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$126+ Cheap flights from Hilton Head Island (HHH) to Maine

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.
HHH — PWM
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Maine

Cheapest flights from Hilton Head Island to Maine
Explore the most affordable flight options available from Hilton Head Island to Maine. 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 1/19. 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.
Mon 2/212:51 pm
HHH
-
BOS
1 stop5h 28m
American Airlines
Wed 2/48:30 am
BOS
-
HHH
1 stop6h 29m
American Airlines
Deal found 1/19$297
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.
Wed 4/16:15 pm
HHH
-
BOS
1 stop4h 25m
American Airlines
Sat 4/49:57 am
BOS
-
HHH
1 stop6h 04m
American Airlines
Deal found 1/19$308
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 4/2211:03 am
HHH
-
BOS
2 stops8h 29m
American Airlines
Sat 4/2510:51 am
BOS
-
HHH
1 stop7h 29m
American Airlines
Deal found 1/18$313
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.
Wed 4/82:58 pm
HHH
-
BOS
1 stop5h 07m
American Airlines
Thu 4/98:04 am
BOS
-
HHH
1 stop7h 10m
American Airlines
Deal found 1/19$328
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:00 pm
HHH
-
BOS
1 stop8h 08m
United Airlines
Sun 5/316:00 am
BOS
-
HHH
1 stop5h 12m
United Airlines
Deal found 1/19$339
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.
Sun 2/13:29 pm
HHH
-
BOS
1 stop5h 04m
American Airlines
Thu 2/58:30 am
BOS
-
HHH
1 stop6h 29m
American Airlines
Deal found 1/19$342
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 3/3112:23 pm
HHH
-
BOS
1 stop5h 34m
American Airlines
Tue 4/75:27 am
BOS
-
HHH
1 stop7h 10m
American Airlines
Deal found 1/19$347
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/13:00 pm
HHH
-
BOS
2 stops8h 59m
United Airlines
Sun 4/58:05 am
BOS
-
HHH
1 stop7h 25m
United Airlines
Deal found 1/19$349
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.
Fri 7/175:54 pm
HHH
-
PWM
1 stop4h 46m
American Airlines
Sun 7/197:23 am
PWM
-
HHH
1 stop6h 55m
American Airlines
Deal found 1/19$487
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:00 pm
HHH
-
PWM
1 stop22h 52m
United Airlines
Tue 9/16:00 am
PWM
-
HHH
1 stop5h 12m
United Airlines
Deal found 1/19$623

Find flight deals from Hilton Head Island to Maine

Keep the following information in mind while searching for Hilton Head Island to Maine flight deals. Data was last updated January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$297
(American Airlines)

One-way from

$126
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Portland flights.
Search Deals
From Hilton Head Island to Maine
Search Deals
One-way flight from Hilton Head Island to Maine
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Maine 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 Hilton Head Island to Maine that are best for you.

Fly from

Hilton Head Island

Fly to

Maine

Route

Depart

Return

Price

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Mon 2/2

12:51 pm-6:19 pm

1 stop5h 28m

Boston Logan Intl

Wed 2/4

8:30 am-2:59 pm

1 stop6h 29m

$297

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 4/1

6:15 pm-10:40 pm

1 stop4h 25m

Boston Logan Intl

Sat 4/4

9:57 am-4:01 pm

1 stop6h 04m

$308

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 4/22

3:44 pm-10:31 pm

1 stop6h 47m

Boston Logan Intl

Sat 4/25

10:51 am-4:34 pm

1 stop5h 43m

$308

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 4/8

2:58 pm-8:05 pm

1 stop5h 07m

Boston Logan Intl

Thu 4/9

8:04 am-3:14 pm

1 stop7h 10m

$328

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Thu 5/28

3:00 pm-11:08 pm

1 stop8h 08m

Boston Logan Intl

Sun 5/31

6:00 am-11:12 am

1 stop5h 12m

$339

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sun 2/1

3:29 pm-8:33 pm

1 stop5h 04m

Boston Logan Intl

Thu 2/5

8:30 am-2:59 pm

1 stop6h 29m

$342

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sat 4/4

6:15 pm-10:40 pm

1 stop4h 25m

Boston Logan Intl

Tue 4/7

10:00 am-3:14 pm

1 stop5h 14m

$347

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Fri 7/17

5:54 pm-10:40 pm

1 stop4h 46m

Portland

Sun 7/19

7:23 am-2:18 pm

1 stop6h 55m

$487

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 2/18

3:31 pm-10:15 pm

1 stop6h 44m

$126

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 7/14

4:00 pm-10:27 pm

1 stop6h 27m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 16 results
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Best time to book a flight from Hilton Head Island to Maine

Have a flexible travel schedule? Discover the best time to fly to Maine 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 Maine

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

Currently, January is the cheapest month in which you can book a flight from Hilton Head Island to Maine (average of $52). Flying from Hilton Head Island to Maine in December is currently the most expensive (average of $182). 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 Maine. 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 from for flights from Hilton Head Island to Maine?

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

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

    For as low as $297, American Airlines can have you in Maine from Hilton Head Island in 5h 28m. The distance between Hilton Head Island and Maine is about 878 mi.

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

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

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

    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 Maine.

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

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

    Currently, January is the cheapest month in which you can book a flight from Hilton Head Island to Maine (average of $52). Flying from Hilton Head Island to Maine in December is currently the most expensive (average of $182). 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

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