 stop5h 00mAmerican Airlines
Deal found 8/13$271
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.
vie. 10/175:57 pmHHH - PWM
1 stop5h 05mAmerican Airlines
lun. 10/206:00 amPWM - HHH
1 stop4h 46mAmerican Airlines
Deal found 8/13$384

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Portland 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 agosto 14, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Portland that are best for you.

Fly from

Hilton Head Island

Fly to

Portland

Route

Depart

Return

Price

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

lun. 9/8

4:02 pm-11:25 pm

1 stop7h 23m

Portland

mar. 9/16

6:00 am-11:30 am

1 stop5h 30m

$259

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

lun. 9/8

5:20 pm-10:29 pm

1 stop5h 09m

Portland

mar. 9/16

8:02 am-4:47 pm

2 stops8h 45m

$264

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

mar. 10/14

11:16 am-4:41 pm

1 stop5h 25m

Portland

sáb. 10/18

5:46 am-10:46 am

1 stop5h 00m

$271

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

vie. 10/17

5:57 pm-11:02 pm

1 stop5h 05m

Portland

lun. 10/20

6:00 am-10:46 am

1 stop4h 46m

$384

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

lun. 8/25

12:02 pm-6:26 pm

1 stop6h 24m

$342

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

lun. 8/25

12:11 pm-11:25 pm

2 stops11h 14m

$524

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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

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

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

Currently, January is the cheapest month in which you can book a flight from Hilton Head Island to Portland, Maine (average of $296). Flying from Hilton Head Island to Portland, Maine in July is currently the most expensive (average of $394). 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 Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated agosto 14, 2025.
Peruse reviews from past customers who have flown with American Airlines from Hilton Head Island to Portland to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Comfort

7.2

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.5

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

Crew

8.0

Comfort

7.2

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.5

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 Hilton Head Island to Portland. 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 Hilton Head Island to Portland, Maine round-trip?

    American Airlines, at $243, was found to be the cheapest airline from Hilton Head Island to Portland, Maine..

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Portland.

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

    Yes. Cheapflights offers flight deals from Hilton Head Island to Portland 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 Hilton Head Island to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Hilton Head Island to Portland, Maine (average of $296). Flying from Hilton Head Island to Portland, Maine in July is currently the most expensive (average of $394). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Brunswick
North Conway
Auburn
Conway
Lewiston

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Top airline flying from Hilton Head Island to Portland

Discover the top airline that operate flights from Hilton Head Island to Portland. 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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$243Average$337FlexibilityNo cancel feeOn-time71%

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