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$114+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — PWM
Dec 29 — Jan 51
Mon 12/29
Mon 1/5
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 November 29, 2025.

This American Airlines deal was found by Cheapflights users on 11/28. 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.
Fri 12/127:08 pmHHH - BOS
1 stop5h 07mAmerican Airlines
Thu 12/187:57 amBOS - HHH
1 stop6h 19mAmerican Airlines
Deal found 11/28$257
This American Airlines deal was found by Cheapflights users on 11/28. 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 12/911:30 amHHH - PWM
1 stop4h 58mAmerican Airlines
Sat 12/137:11 amPWM - HHH
1 stop6h 36mAmerican Airlines
Deal found 11/28$353
This American Airlines deal was found by Cheapflights users on 11/27. 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 12/57:08 pmHHH - BOS
1 stop5h 07mAmerican Airlines
Sun 12/77:30 amBOS - HHH
1 stop6h 17mAmerican Airlines
Deal found 11/27$407
This American Airlines deal was found by Cheapflights users on 11/28. 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.
Sat 11/296:40 pmHHH - BOS
1 stop5h 56mAmerican Airlines
Sat 12/67:30 amBOS - HHH
1 stop6h 17mAmerican Airlines
Deal found 11/28$522
This American Airlines deal was found by Cheapflights users on 11/27. 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 11/296:40 pmHHH - BOS
1 stop5h 56mAmerican Airlines
Mon 12/16:00 amBOS - HHH
1 stop5h 01mAmerican Airlines
Deal found 11/27$567

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 November 29, 2025.

Round-trip from

$222
(American Airlines)

One-way from

$114
(American Airlines)
From Hilton Head Island to Maine
Search Deals
One-way flight from Hilton Head Island to Maine
Search Deals

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 November 29, 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

Sun 1/11

3:29 pm-8:33 pm

1 stop5h 04m

Boston Logan Intl

Sun 1/18

9:45 am-2:59 pm

1 stop5h 14m

$222

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 12/12

3:27 pm-10:33 pm

1 stop7h 06m

Boston Logan Intl

Tue 12/16

8:30 am-2:57 pm

1 stop6h 27m

$257

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 12/12

7:08 pm-12:15 am

1 stop5h 07m

Boston Logan Intl

Thu 12/18

7:57 am-2:16 pm

1 stop6h 19m

$257

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sat 1/24

3:29 pm-8:33 pm

1 stop5h 04m

Boston Logan Intl

Wed 1/28

6:43 am-12:20 pm

1 stop5h 37m

$302

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Tue 1/27

3:29 pm-10:07 pm

1 stop6h 38m

Portland

Sat 1/31

7:00 am-12:20 pm

1 stop5h 20m

$353

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Tue 12/9

3:27 pm-9:37 pm

1 stop6h 10m

Portland

Sat 12/13

5:34 am-12:07 pm

1 stop6h 33m

$353

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 1/27

12:51 pm-8:11 pm

2 stops7h 20m

$119

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Mon 1/26

12:51 pm-6:19 pm

1 stop5h 28m

$119

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 12/24

2:46 pm-9:11 pm

1 stop6h 25m

$139

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Thu 12/25

11:14 am-6:32 pm

2 stops7h 18m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/28

Showing 1-10 of 14 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 $222, American Airlines can have you in Maine from Hilton Head Island in 5h 04m. 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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