HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Hilton Head Island

$151+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Sep 3 — Sep 101
Thu 9/3
Thu 9/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston to Hilton Head Island with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 4, 2026.

This American Airlines deal was found by Cheapflights users on 8/1. 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 9/510:09 am
BOS
-
HHH
Nonstop2h 51m
American Airlines
Sat 9/125:15 pm
HHH
-
BOS
1 stop5h 09m
American Airlines
Deal found 8/1$311
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Thu 9/106:00 am
BOS
-
HHH
1 stop8h 03m
United Airlines
Wed 9/162:48 pm
HHH
-
BOS
1 stop7h 11m
United Airlines
Deal found 7/31$319
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Wed 10/76:00 am
BOS
-
HHH
1 stop5h 05m
American Airlines
Tue 10/1312:29 pm
HHH
-
BOS
1 stop5h 27m
American Airlines
Deal found 7/30$321
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Thu 9/105:45 am
BOS
-
HHH
2 stops8h 18m
United Airlines
Thu 9/172:48 pm
HHH
-
BOS
1 stop8h 42m
United Airlines
Deal found 7/31$324
This Delta deal was found by Cheapflights users on 8/2. 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.
Thu 9/106:05 am
BOS
-
HHH
2 stops9h 22m
Delta
Wed 9/164:17 pm
HHH
-
BOS
1 stop6h 09m
Delta
Deal found 8/2$326
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:45 am
BOS
-
HHH
2 stops8h 18m
United Airlines
Fri 8/282:58 pm
HHH
-
BOS
2 stops9h 01m
United Airlines
Deal found 7/30$329
This Delta deal was found by Cheapflights users on 8/2. 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.
Thu 9/109:05 am
BOS
-
HHH
1 stop6h 22m
Delta
Mon 9/144:17 pm
HHH
-
BOS
1 stop6h 09m
Delta
Deal found 8/2$330
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Wed 8/197:05 am
BOS
-
HHH
1 stop6h 58m
United Airlines
Mon 8/242:58 pm
HHH
-
BOS
1 stop8h 36m
United Airlines
Deal found 8/1$334
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Sat 9/56:00 am
BOS
-
HHH
1 stop7h 14m
United Airlines
Sat 9/122:48 pm
HHH
-
BOS
1 stop7h 11m
United Airlines
Deal found 8/1$338
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Wed 8/195:45 am
BOS
-
HHH
2 stops8h 18m
United Airlines
Wed 8/262:58 pm
HHH
-
BOS
1 stop7h 01m
United Airlines
Deal found 7/31$339

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 August 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(American Airlines)

One-way from

$151
(American Airlines)

Popular in

April

Cheapest in

December

Average price

$392

Good round-trip deal

$392 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. 14% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 4, 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

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 9/10

8:00 am-3:27 pm

2 stops7h 27m

Hilton Head Island

Wed 9/16

12:17 pm-9:25 pm

2 stops9h 08m

$331

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 8/19

5:45 am-2:03 pm

2 stops8h 18m

Hilton Head Island

Mon 8/24

2:58 pm-9:59 pm

1 stop7h 01m

$339

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 10/7

7:00 am-11:43 am

1 stop4h 43m

Hilton Head Island

Tue 10/13

12:23 pm-11:59 pm

2 stops11h 36m

$339

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 10/30

6:00 am-11:43 am

1 stop5h 43m

Hilton Head Island

Mon 11/2

12:23 pm-11:59 pm

2 stops11h 36m

$344

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 9/10

5:40 am-3:27 pm

2 stops9h 47m

Hilton Head Island

Mon 9/14

12:17 pm-10:26 pm

2 stops10h 09m

$385

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 9/6

7:05 am-2:03 pm

1 stop6h 58m

Hilton Head Island

Wed 9/9

2:48 pm-11:30 pm

1 stop8h 42m

$401

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 8/29

5:45 am-2:03 pm

2 stops8h 18m

Hilton Head Island

Wed 9/2

2:58 pm-11:59 pm

2 stops9h 01m

$409

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 9/5

6:05 am-3:32 pm

2 stops9h 27m

Hilton Head Island

Sat 9/12

12:17 pm-11:58 pm

2 stops11h 41m

$414
Quickest round-trip

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 9/16

6:00 am-12:15 pm

2 stops6h 15m

Hilton Head Island

Sat 9/19

2:20 pm-9:49 pm

2 stops7h 29m

$478
Cheapest one-way

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 8/30

6:01 am-2:03 pm

1 stop8h 02m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 19 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 August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust 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 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?

The best time to book flights from Boston to Hilton Head Island is 65 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 $574). 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 August 4, 2026.

When flying from Boston to Hilton Head Island, 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 Boston to Hilton Head Island?

Airfare is typical for this route at the moment.

Boston to Hilton Head Island flights typically cost between $289 and $521 in September.
The cheapest round-trip price found within the last 5 days was $311 on American Airlines (Sep 5-Sep 12).

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 August 4, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andJetBlue 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
7.8
Good
8,483 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.8

Overall

7.8

Reviews

1 / 20
6.0
Good

Cidalia,Aug 2023

BOS - MIA

I like Delta overall but the delays lately without justification are not leaving a good impression. Both flights were delayed for over 2 hours
Delta
7.8
Good
8,483 reviews
Delta
7.8
Good
8,483 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.8

Overall

7.8

Reviews

1 / 20
6.0
Good

Cidalia,Aug 2023

BOS - MIA

I like Delta overall but the delays lately without justification are not leaving a good impression. Both flights were delayed for over 2 hours
United Airlines
7.4
Good
10,060 reviews
Delta
7.8
Good
8,483 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.8

Overall

7.8

Reviews

1 / 20
6.0
Good

Cidalia,Aug 2023

BOS - MIA

I like Delta overall but the delays lately without justification are not leaving a good impression. Both flights were delayed for over 2 hours
JetBlue
7.2
Good
3,026 reviews
Delta
7.8
Good
8,483 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.8

Overall

7.8

Reviews

1 / 20
6.0
Good

Cidalia,Aug 2023

BOS - MIA

I like Delta overall but the delays lately without justification are not leaving a good impression. Both flights were delayed for over 2 hours
American Airlines
7.1
Good
11,845 reviews
Delta
7.8
Good
8,483 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Food

7.2

Comfort

7.8

Overall

7.8

Reviews

1 / 20
6.0
Good

Cidalia,Aug 2023

BOS - MIA

I like Delta overall but the delays lately without justification are not leaving a good impression. Both flights were delayed for over 2 hours

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 7h 27m. Your travel time can differ by up to 51m. 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 JetBlue - these airlines can fly you to your destination from $183 and $212, respectively. These flights start at 61% 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 $420 for a flight from Boston to Hilton Head Island. The cheapest flight overall is $289 while the most popular route, (Boston Logan Intl - Hilton Head Island) is currently priced at $321.

  • 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 $574). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 August 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$148Average$363FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$183Average$375FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$212Average$387FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$251Average$414FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.