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

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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Sep 1 — Sep 81
Mon 9/1
Mon 9/8
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Massachusetts

Keep the following information in mind while searching for Hilton Head Island to Massachusetts flight deals. Data was last updated August 27, 2025.

Round-trip from

$259
(United Airlines)

One-way from

$126
(Delta)

Popular in

February

Cheapest in

September

Average price

$316
From Hilton Head Island to Massachusetts
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One-way flight from Hilton Head Island to Massachusetts
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Highest demand for flights based on searches. 6% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Hilton Head Island to Massachusetts

Cheapest flights from Hilton Head Island to Massachusetts
Explore the most affordable flight options available from Hilton Head Island to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 27, 2025.

This Delta deal was found by Cheapflights users on 8/26. 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 9/312:11 pmHHH - BOS
1 stop6h 20mDelta
Tue 9/98:20 amBOS - HHH
1 stop7h 02mDelta
Deal found 8/26$258
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Tue 9/912:06 pmHHH - BOS
1 stop4h 22mUnited Airlines
Sat 9/136:00 amBOS - HHH
1 stop5h 25mUnited Airlines
Deal found 8/25$259
This United Airlines deal was found by Cheapflights users on 8/25. 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 9/2412:06 pmHHH - BOS
1 stop4h 22mUnited Airlines
Mon 9/296:00 amBOS - HHH
1 stop5h 16mUnited Airlines
Deal found 8/25$319
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Tue 9/2312:06 pmHHH - BOS
2 stops6h 49mUnited Airlines
Mon 9/296:00 amBOS - HHH
1 stop5h 16mUnited Airlines
Deal found 8/25$324
This United Airlines deal was found by Cheapflights users on 8/25. 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 8/25$338
This American Airlines deal was found by Cheapflights users on 8/25. 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 9/912:56 pmHHH - BOS
2 stops9h 13mAmerican Airlines
Sat 9/137:10 amBOS - HHH
2 stops9h 37mAmerican Airlines
Deal found 8/25$353
This American Airlines deal was found by Cheapflights users on 8/25. 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 8/281:15 pmHHH - BOS
1 stop5h 39mAmerican Airlines
Mon 9/17:28 amBOS - HHH
1 stop5h 16mAmerican Airlines
Deal found 8/25$384
This Delta deal was found by Cheapflights users on 8/26. 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 9/1012:11 pmHHH - BOS
2 stops10h 49mDelta
Sun 9/146:05 amBOS - HHH
2 stops9h 20mDelta
Deal found 8/26$444
This American Airlines deal was found by Cheapflights users on 8/24. 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 8/2611:19 amHHH - ACK
1 stop5h 27mAmerican Airlines
Wed 8/271:41 pmACK - HHH
2 stops24h 31mAmerican Airlines
Deal found 8/24$948
This Delta deal was found by Cheapflights users on 8/24. 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.
Tue 8/2612:11 pmHHH - ACK
2 stops23h 15mDelta
Wed 8/273:26 pmACK - HHH
2 stops23h 56mDelta
Deal found 8/24$1,178

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Massachusetts 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 27, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Massachusetts that are best for you.

Fly from

Hilton Head Island

Fly to

Massachusetts

Route

Depart

Return

Price

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 9/10

12:06 pm-5:18 pm

1 stop5h 12m

Boston Logan Intl

Sun 9/14

6:00 am-11:25 am

1 stop5h 25m

$259

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 9/9

12:06 pm-4:28 pm

1 stop4h 22m

Boston Logan Intl

Sat 9/13

6:00 am-11:25 am

1 stop5h 25m

$259

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 9/24

12:06 pm-4:28 pm

1 stop4h 22m

Boston Logan Intl

Mon 9/29

6:00 am-11:16 am

1 stop5h 16m

$319

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 9/23

12:06 pm-6:55 pm

2 stops6h 49m

Boston Logan Intl

Mon 9/29

6:00 am-11:16 am

1 stop5h 16m

$324

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Thu 10/16

11:57 am-4:22 pm

1 stop4h 25m

Boston Logan Intl

Sun 10/19

6:00 am-11:20 am

1 stop5h 20m

$338

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 9/9

12:56 pm-10:09 pm

2 stops9h 13m

Boston Logan Intl

Sat 9/13

7:10 am-4:47 pm

2 stops9h 37m

$353

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 9/10

12:11 pm-11:00 pm

2 stops10h 49m

Boston Logan Intl

Sun 9/14

6:05 am-3:25 pm

2 stops9h 20m

$444

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 10/10

11:57 am-4:22 pm

1 stop4h 25m

Boston Logan Intl

Sun 10/12

6:00 am-11:20 am

1 stop5h 20m

$534

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 10/22

4:10 pm-10:20 pm

1 stop6h 10m

$126

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sat 10/25

3:02 pm-9:18 pm

1 stop6h 16m

$126

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/25

Showing 1-10 of 15 results
1
2

Best time to book a flight from Hilton Head Island to Massachusetts

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

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

Currently, January is the cheapest month in which you can book a flight from Hilton Head Island to Massachusetts (average of $218). Flying from Hilton Head Island to Massachusetts in July is currently the most expensive (average of $311). 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.

What is the cheapest time of day to fly from HHH to MA?

Find hourly flight availability from Hilton Head Island to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 27, 2025.

When flying from Hilton Head Island to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated August 27, 2025.
Peruse reviews from past customers who have flown with American Airlines from Hilton Head Island to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Crew

8.0

Food

6.5

Boarding

7.5

Overall

7.2

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Crew

8.0

Food

6.5

Boarding

7.5

Overall

7.2

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Massachusetts. 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 Massachusetts?

    Hilton Head Island (HHH) is the airport you will fly out of if you book a flight from Hilton Head Island to Massachusetts. It is only a 3.3 mi journey to Hilton Head (HHH) from Hilton Head Island’s city center.

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

    There are many flights that can get you from Hilton Head Island to Massachusetts in 5h 12m. Fly via United Airlines to get the fastest option. Hilton Head Island and Massachusetts are separated by a distance of 878 mi.

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

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

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

    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 Massachusetts.

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

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

    Currently, January is the cheapest month in which you can book a flight from Hilton Head Island to Massachusetts (average of $218). Flying from Hilton Head Island to Massachusetts in July is currently the most expensive (average of $311). 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 Massachusetts

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Top airline flying from Hilton Head Island to Massachusetts

Discover the top airline that operate flights from Hilton Head Island to Massachusetts. 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 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$253Average$378FlexibilityNo cancel feeOn-time71%

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