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$119+ Cheap flights from Hilton Head Island (HHH) to Massachusetts

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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Massachusetts

Keep the following information in mind while searching for Hilton Head Island to Massachusetts flight deals. Data was last updated October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(American Airlines)

One-way from

$119
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$263
Provider with most accurate pricing for Hilton Head Island-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Hilton Head Island-Boston Logan Intl flights.
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From Hilton Head Island to Massachusetts
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One-way flight from Hilton Head Island to Massachusetts
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Highest demand for flights based on searches. 9% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Hilton Head Island to Massachusetts

Cheapest flights from Hilton Head Island to Massachusetts
Explore the most affordable flight options available from Hilton Head Island to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 22, 2025.

This American Airlines deal was found by Cheapflights users on 10/21. 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.
Fri 12/53:27 pmHHH - BOS
1 stop7h 06mAmerican Airlines
Mon 12/86:00 amBOS - HHH
1 stop4h 59mAmerican Airlines
Deal found 10/21$217
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/53:27 pmHHH - BOS
1 stop4h 45mAmerican Airlines
Sun 11/95:25 amBOS - HHH
1 stop6h 24mAmerican Airlines
Deal found 10/21$232
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Fri 10/313:32 pmHHH - BOS
1 stop6h 27mAmerican Airlines
Tue 11/41:23 pmBOS - HHH
1 stop5h 14mAmerican Airlines
Deal found 10/19$293
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Sat 11/15:57 pmHHH - BOS
1 stop5h 03mAmerican Airlines
Tue 11/46:30 amBOS - HHH
1 stop5h 59mAmerican Airlines
Deal found 10/19$352
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Fri 10/313:32 pmHHH - BOS
1 stop6h 27mAmerican Airlines
Mon 11/36:30 amBOS - HHH
1 stop5h 59mAmerican Airlines
Deal found 10/19$354

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Massachusetts 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 October 22, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Massachusetts that are best for you.

Fly from

Hilton Head Island

Fly to

Massachusetts

Route

Depart

Return

Price

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 12/5

3:27 pm-10:33 pm

1 stop7h 06m

Boston Logan Intl

Mon 12/8

6:00 am-10:59 am

1 stop4h 59m

$217

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sat 12/6

2:17 pm-8:43 pm

1 stop6h 26m

Boston Logan Intl

Sat 1/24

8:30 am-2:59 pm

1 stop6h 29m

$217

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 12/12

3:27 pm-10:33 pm

1 stop7h 06m

Boston Logan Intl

Sun 12/14

7:30 am-1:47 pm

1 stop6h 17m

$217

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 11/5

3:27 pm-8:12 pm

1 stop4h 45m

Boston Logan Intl

Sun 11/9

5:25 am-11:49 am

1 stop6h 24m

$232

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 11/19

1:02 pm-10:22 pm

2 stops9h 20m

$124

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 12/19

2:46 pm-7:18 pm

1 stop4h 32m

$149

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sat 1/17

3:29 pm-10:22 pm

1 stop6h 53m

$150

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 12/17

3:27 pm-8:12 pm

1 stop4h 45m

$154

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 12/16

12:52 pm-8:12 pm

1 stop7h 20m

$154

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 11/18

3:27 pm-8:12 pm

1 stop4h 45m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 11 results
1
2

Best time to book a flight from Hilton Head Island to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Hilton Head Island 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 Hilton Head Island to Massachusetts

What is the cheapest month to book a flight from Hilton Head Island to Massachusetts?

Currently, June is the cheapest month in which you can book a flight from Hilton Head Island to Massachusetts (average of $37). Flying from Hilton Head Island to Massachusetts in September is currently the most expensive (average of $88). 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 HHH to MA?

Find hourly flight availability from Hilton Head Island to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 22, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 72% on flights from Hilton Head Island to Massachusetts by exploring options for tickets in the evening.

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated October 22, 2025.
Peruse reviews from past customers who have flown with American Airlines from Hilton Head Island to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,029 reviews

Overall

7.2

Crew

8.0

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,029 reviews
American Airlines
7.2
Good
11,029 reviews

Overall

7.2

Crew

8.0

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Massachusetts. 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 from for flights from Hilton Head Island to Massachusetts?

    Hilton Head Island (HHH) is the airport you will fly out of if you book a flight from Hilton Head Island to Massachusetts. It is only a 3.3 mi journey to Hilton Head (HHH) from Hilton Head Island’s city center.

  • How long is the flight from Hilton Head Island to Massachusetts?

    There are many flights that can get you from Hilton Head Island to Massachusetts in 7h 06m. Fly via American Airlines to get the fastest option. Hilton Head Island and Massachusetts are separated by a distance of 878 mi.

  • Can I find deals for flights from Hilton Head Island to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Hilton Head Island to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hilton Head Island to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Massachusetts.

  • Can I find deals for business class flights from Hilton Head Island to Massachusetts?

    Yes. Cheapflights offers flight deals from Hilton Head Island to Massachusetts 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 Hilton Head Island to Massachusetts?

    Currently, June is the cheapest month in which you can book a flight from Hilton Head Island to Massachusetts (average of $37). Flying from Hilton Head Island to Massachusetts in September is currently the most expensive (average of $88). 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

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Top airline flying from Hilton Head Island to Massachusetts

Discover the top airline that operate flights from Hilton Head Island to Massachusetts. 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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$250Average$368FlexibilityNo cancel feeOn-time71%

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