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Hilton Head Island

$126+ Cheap flights from Boston to Hilton Head Island (BOS - 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Hilton Head Island are usually found in December or November, booked 46 days in advance, depart on a Friday or Tuesday and return on a Tuesday

Cheap flight deals from Boston to Hilton Head Island

Cheapest flights from Boston to Hilton Head Island
Explore the most affordable flight options available from Boston to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2012:17 pmBOS - HHH
1 stop5h 26mAmerican Airlines
Wed 12/242:46 pmHHH - BOS
1 stop6h 25mAmerican Airlines
Deal found 12/16$402
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:55 amBOS - HHH
1 stop6h 48mAmerican Airlines
Tue 1/612:51 pmHHH - BOS
1 stop5h 28mAmerican Airlines
Deal found 12/16$405
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:55 amBOS - HHH
1 stop6h 48mAmerican Airlines
Mon 1/52:46 pmHHH - BOS
1 stop4h 32mAmerican Airlines
Deal found 12/16$412
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:40 amBOS - HHH
1 stop4h 19mAmerican Airlines
Wed 12/242:46 pmHHH - BOS
1 stop6h 25mAmerican Airlines
Deal found 12/16$467
This American Airlines deal was found by Cheapflights users on 12/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/239:00 amBOS - HHH
2 stops8h 43mAmerican Airlines
Sat 12/276:13 pmHHH - BOS
1 stop4h 24mAmerican Airlines
Deal found 12/17$508
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:59 amBOS - HHH
2 stops8h 17mAmerican Airlines
Tue 1/63:29 pmHHH - BOS
1 stop6h 53mAmerican Airlines
Deal found 12/16$522

Find flight deals from Boston to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Hilton Head Island (HHH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$251
(American Airlines)

One-way from

$126
(American Airlines)

Popular in

February

Cheapest in

December

Average price

$292
Provider with most accurate pricing for Boston Logan Intl-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Hilton Head Island flights.
Search Deals
From Boston Logan Intl to Hilton Head Island
Search Deals
One-way flight from Boston Logan Intl to Hilton Head Island
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston 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 December 18, 2025.
Use the filters below to find and compare flights from Boston to Hilton Head Island that are best for you.

Fly from

Boston

Fly to

Hilton Head Island

Route

Depart

Return

Price

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 1/11

8:03 pm-12:20 pm

2 stops16h 17m

Hilton Head Island

Sat 1/17

3:29 pm-10:22 pm

1 stop6h 53m

$253

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 2/11

7:00 am-2:59 pm

2 stops7h 59m

Hilton Head Island

Sat 2/14

11:02 am-3:30 pm

1 stop4h 28m

$256

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 1/15

8:30 am-2:59 pm

1 stop6h 29m

Hilton Head Island

Sat 1/17

3:29 pm-10:22 pm

1 stop6h 53m

$264

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 1/4

5:53 am-10:44 am

1 stop4h 51m

Hilton Head Island

Wed 1/7

3:29 pm-7:12 am

2 stops15h 43m

$266

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

8:03 pm-12:20 pm

2 stops16h 17m

Hilton Head Island

Sun 2/15

11:02 am-8:33 pm

2 stops9h 31m

$275

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 5/29

6:00 am-11:23 am

1 stop5h 23m

Hilton Head Island

Fri 6/5

4:00 pm-10:27 pm

1 stop6h 27m

$277

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 1/1

10:50 am-5:43 pm

2 stops6h 53m

Hilton Head Island

Mon 1/5

2:46 pm-7:18 pm

1 stop4h 32m

$282

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 2/17

7:45 am-3:05 pm

2 stops7h 20m

$131

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 6/15

8:00 am-2:01 pm

1 stop6h 01m

$149

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 6/16

6:00 am-11:23 am

1 stop5h 23m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 15 results
1
2

Compare providers for flights from Boston to Hilton Head Island

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Hilton Head Island in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Boston-Hilton Head Island flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Boston-Hilton Head Island flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Boston-Hilton Head Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Hilton Head Island flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

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

How far ahead should I book a flight from Boston to Hilton Head Island?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Hilton Head Island. Price data was last updated on December 12, 2025.

The best time to book flights from Boston to Hilton Head Island is 25 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, August is the cheapest month in which you can book a flight from Boston to Hilton Head Island (average of $43). Flying from Boston to Hilton Head Island in November is currently the most expensive (average of $84). 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 BOS to HHH?

Find hourly flight availability from Boston 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 December 18, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 77% on flights from Boston to Hilton Head Island by exploring options for tickets in the evening.

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 December 18, 2025.
Get a feel of what it's like to fly with Delta, American Airlines, and JetBlue from Boston to Hilton Head Island by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,008 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,055 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,897 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Boston 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.

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

    American Airlines can get you from Boston to Hilton Head Island in just under 16h 17m. Your travel time can differ by up to . There are 878 mi between Boston and Hilton Head Island.

  • What are the cheapest airlines flying from Boston to Hilton Head Island round-trip?

    Currently priced at $88, JetBlue will fly you from Boston to Hilton Head Island and back. In addition to JetBlue, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and American Airlines - these airlines can fly you to your destination from $217 and $256, respectively. These flights start at 75% lower than the current average price 3 months from now.

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

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

  • How can I find direct flights from Boston 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 Boston to Hilton Head Island.

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

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

    Currently, August is the cheapest month in which you can book a flight from Boston to Hilton Head Island (average of $43). Flying from Boston to Hilton Head Island in November is currently the most expensive (average of $84). 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 Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
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Top 3 airlines flying from Boston to Hilton Head Island

Discover the top 3 airlines that operate flights from Boston 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$167Average$236FlexibilityNo cancel feeOn-time62%
DeltaCheapest$217Average$399FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$256Average$386FlexibilityNo cancel feeOn-time71%

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