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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
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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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 January 20, 2026.

This American Airlines deal was found by Cheapflights users on 1/17. 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.
Wed 2/116:39 am
BOS
-
HHH
1 stop5h 41m
American Airlines
Sat 2/142:58 pm
HHH
-
BOS
1 stop6h 52m
American Airlines
Deal found 1/17$251
This American Airlines deal was found by Cheapflights users on 1/18. 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 2/118:30 am
BOS
-
HHH
1 stop6h 29m
American Airlines
Mon 2/164:11 pm
HHH
-
BOS
1 stop6h 11m
American Airlines
Deal found 1/18$274
This Delta deal was found by Cheapflights users on 1/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:00 am
BOS
-
HHH
1 stop5h 23m
Delta
Thu 8/204:00 pm
HHH
-
BOS
1 stop6h 27m
Delta
Deal found 1/19$277
This American Airlines deal was found by Cheapflights users on 1/18. 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 2/197:40 am
BOS
-
HHH
1 stop6h 42m
American Airlines
Sun 2/224:11 pm
HHH
-
BOS
1 stop6h 11m
American Airlines
Deal found 1/18$287
This American Airlines deal was found by Cheapflights users on 1/19. 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.
Tue 2/36:00 am
BOS
-
HHH
2 stops8h 59m
American Airlines
Sat 2/712:54 pm
HHH
-
BOS
2 stops7h 19m
American Airlines
Deal found 1/19$288
This American Airlines deal was found by Cheapflights users on 1/18. 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 2/227:15 am
BOS
-
HHH
2 stops7h 07m
American Airlines
Thu 2/264:11 pm
HHH
-
BOS
1 stop6h 11m
American Airlines
Deal found 1/18$292
This American Airlines deal was found by Cheapflights users on 1/18. 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 8/246:00 am
BOS
-
HHH
1 stop4h 48m
American Airlines
Mon 8/316:15 pm
HHH
-
BOS
1 stop4h 20m
American Airlines
Deal found 1/18$297
This Delta deal was found by Cheapflights users on 1/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:00 am
BOS
-
HHH
1 stop5h 23m
Delta
Tue 8/1812:00 pm
HHH
-
BOS
2 stops10h 27m
Delta
Deal found 1/19$302

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 January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$251
(American Airlines)

One-way from

$126
(American Airlines)

Popular in

February

Cheapest in

December

Average price

$364
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. 8% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 20, 2026.
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

Tue 2/3

6:43 am-12:20 pm

1 stop5h 37m

Hilton Head Island

Sat 2/7

3:29 pm-8:33 pm

1 stop5h 04m

$277

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 2/27

9:00 am-3:41 pm

1 stop6h 41m

Hilton Head Island

Mon 3/2

2:58 pm-9:50 pm

1 stop6h 52m

$277

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 3/5

8:00 am-3:41 pm

1 stop7h 41m

Hilton Head Island

Mon 3/9

4:11 pm-10:22 pm

1 stop6h 11m

$277

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 2/6

6:00 am-2:59 pm

2 stops8h 59m

Hilton Head Island

Mon 2/9

3:29 pm-10:22 pm

1 stop6h 53m

$282

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

8:30 am-2:59 pm

1 stop6h 29m

Hilton Head Island

Sun 2/15

2:58 pm-10:24 pm

2 stops7h 26m

$282

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 2/19

8:00 am-3:41 pm

1 stop7h 41m

Hilton Head Island

Thu 2/26

2:58 pm-10:48 pm

2 stops7h 50m

$282

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/2

6:00 am-2:59 pm

2 stops8h 59m

Hilton Head Island

Thu 2/5

12:51 pm-8:11 pm

2 stops7h 20m

$288

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 4/15

6:00 am-2:06 pm

1 stop8h 06m

$149

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 3/5

9:00 am-3:41 pm

1 stop6h 41m

$149

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 4/15

6:00 am-11:18 am

1 stop5h 18m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Hilton Head Island flight deals on Cheapflights vs. FlightHub >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 Expedia the most. Expedia 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 January 16, 2026.

The best time to book flights from Boston to Hilton Head Island is 15 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.

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 January 20, 2026.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines 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
8,080 reviews

Overall

7.9

Crew

8.5

Food

7.2

Entertainment

7.8

Boarding

8.1

Comfort

7.9

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
8,080 reviews
Delta
7.9
Good
8,080 reviews

Overall

7.9

Crew

8.5

Food

7.2

Entertainment

7.8

Boarding

8.1

Comfort

7.9

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.
United Airlines
7.4
Good
9,183 reviews
Delta
7.9
Good
8,080 reviews

Overall

7.9

Crew

8.5

Food

7.2

Entertainment

7.8

Boarding

8.1

Comfort

7.9

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
11,166 reviews
Delta
7.9
Good
8,080 reviews

Overall

7.9

Crew

8.5

Food

7.2

Entertainment

7.8

Boarding

8.1

Comfort

7.9

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
2,892 reviews
Delta
7.9
Good
8,080 reviews

Overall

7.9

Crew

8.5

Food

7.2

Entertainment

7.8

Boarding

8.1

Comfort

7.9

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 5h 37m. 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 $167, 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 United Airlines - these airlines can fly you to your destination from $167 and $183, respectively. These flights start at 53% 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
Beaufort

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Top 4 airlines flying from Boston to Hilton Head Island

Discover the top 4 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 January 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$167Average$277FlexibilityNo cancel feeOn-time62%
DeltaCheapest$167Average$352FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$183Average$405FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$387FlexibilityNo cancel feeOn-time71%

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