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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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(American Airlines)

One-way from

$114
(Delta)

Popular in

December

Cheapest in

January

Average price

$405

Good round-trip deal

$448 or less
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. 9% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Massachusetts to Hilton Head Island.
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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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 7/15:49 amBOS - HHH
1 stop6h 38mAmerican Airlines
Sat 7/53:33 pmHHH - BOS
Nonstop2h 33mAmerican Airlines
Deal found 4/30$229
This Delta deal was found by Cheapflights users on 4/30. 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 6/106:00 amBOS - HHH
1 stop5h 19mDelta
Wed 6/2512:00 pmHHH - BOS
2 stops10h 34mDelta
Deal found 4/30$256
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Sat 7/56:05 amBOS - HHH
1 stop5h 12mUnited Airlines
Sat 7/125:00 pmHHH - BOS
1 stop6h 12mUnited Airlines
Deal found 4/30$348
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 6/245:23 amBDL - HHH
1 stop5h 10mAmerican Airlines
Thu 6/265:50 pmHHH - BDL
1 stop4h 54mAmerican Airlines
Deal found 4/30$349
This Delta deal was found by Cheapflights users on 4/30. 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.
Mon 9/15:48 amBDL - HHH
2 stops9h 34mDelta
Mon 9/812:00 pmHHH - BDL
2 stops11h 36mDelta
Deal found 4/30$468
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/136:00 amBDL - HHH
2 stops9h 29mUnited Airlines
Tue 5/204:10 pmHHH - BDL
2 stops7h 49mUnited Airlines
Deal found 4/29$594

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 May 1, 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

Tue 7/1

5:49 am-12:27 pm

1 stop6h 38m

Hilton Head Island

Sat 7/5

3:33 pm-6:06 pm

Nonstop2h 33m

$229

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 6/10

6:00 am-11:19 am

1 stop5h 19m

Hilton Head Island

Wed 6/25

12:00 pm-10:34 pm

2 stops10h 34m

$256

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Fri 5/16

5:06 am-10:15 am

1 stop5h 09m

Hilton Head Island

Tue 5/20

12:51 pm-6:35 pm

1 stop5h 44m

$327

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 7/5

6:05 am-11:17 am

1 stop5h 12m

Hilton Head Island

Sat 7/12

5:00 pm-11:12 pm

1 stop6h 12m

$348

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Mon 9/1

5:48 am-3:22 pm

2 stops9h 34m

Hilton Head Island

Mon 9/8

12:00 pm-11:36 pm

2 stops11h 36m

$468

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Tue 5/13

6:00 am-3:29 pm

2 stops9h 29m

Hilton Head Island

Tue 5/20

4:10 pm-11:59 pm

2 stops7h 49m

$594

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 7/1

9:00 am-3:18 pm

1 stop6h 18m

$114

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 5/29

6:00 am-10:36 am

1 stop4h 36m

$149

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 7/6

5:52 am-11:27 am

1 stop5h 35m

$164

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Wed 5/28

6:10 am-10:36 am

3 stops28h 26m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 $479). 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 May 1, 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 May 1, 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
7,934 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

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
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

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
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

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
7,934 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Food

7.3

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 United Airlines from $149 and American Airlines from $164 one-way.

  • What are the cheapest flights from Massachusetts to Hilton Head Island?

    Looking for the cheapest flight from Massachusetts to Hilton Head Island? While on average our users pay $533, our data indicates the cheapest price to be $315. The most popular route (Boston Logan Intl - Hilton Head Island), is priced around $256.

  • 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 $479). 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$88Average$331FlexibilityNo cancel feeOn-time62%
DeltaCheapest$152Average$427FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$257Average$460FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$316Average$650FlexibilityNo cancel feeOn-time69%

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