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$185+ Cheap flights from Hilton Head Island to Portland, ME (HHH - PWM)

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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — PWM
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap 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 January 28, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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 1/2812:51 pm
HHH
-
PWM
2 stops10h 52m
American Airlines
Wed 2/47:00 am
PWM
-
HHH
1 stop5h 20m
American Airlines
Deal found 1/27$394
This American Airlines deal was found by Cheapflights users on 1/25. 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 1/283:29 pm
HHH
-
PWM
1 stop6h 38m
American Airlines
Sun 2/17:00 am
PWM
-
HHH
1 stop5h 20m
American Airlines
Deal found 1/25$418
This American Airlines deal was found by Cheapflights users on 1/27. 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 1/293:29 pm
HHH
-
PWM
1 stop6h 38m
American Airlines
Wed 2/47:00 am
PWM
-
HHH
1 stop5h 20m
American Airlines
Deal found 1/27$456
This American Airlines deal was found by Cheapflights users on 1/27. 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 1/283:29 pm
HHH
-
PWM
1 stop6h 38m
American Airlines
Tue 2/37:00 am
PWM
-
HHH
1 stop5h 20m
American Airlines
Deal found 1/27$469
This American Airlines deal was found by Cheapflights users on 1/27. 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 1/283:29 pm
HHH
-
PWM
2 stops8h 14m
American Airlines
Sat 1/317:00 am
PWM
-
HHH
1 stop7h 59m
American Airlines
Deal found 1/27$474
This American Airlines deal was found by Cheapflights users on 1/27. 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 1/283:29 pm
HHH
-
PWM
1 stop6h 38m
American Airlines
Thu 2/57:00 am
PWM
-
HHH
1 stop7h 59m
American Airlines
Deal found 1/27$498
This American Airlines deal was found by Cheapflights users on 1/27. 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 1/313:29 pm
HHH
-
PWM
1 stop6h 38m
American Airlines
Wed 2/47:00 am
PWM
-
HHH
1 stop5h 20m
American Airlines
Deal found 1/27$502
This American Airlines deal was found by Cheapflights users on 1/27. 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 1/283:29 pm
HHH
-
PWM
1 stop6h 38m
American Airlines
Fri 2/65:20 am
PWM
-
HHH
2 stops9h 39m
American Airlines
Deal found 1/27$503

Find 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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars
Provider with most accurate pricing for Hilton Head Island-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Portland flights.
Search Deals

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 January 28, 2026.
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

Wed 3/4

3:31 pm-10:30 pm

1 stop6h 59m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

  • Most accurate provider: When it comes to deals on Hilton Head Island-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Hilton Head Island-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Hilton Head Island-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Hilton Head Island-Portland, Maine 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 Hilton Head Island-Portland, Maine 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 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, June is the cheapest month in which you can book a flight from Hilton Head Island to Portland, Maine (average of $37). Flying from Hilton Head Island to Portland, Maine in September is currently the most expensive (average of $88). 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 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.

  • 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, June is the cheapest month in which you can book a flight from Hilton Head Island to Portland, Maine (average of $37). Flying from Hilton Head Island to Portland, Maine in September is currently the most expensive (average of $88). 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
North Conway
Brunswick
Auburn
Conway

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