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Hilton Head Island

$159+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HHH
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
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 February 11, 2026.

This American Airlines deal was found by Cheapflights users on 2/9. 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 3/316:00 am
PWM
-
HHH
2 stops10h 44m
American Airlines
Thu 4/95:04 pm
HHH
-
PWM
1 stop5h 42m
American Airlines
Deal found 2/9$315
This American Airlines deal was found by Cheapflights users on 2/8. 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 3/108:35 am
BOS
-
HHH
1 stop6h 26m
American Airlines
Tue 3/1712:23 pm
HHH
-
BOS
1 stop5h 34m
American Airlines
Deal found 2/8$317
This American Airlines deal was found by Cheapflights users on 2/8. 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 5/1210:47 am
PWM
-
HHH
1 stop4h 27m
American Airlines
Tue 5/192:54 pm
HHH
-
PWM
1 stop7h 19m
American Airlines
Deal found 2/8$336
This American Airlines deal was found by Cheapflights users on 2/10. 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 5/59:15 am
BOS
-
HHH
2 stops8h 06m
American Airlines
Sat 5/92:54 pm
HHH
-
BOS
2 stops8h 45m
American Airlines
Deal found 2/10$368
This American Airlines deal was found by Cheapflights users on 2/9. 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 5/26:00 am
PWM
-
HHH
1 stop7h 40m
American Airlines
Sat 5/95:04 pm
HHH
-
PWM
1 stop5h 42m
American Airlines
Deal found 2/9$369
This United Airlines deal was found by Cheapflights users on 2/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
BOS
-
HHH
1 stop6h 52m
United Airlines
Fri 6/53:00 pm
HHH
-
BOS
1 stop18h 39m
United Airlines
Deal found 2/8$379
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/48:00 am
BOS
-
HHH
1 stop7h 41m
American Airlines
Sat 3/74:31 pm
HHH
-
BOS
1 stop5h 51m
American Airlines
Deal found 2/10$398
This American Airlines deal was found by Cheapflights users on 2/10. 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 3/2410:00 am
BOS
-
HHH
1 stop6h 44m
American Airlines
Mon 3/304:11 pm
HHH
-
BOS
1 stop6h 11m
American Airlines
Deal found 2/10$400
This Delta deal was found by Cheapflights users on 2/11. 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.
Wed 5/69:30 am
BOS
-
HHH
1 stop5h 50m
Delta
Sun 5/104:05 pm
HHH
-
BOS
1 stop6h 20m
Delta
Deal found 2/11$403
This American Airlines deal was found by Cheapflights users on 2/10. 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 5/1610:51 am
BOS
-
HHH
1 stop5h 43m
American Airlines
Sat 5/233:39 pm
HHH
-
BOS
Nonstop2h 38m
American Airlines
Deal found 2/10$430
This American Airlines deal was found by Cheapflights users on 2/9. 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 4/1011:56 am
PWM
-
HHH
1 stop4h 38m
American Airlines
Mon 4/135:04 pm
HHH
-
PWM
1 stop5h 42m
American Airlines
Deal found 2/9$430

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 February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$315
(American Airlines)

One-way from

$159
(United Airlines)

Popular in

November

Cheapest in

September

Average price

$466
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. 20% potential increase in price ($120 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 11, 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

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 3/31

6:00 am-4:44 pm

2 stops10h 44m

Hilton Head Island

Thu 4/9

5:04 pm-10:46 pm

1 stop5h 42m

$315

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 3/10

8:35 am-3:01 pm

1 stop6h 26m

Hilton Head Island

Tue 3/17

12:23 pm-5:57 pm

1 stop5h 34m

$317

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 5/12

7:00 am-3:22 pm

2 stops8h 22m

Hilton Head Island

Tue 5/19

4:05 pm-9:33 pm

1 stop5h 28m

$322

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 5/12

10:47 am-3:14 pm

1 stop4h 27m

Hilton Head Island

Tue 5/19

2:54 pm-10:13 pm

1 stop7h 19m

$336

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Sat 5/2

6:00 am-1:40 pm

1 stop7h 40m

Hilton Head Island

Sat 5/9

5:04 pm-10:46 pm

1 stop5h 42m

$369

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 5/29

8:00 am-12:52 pm

1 stop4h 52m

Hilton Head Island

Fri 6/5

3:00 pm-12:59 am

1 stop9h 59m

$397

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 4/7

7:15 am-12:37 pm

1 stop5h 22m

Hilton Head Island

Sat 4/11

4:10 pm-11:39 pm

1 stop7h 29m

$398

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 3/4

12:15 pm-4:44 pm

1 stop4h 29m

Hilton Head Island

Sat 3/7

6:20 pm-10:40 pm

1 stop4h 20m

$398

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 4/3

10:56 am-5:44 pm

1 stop6h 48m

Hilton Head Island

Tue 4/7

2:54 pm-8:36 pm

1 stop5h 42m

$398

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 4/8

8:04 am-3:14 pm

1 stop7h 10m

Hilton Head Island

Sat 4/11

4:10 pm-11:39 pm

1 stop7h 29m

$398

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

Showing 1-10 of 22 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 $66). 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 8h 22m. American Airlines provides one of the quickest options available for as low as $322. 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 $66). 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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$382FlexibilityNo cancel feeOn-time71%

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