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Hilton Head Island

$104+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
ene. 3 — ene. 101
sáb. 1/3
sáb. 1/10
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 diciembre 4, 2025.

This American Airlines deal was found by Cheapflights users on 12/3. 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.
jue. 12/187:57 amBOS - HHH
1 stop6h 19mAmerican Airlines
lun. 12/226:13 pmHHH - BOS
1 stop4h 24mAmerican Airlines
Deal found 12/3$277
This American Airlines deal was found by Cheapflights users on 12/4. 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.
vie. 12/199:00 amBOS - HHH
2 stops8h 43mAmerican Airlines
mar. 12/232:46 pmHHH - BOS
2 stops8h 08mAmerican Airlines
Deal found 12/4$398
This American Airlines deal was found by Cheapflights users on 12/3. 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.
jue. 12/111:37 pmBOS - HHH
1 stop4h 44mAmerican Airlines
dom. 12/1411:30 amHHH - BOS
1 stop4h 54mAmerican Airlines
Deal found 12/3$407
This American Airlines deal was found by Cheapflights users on 12/3. 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.
lun. 12/225:53 amBOS - HHH
1 stop4h 51mAmerican Airlines
mié. 12/242:46 pmHHH - BOS
1 stop6h 25mAmerican Airlines
Deal found 12/3$408
This American Airlines deal was found by Cheapflights users on 12/2. 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.
mié. 12/175:00 amBDL - HHH
1 stop5h 59mAmerican Airlines
dom. 12/2111:14 amHHH - BDL
1 stop5h 23mAmerican Airlines
Deal found 12/2$422
This American Airlines deal was found by Cheapflights users on 12/4. 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.
lun. 12/86:30 amBOS - HHH
1 stop5h 52mAmerican Airlines
vie. 12/1211:30 amHHH - BOS
1 stop4h 54mAmerican Airlines
Deal found 12/4$457
This American Airlines deal was found by Cheapflights users on 12/2. 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.
jue. 12/187:50 amBDL - HHH
1 stop6h 26mAmerican Airlines
dom. 12/216:13 pmHHH - BDL
1 stop4h 45mAmerican Airlines
Deal found 12/2$467
This American Airlines deal was found by Cheapflights users on 12/3. 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.
mié. 12/245:10 amBOS - HHH
1 stop5h 34mAmerican Airlines
jue. 1/16:13 pmHHH - BOS
1 stop4h 24mAmerican Airlines
Deal found 12/3$508
This American Airlines deal was found by Cheapflights users on 12/2. 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.
mié. 12/107:20 amBDL - HHH
1 stop5h 02mAmerican Airlines
sáb. 12/136:48 pmHHH - BDL
1 stop5h 38mAmerican Airlines
Deal found 12/2$587
This American Airlines deal was found by Cheapflights users on 12/2. 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.
jue. 12/46:08 amBDL - HHH
1 stop5h 43mAmerican Airlines
dom. 12/76:52 pmHHH - BDL
1 stop5h 34mAmerican Airlines
Deal found 12/2$687

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 diciembre 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$251
(American Airlines)

One-way from

$104
(American Airlines)

Popular in

February

Cheapest in

December

Average price

$248
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 ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 diciembre 4, 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

lun. 2/9

6:39 am-12:20 pm

1 stop5h 41m

Hilton Head Island

dom. 2/15

4:08 pm-10:19 pm

1 stop6h 11m

$252

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

sáb. 1/10

7:15 am-2:59 pm

2 stops7h 44m

Hilton Head Island

mar. 1/13

3:29 pm-11:43 pm

2 stops8h 14m

$261

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

mié. 12/17

6:40 am-10:59 am

1 stop4h 19m

Hilton Head Island

dom. 12/21

11:14 am-3:24 pm

1 stop4h 10m

$264

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

sáb. 1/10

8:30 am-2:59 pm

1 stop6h 29m

Hilton Head Island

dom. 1/11

3:29 pm-10:22 pm

1 stop6h 53m

$264

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

mar. 1/13

7:35 pm-12:20 pm

2 stops16h 45m

Hilton Head Island

dom. 1/18

3:29 pm-10:22 pm

1 stop6h 53m

$270

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

sáb. 1/10

5:14 am-2:59 pm

2 stops9h 45m

Hilton Head Island

mar. 1/13

12:51 pm-11:44 pm

2 stops10h 53m

$287

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

mié. 1/28

7:01 am-12:20 pm

1 stop5h 19m

Hilton Head Island

sáb. 1/31

12:54 pm-7:59 pm

1 stop7h 05m

$298

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

dom. 1/11

7:01 am-12:20 pm

1 stop5h 19m

Hilton Head Island

vie. 1/16

3:29 pm-11:44 pm

2 stops8h 15m

$302

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

mar. 3/10

8:48 am-3:41 pm

1 stop6h 53m

Hilton Head Island

lun. 3/16

6:20 pm-11:13 pm

1 stop4h 53m

$372

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

lun. 2/16

7:50 am-2:27 pm

1 stop6h 37m

Hilton Head Island

vie. 2/20

11:02 am-4:47 pm

1 stop5h 45m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 30 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 $85). 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 diciembre 4, 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 $252, American Airlines can have you in Hilton Head Island from Massachusetts in 5h 41m. 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 $85). 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 diciembre 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$167Average$236FlexibilityNo cancel feeOn-time62%
DeltaCheapest$167Average$362FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$253Average$387FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$582FlexibilityNo cancel feeOn-time69%

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