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Hilton Head Island

$116+ 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 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
May 19 — May 261
Tue 5/19
Tue 5/26
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 April 19, 2026.

This Delta deal was found by Cheapflights users on 4/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:00 am
BOS
-
HHH
1 stop7h 33m
Delta
Wed 6/104:12 pm
HHH
-
BOS
1 stop7h 15m
Delta
Deal found 4/18$231
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Sat 7/412:43 pm
BOS
-
HHH
Nonstop2h 51m
American Airlines
Tue 7/72:48 pm
HHH
-
BOS
1 stop6h 12m
American Airlines
Deal found 4/18$237
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:30 am
BOS
-
HHH
1 stop6h 50m
Delta
Fri 5/84:16 pm
HHH
-
BOS
1 stop6h 09m
Delta
Deal found 4/17$241
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:30 am
BOS
-
HHH
2 stops9h 50m
Delta
Tue 5/124:16 pm
HHH
-
BOS
1 stop6h 09m
Delta
Deal found 4/17$246
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:30 am
BOS
-
HHH
1 stop6h 50m
Delta
Tue 5/124:16 pm
HHH
-
BOS
1 stop6h 09m
Delta
Deal found 4/17$256
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:00 am
BOS
-
HHH
1 stop7h 29m
Delta
Fri 7/244:12 pm
HHH
-
BOS
1 stop7h 19m
Delta
Deal found 4/16$257
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:00 am
BOS
-
HHH
1 stop7h 29m
Delta
Wed 7/2212:11 pm
HHH
-
BOS
2 stops10h 57m
Delta
Deal found 4/16$262
This American Airlines deal was found by Cheapflights users on 4/15. 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 6/1312:10 pm
BOS
-
HHH
Nonstop2h 59m
American Airlines
Tue 6/165:21 pm
HHH
-
BOS
1 stop7h 19m
American Airlines
Deal found 4/15$274
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am
BOS
-
HHH
1 stop5h 23m
Delta
Mon 9/144:00 pm
HHH
-
BOS
1 stop7h 22m
Delta
Deal found 4/17$280

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 April 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$231
(Delta)

One-way from

$116
(Delta)

Popular in

April

Cheapest in

December

Average price

$573

Good round-trip deal

$194 or less
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. 18% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Hilton Head Island.
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 April 19, 2026.
Use the filters below to find and compare flights from Boston to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 5/6

9:30 am-3:20 pm

1 stop5h 50m

Hilton Head Island

Tue 5/12

4:16 pm-9:33 pm

1 stop5h 17m

$329

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 7/20

1:00 pm-11:29 am

1 stop22h 29m

Hilton Head Island

Fri 7/24

12:11 pm-11:08 pm

2 stops10h 57m

$351

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 5/9

7:30 am-2:11 pm

1 stop6h 41m

Hilton Head Island

Wed 5/13

3:08 pm-9:59 pm

1 stop6h 51m

$423

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 5/25

8:00 am-3:33 pm

1 stop7h 33m

Hilton Head Island

Thu 5/28

4:16 pm-10:25 pm

1 stop6h 09m

$434

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 5/20

7:00 am-3:33 pm

2 stops8h 33m

Hilton Head Island

Sat 5/23

12:18 pm-11:29 pm

2 stops11h 11m

$518

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 5/8

5:45 am-3:41 pm

2 stops9h 56m

Hilton Head Island

Mon 5/11

3:08 pm-11:59 pm

2 stops8h 51m

$538

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 4/30

7:30 am-2:11 pm

1 stop6h 41m

Hilton Head Island

Mon 5/4

3:08 pm-11:35 pm

1 stop8h 27m

$559
Cheapest one-way
Quickest one-way

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 7/16

6:00 am-11:29 am

1 stop5h 29m

$116

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 7/15

5:40 am-3:29 pm

2 stops9h 49m

$121

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 6/16

6:00 am-11:31 am

1 stop5h 31m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 12 resultsSorted by cheapest first
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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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 FlightHub the most. FlightHub 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 April 17, 2026.

The best time to book flights from Boston to Hilton Head Island is 66 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, December is the cheapest month in which you can book a flight from Boston to Hilton Head Island (average of $292). Flying from Boston to Hilton Head Island in April is currently the most expensive (average of $567). 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.

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

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 April 19, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican 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
8,422 reviews

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Overall

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
8,422 reviews
Delta
7.9
Good
8,422 reviews

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Overall

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
9,604 reviews
Delta
7.9
Good
8,422 reviews

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Overall

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
7.1
Good
11,620 reviews
Delta
7.9
Good
8,422 reviews

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Overall

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?

    Delta and United Airlines can get you from Boston to Hilton Head Island in just under 5h 50m. Your travel time can differ by up to 2h 36m. There are 878 mi between Boston and Hilton Head Island. This flight may include one or multiple stops.

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

    Currently priced at $148, Delta will fly you from Boston to Hilton Head Island and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and American Airlines - these airlines can fly you to your destination from $183 and $263, respectively. These flights start at 60% lower than the current average price 3 months from now.

  • What are the cheapest flights from Boston to Hilton Head Island?

    On average you can expect to pay $574 for a flight from Boston to Hilton Head Island. The cheapest flight overall is $333 while the most popular route, (Boston Logan Intl - Hilton Head Island) is currently priced at $246.

  • 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, December is the cheapest month in which you can book a flight from Boston to Hilton Head Island (average of $292). Flying from Boston to Hilton Head Island in April is currently the most expensive (average of $567). 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 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 April 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$148Average$362FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$183Average$433FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$263Average$398FlexibilityNo cancel feeOn-time71%

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