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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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — PWM
Aug 21 — Aug 281
Thu 8/21
Thu 8/28
1 adult, Economy
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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 August 16, 2025.

Round-trip from

$251
(American Airlines)

One-way from

$126
(Delta)
From Hilton Head Island to Maine
Search Deals
One-way flight from Hilton Head Island to Maine
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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 August 16, 2025.

This American Airlines deal was found by Cheapflights users on 8/15. 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 12/34:09 pmHHH - BOS
1 stop6h 17mAmerican Airlines
Sat 12/612:00 pmBOS - HHH
1 stop5h 30mAmerican Airlines
Deal found 8/15$251
This American Airlines deal was found by Cheapflights users on 8/15. 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 12/36:21 pmHHH - PWM
1 stop4h 03mAmerican Airlines
Sat 12/67:44 amPWM - HHH
1 stop6h 32mAmerican Airlines
Deal found 8/15$259
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/1912:56 pmHHH - BOS
1 stop7h 29mAmerican Airlines
Sun 9/215:50 amBOS - HHH
1 stop5h 40mAmerican Airlines
Deal found 8/16$297
This American Airlines deal was found by Cheapflights users on 8/15. 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 10/1411:16 amHHH - PWM
1 stop5h 25mAmerican Airlines
Sat 10/185:46 amPWM - HHH
1 stop5h 00mAmerican Airlines
Deal found 8/15$306
This United Airlines deal was found by Cheapflights users on 8/15. 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 8/3012:02 pmHHH - BOS
1 stop5h 49mUnited Airlines
Wed 9/36:00 amBOS - HHH
1 stop5h 25mUnited Airlines
Deal found 8/15$318
This American Airlines deal was found by Cheapflights users on 8/16. 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 11/2411:29 amHHH - BOS
1 stop6h 00mAmerican Airlines
Fri 11/286:40 amBOS - HHH
1 stop7h 38mAmerican Airlines
Deal found 8/16$354
This United Airlines deal was found by Cheapflights users on 8/15. 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 8/3012:02 pmHHH - PWM
2 stops7h 27mUnited Airlines
Wed 9/36:00 amPWM - HHH
1 stop5h 25mUnited Airlines
Deal found 8/15$356
This Delta deal was found by Cheapflights users on 8/16. 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.
Sun 8/314:02 pmHHH - BOS
1 stop4h 33mDelta
Thu 9/46:00 amBOS - HHH
1 stop5h 31mDelta
Deal found 8/16$367
This American Airlines deal was found by Cheapflights users on 8/16. 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 11/252:51 pmHHH - BOS
1 stop6h 03mAmerican Airlines
Fri 11/289:55 amBOS - HHH
1 stop7h 38mAmerican Airlines
Deal found 8/16$381
This American Airlines deal was found by Cheapflights users on 8/15. 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 8/303:41 pmHHH - PWM
2 stops19h 53mAmerican Airlines
Wed 9/37:00 amPWM - HHH
2 stops9h 47mAmerican Airlines
Deal found 8/15$550

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 August 16, 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

Wed 12/3

4:09 pm-10:26 pm

1 stop6h 17m

Boston Logan Intl

Sat 12/6

12:00 pm-5:30 pm

1 stop5h 30m

$251

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Wed 12/3

6:21 pm-10:24 pm

1 stop4h 03m

Portland

Sat 12/6

7:44 am-2:16 pm

1 stop6h 32m

$259

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 9/19

12:56 pm-8:25 pm

1 stop7h 29m

Boston Logan Intl

Sun 9/21

5:50 am-11:30 am

1 stop5h 40m

$297

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Tue 10/14

11:16 am-4:41 pm

1 stop5h 25m

Portland

Sat 10/18

5:46 am-10:46 am

1 stop5h 00m

$306

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sat 8/30

12:02 pm-5:51 pm

1 stop5h 49m

Boston Logan Intl

Wed 9/3

6:00 am-11:25 am

1 stop5h 25m

$318

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Mon 11/24

11:29 am-5:29 pm

1 stop6h 00m

Boston Logan Intl

Fri 11/28

6:40 am-2:18 pm

1 stop7h 38m

$354

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Sat 8/30

12:02 pm-7:29 pm

2 stops7h 27m

Portland

Wed 9/3

6:00 am-11:25 am

1 stop5h 25m

$356

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sun 8/31

4:02 pm-8:35 pm

1 stop4h 33m

Boston Logan Intl

Thu 9/4

6:00 am-11:31 am

1 stop5h 31m

$367

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 11/25

2:51 pm-8:54 pm

1 stop6h 03m

Boston Logan Intl

Fri 11/28

9:55 am-5:33 pm

1 stop7h 38m

$381

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 11/26

10:47 am-3:38 pm

1 stop4h 51m

Boston Logan Intl

Fri 11/28

9:55 am-5:33 pm

1 stop7h 38m

$381

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 18 results
1
2

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 $296). Flying from Hilton Head Island to Maine in July is currently the most expensive (average of $394). 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.

Reviews of airlines servicing Maine

Get insights into the airlines that provide service to Maine. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maine. Reviews last updated August 16, 2025.
Get a feel of what it's like to fly with American Airlines from Hilton Head Island to Maine by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Comfort

7.2

Food

6.5

Entertainment

6.9

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Comfort

7.2

Food

6.5

Entertainment

6.9

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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.

  • 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 $296). Flying from Hilton Head Island to Maine in July is currently the most expensive (average of $394). 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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Alternative routes for Hilton Head Island to Maine

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Hilton Head Island to Maine

Discover the top airline that operate flights from Hilton Head Island to Maine. 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 August 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$243Average$337FlexibilityNo cancel feeOn-time71%

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