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$149+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap 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 December 4, 2025.

This American Airlines deal was found by Cheapflights users on 12/3. 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 12/242:46 pmHHH - BOS
1 stop6h 25mAmerican Airlines
Wed 1/78:03 pmBOS - HHH
2 stops16h 17mAmerican Airlines
Deal found 12/3$260
This American Airlines deal was found by Cheapflights users on 12/1. 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 12/306:13 pmHHH - BOS
1 stop4h 24mAmerican Airlines
Thu 1/112:14 pmBOS - HHH
1 stop5h 29mAmerican Airlines
Deal found 12/1$323
This American Airlines deal was found by Cheapflights users on 12/2. 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 12/127:08 pmHHH - BOS
1 stop5h 07mAmerican Airlines
Thu 12/185:53 amBOS - HHH
1 stop4h 51mAmerican Airlines
Deal found 12/2$342

Find 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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$260
(American Airlines)

One-way from

$149
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$256
Provider with most accurate pricing for Hilton Head Island-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Boston Logan Intl flights.
Search Deals
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. 11% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 4, 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

Wed 12/24

2:46 pm-9:11 pm

1 stop6h 25m

Boston Logan Intl

Wed 1/7

8:03 pm-12:20 pm

2 stops16h 17m

$260

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 1/23

3:29 pm-10:22 pm

1 stop6h 53m

Boston Logan Intl

Sun 1/25

7:35 pm-12:20 pm

2 stops16h 45m

$275

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 1/14

3:29 pm-10:22 pm

1 stop6h 53m

Boston Logan Intl

Sun 1/18

8:30 am-2:59 pm

1 stop6h 29m

$287

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 12/30

6:13 pm-10:37 pm

1 stop4h 24m

Boston Logan Intl

Thu 1/1

12:14 pm-5:43 pm

1 stop5h 29m

$323

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 12/12

7:08 pm-12:15 am

1 stop5h 07m

Boston Logan Intl

Thu 12/18

5:53 am-10:44 am

1 stop4h 51m

$342

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 3/3

4:15 pm-10:19 pm

1 stop6h 04m

$149

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sun 2/1

3:29 pm-8:33 pm

1 stop5h 04m

$149

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 2/3

12:51 pm-6:19 pm

1 stop5h 28m

$149

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Mon 3/2

4:08 pm-10:19 pm

1 stop6h 11m

$149

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Mon 2/2

3:29 pm-8:33 pm

1 stop5h 04m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

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 December 4, 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 December 4, 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
11,047 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

Food

6.5

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
American Airlines
7.2
Good
11,047 reviews
American Airlines
7.2
Good
11,047 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

Food

6.5

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.

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 6h 25m. 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.

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Alternative routes for Hilton Head Island to Massachusetts

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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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$338FlexibilityNo cancel feeOn-time71%

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