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$126+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
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 January 26, 2026.

This American Airlines deal was found by Cheapflights users on 1/25. 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 2/83:29 pm
HHH
-
BOS
1 stop6h 53m
American Airlines
Wed 2/119:45 am
BOS
-
HHH
1 stop5h 14m
American Airlines
Deal found 1/25$277
This American Airlines deal was found by Cheapflights users on 1/25. 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 2/264:11 pm
HHH
-
BOS
1 stop6h 11m
American Airlines
Sun 3/15:47 am
BOS
-
HHH
1 stop4h 46m
American Airlines
Deal found 1/25$280
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/53:29 pm
HHH
-
BOS
1 stop7h 10m
American Airlines
Mon 2/169:00 am
BOS
-
HHH
1 stop6h 41m
American Airlines
Deal found 1/26$373
This American Airlines deal was found by Cheapflights users on 1/26. 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 6/35:54 pm
HHH
-
BOS
1 stop6h 40m
American Airlines
Sun 6/711:20 am
BOS
-
HHH
1 stop5h 49m
American Airlines
Deal found 1/26$388
This American Airlines deal was found by Cheapflights users on 1/25. 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 4/42:58 pm
HHH
-
BOS
1 stop6h 51m
American Airlines
Sat 4/119:00 am
BOS
-
HHH
1 stop6h 35m
American Airlines
Deal found 1/25$399
This Delta deal was found by Cheapflights users on 1/26. 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 6/312:00 pm
HHH
-
BOS
2 stops10h 27m
Delta
Sun 6/76:00 am
BOS
-
HHH
2 stops9h 18m
Delta
Deal found 1/26$439

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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$277
(American Airlines)

One-way from

$126
(American Airlines)

Popular in

February

Cheapest in

April

Average price

$277
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
Search Deals
One-way flight from Hilton Head Island to Massachusetts
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Highest demand for flights based on searches. 13% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 26, 2026.
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

Sun 2/8

3:29 pm-10:22 pm

1 stop6h 53m

Boston Logan Intl

Wed 2/11

9:45 am-2:59 pm

1 stop5h 14m

$277

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Thu 2/5

12:51 pm-10:56 pm

2 stops10h 05m

Boston Logan Intl

Mon 2/16

9:00 am-3:41 pm

1 stop6h 41m

$378

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 6/3

5:54 pm-12:34 am

1 stop6h 40m

Boston Logan Intl

Sun 6/7

6:00 am-11:10 am

1 stop5h 10m

$388

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sat 4/4

2:58 pm-9:49 pm

1 stop6h 51m

Boston Logan Intl

Sat 4/11

9:00 am-3:35 pm

1 stop6h 35m

$399

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 6/3

12:00 pm-10:27 pm

2 stops10h 27m

Boston Logan Intl

Sun 6/7

5:30 am-3:18 pm

2 stops9h 48m

$439

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 2/25

3:31 pm-10:15 pm

1 stop6h 44m

$126

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 4/28

4:00 pm-9:36 pm

1 stop5h 36m

$149

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 3/25

6:15 pm-10:40 pm

1 stop4h 25m

$149

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 4/22

4:00 pm-10:26 pm

1 stop6h 26m

$149

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 2/24

3:31 pm-10:15 pm

1 stop6h 44m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 15 results
1
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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 November is currently the most expensive (average of $93). 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.

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 January 26, 2026.
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
11,189 reviews

Crew

8.0

Boarding

7.5

Food

6.4

Entertainment

6.9

Overall

7.2

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,189 reviews
American Airlines
7.2
Good
11,189 reviews

Crew

8.0

Boarding

7.5

Food

6.4

Entertainment

6.9

Overall

7.2

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 53m. 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 November is currently the most expensive (average of $93). 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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Alternative routes for Hilton Head Island to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$334FlexibilityNo cancel feeOn-time71%

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