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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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap 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 January 26, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 2/96:39 am
BOS
-
HHH
1 stop5h 41m
American Airlines
Thu 2/122:58 pm
HHH
-
BOS
1 stop6h 52m
American Airlines
Deal found 1/26$277
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 2/96:00 am
BOS
-
HHH
2 stops6h 20m
American Airlines
Sun 2/156:20 pm
HHH
-
BOS
1 stop5h 03m
American Airlines
Deal found 1/26$282
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Thu 3/128:00 am
BOS
-
HHH
1 stop7h 41m
American Airlines
Mon 3/166:15 pm
HHH
-
BOS
1 stop4h 36m
American Airlines
Deal found 1/26$287
This American Airlines deal was found by Cheapflights users on 1/25. 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 8/247:41 am
BOS
-
HHH
1 stop6h 31m
American Airlines
Mon 8/316:15 pm
HHH
-
BOS
1 stop4h 20m
American Airlines
Deal found 1/25$297
This Delta deal was found by Cheapflights users on 1/26. 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.
Fri 5/296:00 am
BOS
-
HHH
1 stop5h 23m
Delta
Fri 6/54:00 pm
HHH
-
BOS
1 stop6h 27m
Delta
Deal found 1/26$308
This Delta deal was found by Cheapflights users on 1/26. 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 6/106:00 am
BOS
-
HHH
1 stop5h 23m
Delta
Thu 6/184:00 pm
HHH
-
BOS
1 stop15h 21m
Delta
Deal found 1/26$315
This American Airlines deal was found by Cheapflights users on 1/25. 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.
Fri 3/275:47 am
BOS
-
HHH
1 stop4h 46m
American Airlines
Mon 3/304:11 pm
HHH
-
BOS
1 stop6h 11m
American Airlines
Deal found 1/25$318
This American Airlines deal was found by Cheapflights users on 1/26. 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 3/258:00 am
BOS
-
HHH
2 stops9h 44m
American Airlines
Thu 3/264:11 pm
HHH
-
BOS
1 stop6h 11m
American Airlines
Deal found 1/26$333
This American Airlines deal was found by Cheapflights users on 1/24. 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.
Thu 2/266:00 am
BDL
-
HHH
1 stop4h 33m
American Airlines
Tue 3/33:31 pm
HHH
-
BDL
1 stop7h 13m
American Airlines
Deal found 1/24$378
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Tue 3/106:30 am
BDL
-
HHH
1 stop5h 23m
American Airlines
Mon 3/166:15 pm
HHH
-
BDL
1 stop6h 13m
American Airlines
Deal found 1/26$387
This American Airlines deal was found by Cheapflights users on 1/25. 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.
Fri 5/297:45 am
BDL
-
HHH
2 stops9h 24m
American Airlines
Wed 6/32:48 pm
HHH
-
BDL
2 stops8h 57m
American Airlines
Deal found 1/25$398
This American Airlines deal was found by Cheapflights users on 1/25. 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 3/36:30 am
BDL
-
HHH
1 stop5h 23m
American Airlines
Tue 3/105:19 pm
HHH
-
BDL
1 stop5h 25m
American Airlines
Deal found 1/25$402

Find 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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$256
(American Airlines)

One-way from

$126
(American Airlines)

Popular in

February

Cheapest in

December

Average price

$364
Provider with most accurate pricing for Boston Logan Intl-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Hilton Head Island flights.
Search Deals
From Massachusetts to Hilton Head Island
Search Deals
One-way flight from Massachusetts to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 26, 2026.
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

Mon 2/9

8:03 pm-12:20 pm

2 stops16h 17m

Hilton Head Island

Sun 2/15

6:20 pm-12:16 am

2 stops5h 56m

$262

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 2/7

7:34 pm-2:59 pm

2 stops19h 25m

Hilton Head Island

Tue 2/10

12:51 pm-6:19 pm

1 stop5h 28m

$266

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 4/20

8:04 am-3:14 pm

1 stop7h 10m

Hilton Head Island

Thu 4/23

3:44 pm-10:31 pm

1 stop6h 47m

$277

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

8:00 am-2:59 pm

2 stops6h 59m

Hilton Head Island

Thu 2/12

2:58 pm-10:48 pm

2 stops7h 50m

$288

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

6:00 am-2:59 pm

2 stops8h 59m

Hilton Head Island

Fri 2/13

2:58 pm-10:48 pm

2 stops7h 50m

$288

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 3/24

6:00 am-3:01 pm

2 stops9h 01m

Hilton Head Island

Thu 3/26

4:11 pm-10:22 pm

1 stop6h 11m

$302

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 4/9

8:04 am-3:14 pm

1 stop7h 10m

Hilton Head Island

Tue 4/21

3:44 pm-10:31 pm

1 stop6h 47m

$308

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Thu 2/26

6:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Tue 3/3

3:31 pm-10:44 pm

1 stop7h 13m

$378

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Thu 2/26

7:44 am-2:22 pm

1 stop6h 38m

Hilton Head Island

Sat 2/28

6:20 pm-11:17 pm

1 stop4h 57m

$378

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Fri 5/29

8:00 am-3:18 pm

1 stop7h 18m

Hilton Head Island

Wed 6/3

12:00 pm-6:07 pm

1 stop6h 07m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 33 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, August is the cheapest month in which you can book a flight from Massachusetts to Hilton Head Island (average of $43). Flying from Massachusetts to Hilton Head Island in November is currently the most expensive (average of $84). 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 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 $387, American Airlines can have you in Hilton Head Island from Massachusetts in 7h 18m. 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, August is the cheapest month in which you can book a flight from Massachusetts to Hilton Head Island (average of $43). Flying from Massachusetts to Hilton Head Island in November is currently the most expensive (average of $84). 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

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Alternative routes for Massachusetts to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$167Average$277FlexibilityNo cancel feeOn-time62%
DeltaCheapest$167Average$352FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$183Average$405FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$388FlexibilityNo cancel feeOn-time71%

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