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Hilton Head Island

$114+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$277
(American Airlines)

One-way from

$114
(Delta)

Popular in

December

Cheapest in

January

Average price

$485
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. 5% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 31, 2025.

This American Airlines deal was found by Cheapflights users on 3/30. 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 4/265:00 amBDL - HHH
1 stop6h 03mAmerican Airlines
Wed 4/306:06 pmHHH - BDL
1 stop4h 27mAmerican Airlines
Deal found 3/30$277
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/1410:01 amBOS - HHH
1 stop7h 35mAmerican Airlines
Wed 4/1610:53 amHHH - BOS
2 stops6h 27mAmerican Airlines
Deal found 3/31$292
This Delta deal was found by Cheapflights users on 3/30. 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 7/226:00 amBOS - HHH
1 stop5h 24mDelta
Wed 7/233:58 pmHHH - BOS
1 stop18h 28mDelta
Deal found 3/30$341
This United Airlines deal was found by Cheapflights users on 3/30. 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 7/216:00 amBOS - HHH
1 stop5h 16mUnited Airlines
Wed 7/2312:02 pmHHH - BOS
1 stop4h 27mUnited Airlines
Deal found 3/30$383
This United Airlines deal was found by Cheapflights users on 3/31. 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 4/96:00 amBDL - HHH
2 stops9h 37mUnited Airlines
Sat 4/123:36 pmHHH - BDL
2 stops8h 25mUnited Airlines
Deal found 3/31$435
This Delta deal was found by Cheapflights users on 3/31. 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 6/135:35 amBDL - HHH
2 stops9h 43mDelta
Sun 6/1512:00 pmHHH - BDL
2 stops11h 56mDelta
Deal found 3/31$1,169

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 March 31, 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

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sat 4/26

5:00 am-11:03 am

1 stop6h 03m

Hilton Head Island

Wed 4/30

6:06 pm-10:33 pm

1 stop4h 27m

$277

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 4/14

10:01 am-5:36 pm

1 stop7h 35m

Hilton Head Island

Wed 4/16

10:53 am-5:20 pm

2 stops6h 27m

$292

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 7/22

6:00 am-11:24 am

1 stop5h 24m

Hilton Head Island

Wed 7/23

3:58 pm-10:26 am

1 stop18h 28m

$341

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 7/21

6:00 am-11:16 am

1 stop5h 16m

Hilton Head Island

Wed 7/23

12:02 pm-4:29 pm

1 stop4h 27m

$383

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Tue 4/29

6:00 am-3:37 pm

2 stops9h 37m

Hilton Head Island

Tue 5/6

4:10 pm-11:59 pm

3 stops31h 49m

$624

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Fri 6/13

5:35 am-3:18 pm

2 stops9h 43m

Hilton Head Island

Sun 6/15

12:00 pm-11:56 pm

2 stops11h 56m

$1,169

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 5/14

6:00 am-11:21 am

1 stop5h 21m

$114

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 6/30

5:45 am-10:33 am

1 stop4h 48m

$144

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 5/29

6:00 am-10:36 am

1 stop4h 36m

$149

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sat 4/5

5:00 am-11:03 am

1 stop6h 03m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 11 results
1
2

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 $483). 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 March 31, 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.

Rainfall in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Hilton Head Island ranges from 2.4 - 7.8 inches per month. August is typically the wettest month, when rainfall can reach 7.8 in. November is typically the driest time to visit Hilton Head Island when rainfall is around 2.4 in.

Temperature in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Hilton Head Island, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. 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 Hilton Head Island. Reviews last updated March 31, 2025.
To help decide which airline to fly from Massachusetts to Hilton Head Island, see what other customers have to say about Delta, United Airlines and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,899 reviews

Overall

8.0

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Overall

8.0

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,614 reviews
Delta
8.0
Very good
7,899 reviews

Overall

8.0

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,899 reviews

Overall

8.0

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • What are the cheapest airlines to fly from Massachusetts to Hilton Head Island one-way?

    One-way options have recently been found by users for as low as $114 on Delta. Other airlines that offer cheap prices include American Airlines from $144 and United Airlines from $149 one-way.

  • 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 $483). 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 Massachusetts?

Book flights to Massachusetts 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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$88Average$256FlexibilityNo cancel feeOn-time62%
DeltaCheapest$152Average$413FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$261Average$470FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$283Average$629FlexibilityNo cancel feeOn-time69%
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