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Hilton Head Island

$104+ Cheap flights from Maine to Hilton Head Island (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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HHH
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Find flight deals from Maine to Hilton Head Island

Cheapest flights from Maine to Hilton Head Island
Explore the most affordable flight options available from Maine to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2025.

This American Airlines deal was found by Cheapflights users on 11/20. 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 12/1412:01 pmBOS - HHH
1 stop6h 20mAmerican Airlines
Fri 12/192:46 pmHHH - BOS
1 stop4h 32mAmerican Airlines
Deal found 11/20$243
This American Airlines deal was found by Cheapflights users on 11/20. 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 12/67:30 amBOS - HHH
1 stop6h 17mAmerican Airlines
Wed 12/103:27 pmHHH - BOS
1 stop4h 45mAmerican Airlines
Deal found 11/20$251
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/36:40 amBOS - HHH
1 stop4h 19mAmerican Airlines
Sun 12/711:30 amHHH - BOS
1 stop4h 54mAmerican Airlines
Deal found 11/19$254
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Fri 12/55:34 amPWM - HHH
1 stop5h 25mAmerican Airlines
Tue 12/93:27 pmHHH - PWM
1 stop6h 10mAmerican Airlines
Deal found 11/20$317
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/45:46 amPWM - HHH
1 stop5h 13mAmerican Airlines
Mon 12/811:30 amHHH - PWM
1 stop4h 58mAmerican Airlines
Deal found 11/19$337
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Fri 11/217:30 amBOS - HHH
1 stop6h 49mAmerican Airlines
Fri 11/282:51 pmHHH - BOS
1 stop6h 03mAmerican Airlines
Deal found 11/20$522

Cheap flight deals from Maine to Hilton Head Island

Keep the following information in mind while searching for Maine to Hilton Head Island flight deals. Data was last updated November 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$222
(American Airlines)

One-way from

$104
(American Airlines)

Popular in

January

Cheapest in

September

Average price

$550
Provider with most accurate pricing for Portland-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Hilton Head Island flights.
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From Maine to Hilton Head Island
Search Deals
One-way flight from Maine to Hilton Head Island
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Highest demand for flights based on searches. 1% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
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 November 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Maine 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 November 20, 2025.
Use the filters below to find and compare flights from Maine to Hilton Head Island that are best for you.

Fly from

Maine

Fly to

Hilton Head Island

Route

Depart

Return

Price

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

6:39 am-12:20 pm

1 stop5h 41m

Hilton Head Island

Sun 2/15

4:15 pm-10:19 pm

1 stop6h 04m

$222

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 1/11

8:30 am-2:59 pm

1 stop6h 29m

Hilton Head Island

Tue 1/13

3:29 pm-10:22 pm

1 stop6h 53m

$232

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 1/8

6:39 am-12:20 pm

1 stop5h 41m

Hilton Head Island

Mon 1/12

3:29 pm-8:33 pm

1 stop5h 04m

$237

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 1/13

6:00 am-12:20 pm

2 stops6h 20m

Hilton Head Island

Thu 1/15

3:29 pm-10:19 pm

2 stops6h 50m

$242

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 12/14

12:01 pm-6:21 pm

1 stop6h 20m

Hilton Head Island

Fri 12/19

2:46 pm-7:18 pm

1 stop4h 32m

$243

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 12/6

7:30 am-1:47 pm

1 stop6h 17m

Hilton Head Island

Wed 12/10

3:27 pm-8:12 pm

1 stop4h 45m

$251

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 12/3

6:40 am-10:59 am

1 stop4h 19m

Hilton Head Island

Sun 12/7

11:30 am-4:24 pm

1 stop4h 54m

$254

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Fri 12/5

5:34 am-10:59 am

1 stop5h 25m

Hilton Head Island

Tue 12/9

3:27 pm-9:37 pm

1 stop6h 10m

$317

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 12/4

5:46 am-10:59 am

1 stop5h 13m

Hilton Head Island

Mon 12/8

11:30 am-4:28 pm

1 stop4h 58m

$337

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Sat 1/17

7:00 am-2:59 pm

1 stop7h 59m

Hilton Head Island

Wed 1/21

3:29 pm-10:07 pm

1 stop6h 38m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 18 results
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Best time to book a flight from Maine to Hilton Head Island

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

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

Currently, March is the cheapest month in which you can book a flight from Maine to Hilton Head Island (average of $88). Flying from Maine to Hilton Head Island in December is currently the most expensive (average of $149). 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 Maine 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 airport do you fly into for flights to Hilton Head Island from Maine?

    Most people fly into Hilton Head Island (HHH) if they book a flight to Hilton Head Island from Maine. Hilton Head is conveniently located just 3.3 mi from Hilton Head Island’s city center.

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

    A quick flight from Maine to Hilton Head Island can take about 5h 41m. American Airlines provides one of the quickest options available for as low as $222. There are 878 mi between Maine and Hilton Head Island.

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

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

  • How can I find direct flights from Maine 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 Maine to Hilton Head Island.

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

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

    Currently, March is the cheapest month in which you can book a flight from Maine to Hilton Head Island (average of $88). Flying from Maine to Hilton Head Island in December is currently the most expensive (average of $149). 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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Alternative routes for Maine to Hilton Head Island

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Top airline flying from Maine to Hilton Head Island

Discover the top airline that operate flights from Maine 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$433FlexibilityNo cancel feeOn-time71%

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