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Hilton Head Island

$119+ 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HHH
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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 11/1111:10 amBOS - HHH
1 stop7h 27mAmerican Airlines
Fri 11/147:07 pmHHH - BOS
1 stop5h 09mAmerican Airlines
Deal found 10/28$232
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/1410:59 amBOS - HHH
1 stop7h 22mAmerican Airlines
Fri 12/196:13 pmHHH - BOS
1 stop4h 24mAmerican Airlines
Deal found 10/29$238
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/196:30 amBOS - HHH
1 stop5h 59mAmerican Airlines
Sat 11/222:51 pmHHH - BOS
2 stops8h 36mAmerican Airlines
Deal found 10/28$239
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/135:25 amBOS - HHH
1 stop6h 24mAmerican Airlines
Mon 11/177:07 pmHHH - BOS
1 stop5h 09mAmerican Airlines
Deal found 10/29$267
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/116:30 amBOS - HHH
1 stop5h 59mAmerican Airlines
Wed 11/123:27 pmHHH - BOS
1 stop6h 53mAmerican Airlines
Deal found 10/28$307
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/215:43 amPWM - HHH
1 stop5h 19mAmerican Airlines
Tue 11/2511:32 amHHH - PWM
1 stop5h 08mAmerican Airlines
Deal found 10/30$407
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/145:43 amPWM - HHH
1 stop5h 15mAmerican Airlines
Sun 11/162:51 pmHHH - PWM
2 stops9h 08mAmerican Airlines
Deal found 10/29$751

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 October 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$238
(American Airlines)

One-way from

$119
(American Airlines)

Popular in

January

Cheapest in

September

Average price

$654
Provider with most accurate pricing for Portland-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Portland-Hilton Head Island flights.
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From Maine to Hilton Head Island
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One-way flight from Maine to Hilton Head Island
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Highest demand for flights based on searches. 9% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 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

Tue 11/11

11:10 am-6:37 pm

1 stop7h 27m

Hilton Head Island

Fri 11/14

7:07 pm-12:16 am

1 stop5h 09m

$232

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 12/17

6:40 am-10:59 am

1 stop4h 19m

Hilton Head Island

Mon 12/22

2:46 pm-7:18 pm

1 stop4h 32m

$238

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 11/19

6:30 am-12:29 pm

1 stop5h 59m

Hilton Head Island

Sat 11/22

2:51 pm-11:27 pm

2 stops8h 36m

$239

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 12/14

7:00 am-1:47 pm

2 stops6h 47m

Hilton Head Island

Fri 12/19

11:14 am-3:24 pm

1 stop4h 10m

$243

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 11/13

5:25 am-11:49 am

1 stop6h 24m

Hilton Head Island

Mon 11/17

7:07 pm-12:16 am

1 stop5h 09m

$267

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 1/16

8:03 pm-12:20 pm

2 stops16h 17m

Hilton Head Island

Sun 1/18

12:51 pm-10:19 pm

2 stops9h 28m

$276

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 1/21

9:45 am-2:59 pm

1 stop5h 14m

Hilton Head Island

Sun 1/25

3:29 pm-10:22 pm

1 stop6h 53m

$287

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 1/23

9:45 am-2:59 pm

1 stop5h 14m

Hilton Head Island

Tue 1/27

12:51 pm-6:22 pm

1 stop5h 31m

$287

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Mon 3/23

7:50 am-2:19 pm

1 stop6h 29m

Hilton Head Island

Fri 3/27

6:25 pm-10:30 pm

1 stop4h 05m

$479

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 3/24

7:50 am-2:19 pm

1 stop6h 29m

Hilton Head Island

Wed 3/25

6:25 pm-10:30 pm

1 stop4h 05m

$482

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 19 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 $156). 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 7h 27m. American Airlines provides one of the quickest options available for as low as $232. 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 $156). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$434FlexibilityNo cancel feeOn-time71%

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