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$144+ 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 7/24. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$231
(American Airlines)

One-way from

$144
(Delta)

Popular in

July

Cheapest in

April

Average price

$554
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. 17% potential increase in price ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/1. 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.
Sat 8/93:41 pmHHH - BOS
Nonstop2h 35mAmerican Airlines
Sat 8/1612:25 pmBOS - HHH
Nonstop2h 46mAmerican Airlines
Deal found 7/1$231
This Delta deal was found by Cheapflights users on 7/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/274:02 pmHHH - BOS
1 stop4h 33mDelta
Mon 9/85:15 amBOS - HHH
2 stops10h 07mDelta
Deal found 7/2$254
This United Airlines deal was found by Cheapflights users on 7/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/412:02 pmHHH - BOS
1 stop4h 27mUnited Airlines
Fri 9/126:00 amBOS - HHH
1 stop5h 25mUnited Airlines
Deal found 7/1$345
This Delta deal was found by Cheapflights users on 6/30. 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 8/264:02 pmHHH - ACK
1 stop19h 24mDelta
Wed 8/274:49 pmACK - HHH
1 stop18h 42mDelta
Deal found 6/30$633
This American Airlines deal was found by Cheapflights users on 6/30. 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 8/2611:19 amHHH - ACK
1 stop5h 27mAmerican Airlines
Wed 8/271:41 pmACK - HHH
2 stops21h 49mAmerican Airlines
Deal found 6/30$700

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 July 3, 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

Sat 8/9

3:41 pm-6:16 pm

Nonstop2h 35m

Boston Logan Intl

Sat 8/16

12:25 pm-3:11 pm

Nonstop2h 46m

$231

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 8/27

4:02 pm-8:35 pm

1 stop4h 33m

Boston Logan Intl

Mon 9/8

5:15 am-3:22 pm

2 stops10h 07m

$254

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 7/18

12:02 pm-5:48 pm

1 stop5h 46m

Boston Logan Intl

Tue 7/22

6:05 am-11:17 am

1 stop5h 12m

$453

Hilton Head IslandNantucket

HHH - ACK

HHHACK

Hilton Head Island

Tue 8/26

4:02 pm-11:26 am

1 stop19h 24m

Nantucket Memorial

Wed 8/27

4:49 pm-11:31 am

1 stop18h 42m

$633

Hilton Head IslandNantucket

HHH - ACK

HHHACK

Hilton Head Island

Tue 8/26

11:19 am-4:46 pm

1 stop5h 27m

Nantucket Memorial

Wed 8/27

1:41 pm-11:30 am

2 stops21h 49m

$700

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Thu 7/24

3:58 pm-9:32 pm

1 stop5h 34m

$144

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sat 7/12

3:33 pm-6:06 pm

Nonstop2h 33m

$154

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 7/9

12:02 pm-5:44 pm

1 stop5h 42m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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, January is the cheapest month in which you can book a flight from Hilton Head Island to Massachusetts (average of $218). Flying from Hilton Head Island to Massachusetts in June is currently the most expensive (average of $306). 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 July 3, 2025.

When flying from Hilton Head Island to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How much does it cost to fly round-trip from Hilton Head Island to Massachusetts?

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 July 3, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and 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.
Delta
8.0
Very good
7,982 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

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
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

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
8,861 reviews
Delta
8.0
Very good
7,982 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

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
7,982 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

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 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.

  • What are the cheapest airlines to fly from Hilton Head Island to Massachusetts one-way?

    One-way options have recently been found by users for as low as $144 on Delta. Other airlines that offer cheap prices include American Airlines from $154 and United Airlines from $164 one-way.

  • 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, January is the cheapest month in which you can book a flight from Hilton Head Island to Massachusetts (average of $218). Flying from Hilton Head Island to Massachusetts in June is currently the most expensive (average of $306). 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$256Average$423FlexibilityNo cancel feeOn-time71%

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