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Hilton Head Island

$144+ 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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Jun 22 — Jun 291
Sun 6/22
Sun 6/29
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 June 17, 2025.

Round-trip from

$249
(American Airlines)

One-way from

$144
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$364
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 ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 17, 2025.

This American Airlines deal was found by Cheapflights users on 6/15. 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 8/148:20 amBDL - HHH
1 stop4h 24mAmerican Airlines
Thu 8/216:15 pmHHH - BDL
1 stop6h 17mAmerican Airlines
Deal found 6/15$249
This American Airlines deal was found by Cheapflights users on 6/15. 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 10/17:45 amBOS - HHH
1 stop4h 32mAmerican Airlines
Sat 10/43:26 pmHHH - BOS
1 stop6h 15mAmerican Airlines
Deal found 6/15$251
This Delta deal was found by Cheapflights users on 6/15. 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.
Wed 6/256:00 amBOS - HHH
1 stop5h 19mDelta
Mon 6/303:58 pmHHH - BOS
1 stop4h 28mDelta
Deal found 6/15$264
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Sun 8/316:00 amBOS - HHH
1 stop5h 21mUnited Airlines
Sat 9/612:06 pmHHH - BOS
1 stop4h 22mUnited Airlines
Deal found 6/17$428
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Fri 8/156:10 amBDL - HHH
2 stops31h 51mUnited Airlines
Tue 8/1912:06 pmHHH - BDL
2 stops21h 30mUnited Airlines
Deal found 6/16$756
This United deal was found by Cheapflights users on 6/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/286:05 amBOS - HHH
1 stop5h 12mMultiple Airlines
Sat 7/512:02 pmHHH - BOS
2 stops31h 04mMultiple Airlines
Deal found 6/15$1,475

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 June 17, 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

Thu 8/14

8:20 am-12:44 pm

1 stop4h 24m

Hilton Head Island

Thu 8/21

6:15 pm-12:32 am

1 stop6h 17m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 6/25

6:00 am-11:19 am

1 stop5h 19m

Hilton Head Island

Mon 6/30

3:58 pm-8:26 pm

1 stop4h 28m

$264

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 7/19

12:19 pm-3:03 pm

Nonstop2h 44m

Hilton Head Island

Sat 7/26

3:33 pm-6:06 pm

Nonstop2h 33m

$267

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 8/31

6:00 am-11:21 am

1 stop5h 21m

Hilton Head Island

Sat 9/6

12:06 pm-4:28 pm

1 stop4h 22m

$428

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Fri 8/15

6:10 am-2:01 pm

2 stops31h 51m

Hilton Head Island

Tue 8/19

12:06 pm-9:36 am

2 stops21h 30m

$756

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 6/28

6:05 am-11:17 am

1 stop5h 12m

Hilton Head Island

Sat 7/5

12:02 pm-7:06 pm

2 stops31h 04m

$1,475

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 7/7

5:55 am-12:46 pm

1 stop6h 51m

$144

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 6/25

6:00 am-11:19 am

1 stop5h 19m

$164

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 6/27

6:05 am-11:17 am

1 stop5h 12m

$190

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sun 7/27

5:55 am-11:27 am

1 stop5h 32m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 12 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 $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 June 17, 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 June 17, 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
7,965 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,965 reviews
Delta
8.0
Very good
7,965 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,809 reviews
Delta
8.0
Very good
7,965 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,965 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $144 on American Airlines. Other airlines that offer cheap prices include Delta from $164 and United Airlines from $190 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 $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 June 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$98Average$227FlexibilityNo cancel feeOn-time62%
DeltaCheapest$152Average$427FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$267Average$461FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$638FlexibilityNo cancel feeOn-time69%

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