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Hilton Head Island

$115+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(American Airlines)

One-way from

$115
(American Airlines)

Popular in

February

Cheapest in

December

Average price

$342
Provider with most accurate pricing for Boston Logan Intl-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Hilton Head Island flights.
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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 ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 22, 2025.

This American Airlines deal was found by Cheapflights users on 10/20. 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 12/49:01 amBOS - HHH
1 stop4h 46mAmerican Airlines
Mon 12/812:52 pmHHH - BOS
1 stop4h 43mAmerican Airlines
Deal found 10/20$217
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/1512:11 pmBOS - HHH
1 stop6h 06mAmerican Airlines
Mon 11/177:07 pmHHH - BOS
1 stop5h 09mAmerican Airlines
Deal found 10/21$247
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/56:00 amBOS - HHH
1 stop4h 58mAmerican Airlines
Sat 11/812:38 pmHHH - BOS
1 stop6h 22mAmerican Airlines
Deal found 10/21$278
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/275:25 amBOS - HHH
1 stop4h 59mAmerican Airlines
Thu 12/42:17 pmHHH - BOS
2 stops7h 59mAmerican Airlines
Deal found 10/21$283
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/56:00 amBOS - HHH
1 stop4h 59mAmerican Airlines
Sun 12/711:30 amHHH - BOS
1 stop4h 54mAmerican Airlines
Deal found 10/21$288
This American Airlines deal was found by Cheapflights users on 10/20. 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 10/277:32 amBOS - HHH
1 stop7h 00mAmerican Airlines
Mon 11/33:27 pmHHH - BOS
1 stop6h 53mAmerican Airlines
Deal found 10/20$297
This American Airlines deal was found by Cheapflights users on 10/20. 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 11/156:09 amBDL - HHH
1 stop5h 07mAmerican Airlines
Tue 11/187:07 pmHHH - BDL
1 stop4h 51mAmerican Airlines
Deal found 10/20$337
This American Airlines deal was found by Cheapflights users on 10/20. 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 11/45:06 amBDL - HHH
1 stop5h 52mAmerican Airlines
Sat 11/812:38 pmHHH - BDL
1 stop3h 53mAmerican Airlines
Deal found 10/20$359
This American Airlines deal was found by Cheapflights users on 10/20. 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 11/1012:45 pmBDL - HHH
1 stop5h 52mAmerican Airlines
Sat 11/156:48 pmHHH - BDL
1 stop4h 41mAmerican Airlines
Deal found 10/20$372
This American Airlines deal was found by Cheapflights users on 10/20. 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 11/97:57 amBDL - HHH
1 stop6h 22mAmerican Airlines
Sat 11/156:48 pmHHH - BDL
1 stop4h 41mAmerican Airlines
Deal found 10/20$392
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/145:06 amBDL - HHH
1 stop5h 52mAmerican Airlines
Mon 11/173:27 pmHHH - BDL
1 stop4h 30mAmerican Airlines
Deal found 10/21$407

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 October 22, 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

Fri 12/5

1:28 pm-6:33 pm

1 stop5h 05m

Hilton Head Island

Fri 12/12

3:27 pm-10:33 pm

1 stop7h 06m

$217

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 2/6

8:30 am-2:59 pm

1 stop6h 29m

Hilton Head Island

Mon 2/9

3:29 pm-10:22 pm

1 stop6h 53m

$217

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

9:45 am-2:59 pm

1 stop5h 14m

Hilton Head Island

Sun 2/15

4:19 pm-10:30 pm

1 stop6h 11m

$247

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 11/27

5:25 am-10:24 am

1 stop4h 59m

Hilton Head Island

Thu 12/4

11:30 am-5:24 pm

1 stop5h 54m

$278

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 2/21

10:00 am-3:59 pm

1 stop5h 59m

Hilton Head Island

Tue 2/24

4:02 pm-8:08 pm

1 stop4h 06m

$310

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 2/18

10:00 am-3:59 pm

1 stop5h 59m

Hilton Head Island

Tue 2/24

4:02 pm-8:08 pm

1 stop4h 06m

$310

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sat 11/15

6:09 am-11:16 am

1 stop5h 07m

Hilton Head Island

Tue 11/18

7:07 pm-11:58 pm

1 stop4h 51m

$337

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Mon 11/10

12:45 pm-6:37 pm

1 stop5h 52m

Hilton Head Island

Sat 11/15

6:48 pm-11:29 pm

1 stop4h 41m

$372

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sun 11/9

7:57 am-2:19 pm

1 stop6h 22m

Hilton Head Island

Sat 11/15

6:48 pm-11:29 pm

1 stop4h 41m

$392

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Fri 11/14

5:06 am-10:58 am

1 stop5h 52m

Hilton Head Island

Mon 11/17

3:27 pm-7:57 pm

1 stop4h 30m

$407

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 23 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 $83). 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 October 22, 2025.

A simple way to save on the total cost of your ticket is to fly from Massachusetts to Hilton Head Island in the evening. If you’re flexible enough to do this you can expect to save up to 70% on your trip compared to booking a flight at noon.

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 $217, American Airlines can have you in Hilton Head Island from Massachusetts in 5h 05m. There are 878 mi between Massachusetts and Hilton Head Island.

  • 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 $83). 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

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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$167Average$236FlexibilityNo cancel feeOn-time62%
DeltaCheapest$167Average$362FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$255Average$396FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$614FlexibilityNo cancel feeOn-time69%

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