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$149+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — PWM
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$259
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$263
Provider with most accurate pricing for Hilton Head Island-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Hilton Head Island-Boston Logan Intl flights.
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From Hilton Head Island to Portland
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Highest demand for flights based on searches. 9% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 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 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 October 14, 2025.

This American Airlines deal was found by Cheapflights users on 10/14. 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.
Tue 12/911:30 amHHH - PWM
1 stop4h 58mAmerican Airlines
Sat 12/135:34 amPWM - HHH
1 stop6h 33mAmerican Airlines
Deal found 10/14$259

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 October 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

Tue 12/9

11:30 am-4:28 pm

1 stop4h 58m

Portland

Sat 12/13

5:34 am-12:07 pm

1 stop6h 33m

$259

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Sat 4/4

4:10 pm-10:30 pm

1 stop6h 20m

Portland

Wed 4/8

8:02 am-12:17 pm

1 stop4h 15m

$516

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Tue 11/18

11:28 am-4:41 pm

1 stop5h 13m

$149

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Mon 10/20

5:57 pm-11:02 pm

1 stop5h 05m

$239

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Sun 10/26

4:10 pm-11:09 pm

1 stop6h 59m

$529

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Sun 10/26

3:02 pm-11:51 pm

2 stops8h 49m

$586

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

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.

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

    American Airlines can get you from Hilton Head Island to Portland, Maine in just under 4h 58m. Your travel time can differ by up to . The distance between Hilton Head Island and Portland, Maine is about 969 mi.

  • 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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