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$119+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — PWM
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Find 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 October 14, 2025.

This American Airlines deal was found by Cheapflights users on 10/14. 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 12/411:30 amHHH - BOS
1 stop4h 54mAmerican Airlines
Sun 12/79:00 amBOS - HHH
1 stop4h 47mAmerican Airlines
Deal found 10/14$217
This American Airlines deal was found by Cheapflights users on 10/14. 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 12/911:30 amHHH - PWM
1 stop4h 58mAmerican Airlines
Sat 12/135:34 amPWM - HHH
1 stop6h 33mAmerican Airlines
Deal found 10/14$259
This American Airlines deal was found by Cheapflights users on 10/13. 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 10/2412:45 pmHHH - BOS
1 stop5h 25mAmerican Airlines
Tue 10/2812:03 pmBOS - HHH
1 stop4h 48mAmerican Airlines
Deal found 10/13$263
This American Airlines deal was found by Cheapflights users on 10/14. 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 10/303:32 pmHHH - BOS
1 stop6h 11mAmerican Airlines
Tue 11/46:00 amBOS - HHH
1 stop4h 58mAmerican Airlines
Deal found 10/14$278
This American Airlines deal was found by Cheapflights users on 10/14. 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 10/2912:45 pmHHH - BOS
1 stop5h 25mAmerican Airlines
Sun 11/25:00 amBOS - HHH
1 stop4h 53mAmerican Airlines
Deal found 10/14$307
This United Airlines deal was found by Cheapflights users on 10/14. 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 10/1611:57 amHHH - BOS
1 stop4h 25mUnited Airlines
Sun 10/196:00 amBOS - HHH
1 stop5h 20mUnited Airlines
Deal found 10/14$339

Cheap 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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(American Airlines)

One-way from

$119
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$263
Provider with most accurate pricing for Hilton Head Island-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Hilton Head Island-Boston Logan Intl flights.
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From Hilton Head Island to Maine
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One-way flight from Hilton Head Island to Maine
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Highest demand for flights based on searches. 9% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 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 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 October 14, 2025.
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

Fri 12/5

11:30 am-5:24 pm

1 stop5h 54m

Boston Logan Intl

Mon 12/8

6:30 am-12:22 pm

1 stop5h 52m

$217

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Tue 12/9

11:30 am-4:28 pm

1 stop4h 58m

Portland

Sat 12/13

5:34 am-12:07 pm

1 stop6h 33m

$259

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 10/24

12:45 pm-6:10 pm

1 stop5h 25m

Boston Logan Intl

Tue 10/28

12:03 pm-4:51 pm

1 stop4h 48m

$263

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 3/27

4:19 pm-10:03 pm

1 stop5h 44m

Boston Logan Intl

Tue 3/31

10:00 am-3:59 pm

1 stop5h 59m

$414

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Sat 4/4

4:10 pm-10:30 pm

1 stop6h 20m

Portland

Wed 4/8

8:02 am-12:17 pm

1 stop4h 15m

$516

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 11/12

3:27 pm-8:12 pm

1 stop4h 45m

$119

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Thu 12/11

11:30 am-5:24 pm

1 stop5h 54m

$119

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 12/12

3:27 pm-8:25 pm

1 stop4h 58m

$119

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Mon 1/12

12:51 pm-6:22 pm

1 stop5h 31m

$119

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 11/11

7:07 pm-12:16 am

1 stop5h 09m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 17 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, June is the cheapest month in which you can book a flight from Hilton Head Island to Maine (average of $77). Flying from Hilton Head Island to Maine in December is currently the most expensive (average of $173). 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 $217, American Airlines can have you in Maine from Hilton Head Island in 5h 54m. 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, June is the cheapest month in which you can book a flight from Hilton Head Island to Maine (average of $77). Flying from Hilton Head Island to Maine in December is currently the most expensive (average of $173). 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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