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Hilton Head Island

$119+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(American Airlines)

One-way from

$119
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$517
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. 3% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/20. 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 3/235:00 amBOS - HHH
1 stop5h 24mAmerican Airlines
Thu 3/272:49 pmHHH - BOS
1 stop5h 57mAmerican Airlines
Deal found 2/20$237
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Sat 4/59:45 amBOS - HHH
1 stop6h 19mUnited Airlines
Tue 4/84:18 pmHHH - BOS
1 stop6h 14mUnited Airlines
Deal found 2/19$238
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/286:14 amBDL - HHH
1 stop4h 09mAmerican Airlines
Wed 4/306:06 pmHHH - BDL
1 stop4h 27mAmerican Airlines
Deal found 2/19$277
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1710:00 amBDL - HHH
1 stop6h 41mDelta
Mon 5/191:15 pmHHH - BDL
1 stop7h 00mDelta
Deal found 2/20$328
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2012:00 pmBOS - HHH
1 stop4h 41mDelta
Thu 4/245:25 pmHHH - BOS
1 stop13h 55mDelta
Deal found 2/20$505
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/227:44 pmBDL - HHH
3 stops15h 37mUnited Airlines
Sat 7/2612:03 pmHHH - BDL
2 stops22h 34mUnited Airlines
Deal found 2/20$846

Find flights from Massachusetts to Hilton Head Island within your budget

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 February 20, 2025.

Fly from

Massachusetts

Fly to

Hilton Head Island

Route

Depart

Return

Price

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 3/23

5:00 am-10:24 am

1 stop5h 24m

Hilton Head Island

Thu 3/27

2:49 pm-8:46 pm

1 stop5h 57m

$237

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 4/5

9:45 am-4:04 pm

1 stop6h 19m

Hilton Head Island

Tue 4/8

4:18 pm-10:32 pm

1 stop6h 14m

$238

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sat 5/17

10:00 am-4:41 pm

1 stop6h 41m

Hilton Head Island

Mon 5/19

1:15 pm-8:15 pm

1 stop7h 00m

$328

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sat 4/5

5:02 am-11:03 am

1 stop6h 01m

Hilton Head Island

Fri 4/11

2:50 pm-6:48 pm

1 stop3h 58m

$342

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 4/20

12:00 pm-4:41 pm

1 stop4h 41m

Hilton Head Island

Thu 4/24

5:25 pm-7:20 am

1 stop13h 55m

$505

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sun 5/4

6:00 am-3:29 pm

2 stops9h 29m

Hilton Head Island

Sat 5/10

3:30 pm-11:59 pm

2 stops8h 29m

$620

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 3/18

5:00 am-10:24 am

1 stop5h 24m

$119

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Fri 3/28

6:00 am-1:29 pm

3 stops31h 29m

$565

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 5/15

5:30 am-3:29 pm

3 stops33h 59m

$693

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Massachusetts to Hilton Head Island

Get recent, data-driven insights about flights from Massachusetts to Hilton Head Island including ideal travel times, pricing trends, and more.

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 $511). 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 February 20, 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 February 20, 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
8,220 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

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
8,766 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

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
8,220 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

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 $119 on American Airlines. Other airlines that offer cheap prices include Delta from $124 and United Airlines from $159 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 $511). 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 5 airlines flying from Massachusetts to Hilton Head Island

Discover the top 5 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$88Average$236FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$116Average$164FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$152Average$366FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$270Average$507FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$283Average$623FlexibilityNo cancel feeOn-time69%
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