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Hilton Head Island

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

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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Sep 1 — Sep 81
Mon 9/1
Mon 9/8
1 adult, Economy
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Cheap flight deals from Massachusetts to Hilton Head Island

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

Round-trip from

$249
(Delta)

One-way from

$126
(Delta)

Popular in

December

Cheapest in

January

Average price

$362
From Massachusetts to Hilton Head Island
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One-way flight from Massachusetts to Hilton Head Island
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Highest demand for flights based on searches. 8% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 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 Massachusetts to Hilton Head Island

Cheapest flights from Massachusetts to Hilton Head Island
Explore the most affordable flight options available from Massachusetts to Hilton Head Island. 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.
Mon 9/228:05 amBOS - HHH
1 stop7h 20mDelta
Mon 9/294:05 pmHHH - BOS
1 stop6h 15mDelta
Deal found 8/26$249
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Tue 9/235:15 amBDL - HHH
1 stop5h 19mAmerican Airlines
Tue 9/3011:04 amHHH - BDL
1 stop6h 03mAmerican Airlines
Deal found 8/27$249
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.
Sat 9/202:16 pmBOS - HHH
1 stop4h 38mAmerican Airlines
Sat 9/277:24 pmHHH - BOS
1 stop4h 11mAmerican Airlines
Deal found 8/25$251
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/105:15 amBDL - HHH
1 stop5h 19mAmerican Airlines
Tue 9/1611:04 amHHH - BDL
1 stop6h 03mAmerican Airlines
Deal found 8/26$254
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 9/238:19 amBOS - HHH
2 stops8h 28mAmerican Airlines
Wed 10/112:56 pmHHH - BOS
1 stop4h 43mAmerican Airlines
Deal found 8/24$256
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 9/1010:10 amBOS - HHH
1 stop5h 12mDelta
Mon 9/154:05 pmHHH - BOS
1 stop5h 24mDelta
Deal found 8/26$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.
Mon 9/16:00 amBOS - HHH
1 stop5h 21mUnited Airlines
Fri 9/512:06 pmHHH - BOS
1 stop4h 41mUnited Airlines
Deal found 8/25$269
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/132:16 pmBOS - HHH
1 stop4h 38mAmerican Airlines
Tue 9/1612:56 pmHHH - BOS
1 stop7h 29mAmerican Airlines
Deal found 8/26$274
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1510:35 amBOS - HHH
1 stop6h 16mAmerican Airlines
Mon 10/205:57 pmHHH - BOS
1 stop5h 03mAmerican Airlines
Deal found 8/26$281
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Sun 10/56:00 amBOS - HHH
2 stops8h 06mAmerican Airlines
Wed 10/83:32 pmHHH - BOS
2 stops6h 47mAmerican Airlines
Deal found 8/27$284
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.
Mon 9/16:12 amBDL - HHH
1 stop5h 18mAmerican Airlines
Mon 9/85:20 pmHHH - BDL
1 stop6h 09mAmerican Airlines
Deal found 8/25$284
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Thu 10/25:15 amBDL - HHH
1 stop5h 19mAmerican Airlines
Tue 10/75:21 pmHHH - BDL
1 stop4h 40mAmerican Airlines
Deal found 8/27$293

Cheapflights Fare Finder

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

Fly from

Massachusetts

Fly to

Hilton Head Island

Route

Depart

Return

Price

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 9/25

6:00 am-11:30 am

1 stop5h 30m

Hilton Head Island

Mon 9/29

4:05 pm-10:20 pm

1 stop6h 15m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 9/24

6:00 am-11:25 am

1 stop5h 25m

Hilton Head Island

Wed 10/1

11:57 am-4:22 pm

1 stop4h 25m

$249

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Tue 9/23

5:15 am-10:34 am

1 stop5h 19m

Hilton Head Island

Tue 9/30

11:04 am-5:07 pm

1 stop6h 03m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 9/23

8:05 am-3:25 pm

1 stop7h 20m

Hilton Head Island

Wed 10/1

4:05 pm-10:20 pm

1 stop6h 15m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 9/23

6:00 am-11:25 am

1 stop5h 25m

Hilton Head Island

Wed 10/1

11:57 am-4:22 pm

1 stop4h 25m

$249

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Wed 12/17

12:38 pm-6:38 pm

1 stop6h 00m

Hilton Head Island

Mon 1/5

6:13 pm-12:18 am

1 stop6h 05m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 10/3

6:00 am-11:30 am

1 stop5h 30m

Hilton Head Island

Mon 10/6

4:10 pm-9:27 pm

1 stop5h 17m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 9/22

6:00 am-11:30 am

1 stop5h 30m

Hilton Head Island

Mon 9/29

4:05 pm-10:20 pm

1 stop6h 15m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 9/20

2:16 pm-6:54 pm

1 stop4h 38m

Hilton Head Island

Sat 9/27

7:24 pm-11:35 pm

1 stop4h 11m

$251

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 9/23

7:45 am-12:17 pm

1 stop4h 32m

Hilton Head Island

Wed 10/1

12:56 pm-5:39 pm

1 stop4h 43m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/25

Showing 1-10 of 26 results
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Best time to book a flight from Massachusetts to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Massachusetts 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 Massachusetts to Hilton Head Island

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

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Hilton Head Island (average of $275). Flying from Massachusetts to Hilton Head Island in March is currently the most expensive (average of $479). 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 MA to HHH?

Find hourly flight availability from Massachusetts to Hilton Head Island. 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.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Massachusetts to Hilton Head Island as you normally would.

Related info for your journey

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

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

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

    For as low as $249, Delta can have you in Hilton Head Island from Massachusetts in 5h 19m. There are 802 mi between Massachusetts and Hilton Head Island. This flight may include one or multiple stops.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Hilton Head Island.

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

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

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Hilton Head Island (average of $275). Flying from Massachusetts to Hilton Head Island in March is currently the most expensive (average of $479). 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

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton

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Alternative routes for Massachusetts to Hilton Head Island

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Top 4 airlines flying from Massachusetts to Hilton Head Island

Discover the top 4 airlines that operate flights from Massachusetts to Hilton Head Island. 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
JetBlueCheapest$133Average$277FlexibilityNo cancel feeOn-time62%
DeltaCheapest$167Average$399FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$259Average$423FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$638FlexibilityNo cancel feeOn-time69%

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