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Hilton Head Island

$126+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HHH
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap 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 January 20, 2026.

This American Airlines deal was found by Cheapflights users on 1/17. 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 2/116:39 am
BOS
-
HHH
1 stop5h 41m
American Airlines
Sat 2/142:58 pm
HHH
-
BOS
1 stop6h 52m
American Airlines
Deal found 1/17$251
This American Airlines deal was found by Cheapflights users on 1/18. 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 2/118:30 am
BOS
-
HHH
1 stop6h 29m
American Airlines
Mon 2/164:11 pm
HHH
-
BOS
1 stop6h 11m
American Airlines
Deal found 1/18$274
This Delta deal was found by Cheapflights users on 1/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:00 am
BOS
-
HHH
1 stop5h 23m
Delta
Thu 8/204:00 pm
HHH
-
BOS
1 stop6h 27m
Delta
Deal found 1/19$277
This American Airlines deal was found by Cheapflights users on 1/18. 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 2/197:40 am
BOS
-
HHH
1 stop6h 42m
American Airlines
Sun 2/224:11 pm
HHH
-
BOS
1 stop6h 11m
American Airlines
Deal found 1/18$287
This American Airlines deal was found by Cheapflights users on 1/19. 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.
Tue 2/36:00 am
BOS
-
HHH
2 stops8h 59m
American Airlines
Sat 2/712:54 pm
HHH
-
BOS
2 stops7h 19m
American Airlines
Deal found 1/19$288
This American Airlines deal was found by Cheapflights users on 1/18. 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 2/227:15 am
BOS
-
HHH
2 stops7h 07m
American Airlines
Thu 2/264:11 pm
HHH
-
BOS
1 stop6h 11m
American Airlines
Deal found 1/18$292
This American Airlines deal was found by Cheapflights users on 1/18. 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.
Mon 8/246:00 am
BOS
-
HHH
1 stop4h 48m
American Airlines
Mon 8/316:15 pm
HHH
-
BOS
1 stop4h 20m
American Airlines
Deal found 1/18$297
This Delta deal was found by Cheapflights users on 1/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:00 am
BOS
-
HHH
1 stop5h 23m
Delta
Tue 8/1812:00 pm
HHH
-
BOS
2 stops10h 27m
Delta
Deal found 1/19$302
This American Airlines deal was found by Cheapflights users on 1/18. 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.
Mon 2/95:20 am
PWM
-
HHH
2 stops9h 39m
American Airlines
Mon 2/166:20 pm
HHH
-
PWM
1 stop4h 30m
American Airlines
Deal found 1/18$342
This American Airlines deal was found by Cheapflights users on 1/18. 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 5/211:56 am
PWM
-
HHH
1 stop6h 24m
American Airlines
Sat 5/96:50 pm
HHH
-
PWM
2 stops15h 04m
American Airlines
Deal found 1/18$434
This American Airlines deal was found by Cheapflights users on 1/19. 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 3/267:10 am
PWM
-
HHH
1 stop7h 12m
American Airlines
Wed 4/16:15 pm
HHH
-
PWM
1 stop4h 35m
American Airlines
Deal found 1/19$483
This American Airlines deal was found by Cheapflights users on 1/19. 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 3/267:10 am
PWM
-
HHH
1 stop7h 12m
American Airlines
Tue 3/315:19 pm
HHH
-
PWM
2 stops6h 36m
American Airlines
Deal found 1/19$488

Find 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 January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$251
(American Airlines)

One-way from

$126
(American Airlines)

Popular in

November

Cheapest in

September

Average price

$738
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.
Search Deals
From Maine to Hilton Head Island
Search Deals
One-way flight from Maine to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 20, 2026.
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 2/3

6:43 am-12:20 pm

1 stop5h 37m

Hilton Head Island

Sat 2/7

3:29 pm-8:33 pm

1 stop5h 04m

$277

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 2/27

9:00 am-3:41 pm

1 stop6h 41m

Hilton Head Island

Mon 3/2

2:58 pm-9:50 pm

1 stop6h 52m

$277

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 3/5

8:00 am-3:41 pm

1 stop7h 41m

Hilton Head Island

Mon 3/9

4:11 pm-10:22 pm

1 stop6h 11m

$277

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 2/6

6:00 am-2:59 pm

2 stops8h 59m

Hilton Head Island

Mon 2/9

3:29 pm-10:22 pm

1 stop6h 53m

$282

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

8:30 am-2:59 pm

1 stop6h 29m

Hilton Head Island

Sun 2/15

2:58 pm-10:24 pm

2 stops7h 26m

$282

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 2/19

8:00 am-3:41 pm

1 stop7h 41m

Hilton Head Island

Thu 2/26

2:58 pm-10:48 pm

2 stops7h 50m

$282

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/2

6:00 am-2:59 pm

2 stops8h 59m

Hilton Head Island

Thu 2/5

12:51 pm-8:11 pm

2 stops7h 20m

$288

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Mon 2/9

5:20 am-2:59 pm

2 stops9h 39m

Hilton Head Island

Mon 2/16

6:20 pm-10:50 pm

1 stop4h 30m

$342

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 6/25

6:30 am-3:18 pm

2 stops8h 48m

Hilton Head Island

Tue 6/30

12:00 pm-6:01 pm

1 stop6h 01m

$387

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 3/17

7:00 am-11:53 am

1 stop4h 53m

Hilton Head Island

Tue 3/31

5:19 pm-11:55 pm

2 stops6h 36m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Showing 1-10 of 31 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, April is the cheapest month in which you can book a flight from Maine to Hilton Head Island (average of $82). Flying from Maine to Hilton Head Island in October is currently the most expensive (average of $142). 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 37m. American Airlines provides one of the quickest options available for as low as $277. There are 878 mi between Maine and Hilton Head Island. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, April is the cheapest month in which you can book a flight from Maine to Hilton Head Island (average of $82). Flying from Maine to Hilton Head Island in October is currently the most expensive (average of $142). 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

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Alternative routes for Maine to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$279Average$432FlexibilityNo cancel feeOn-time71%

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