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Hilton Head Island

$115+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
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 January, booked 46 days in advance, depart on a Friday or Tuesday and return on a Tuesday

Find 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 October 23, 2025.

This American Airlines deal was found by Cheapflights users on 10/21. 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.
Fri 12/51:28 pmBOS - HHH
1 stop5h 05mAmerican Airlines
Fri 12/123:27 pmHHH - BOS
1 stop7h 06mAmerican Airlines
Deal found 10/21$217
This American Airlines deal was found by Cheapflights users on 10/22. 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 11/157:30 amBOS - HHH
1 stop4h 36mAmerican Airlines
Mon 11/177:07 pmHHH - BOS
1 stop5h 09mAmerican Airlines
Deal found 10/22$247
This American Airlines deal was found by Cheapflights users on 10/22. 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 11/1211:05 amBOS - HHH
2 stops7h 32mAmerican Airlines
Fri 11/143:27 pmHHH - BOS
2 stops7h 20mAmerican Airlines
Deal found 10/22$262
This American Airlines deal was found by Cheapflights users on 10/22. 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 11/56:00 amBOS - HHH
1 stop4h 58mAmerican Airlines
Sat 11/812:38 pmHHH - BOS
1 stop6h 22mAmerican Airlines
Deal found 10/22$278
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/275:25 amBOS - HHH
1 stop4h 59mAmerican Airlines
Thu 12/42:17 pmHHH - BOS
2 stops7h 59mAmerican Airlines
Deal found 10/21$283
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/1811:10 amBOS - HHH
1 stop7h 27mAmerican Airlines
Sat 11/2212:38 pmHHH - BOS
1 stop4h 00mAmerican Airlines
Deal found 10/23$288
This American Airlines deal was found by Cheapflights users on 10/21. 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 10/298:00 amBOS - HHH
1 stop7h 02mAmerican Airlines
Fri 10/313:32 pmHHH - BOS
1 stop6h 27mAmerican Airlines
Deal found 10/21$308
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/810:59 amBOS - HHH
1 stop7h 18mAmerican Airlines
Wed 11/123:27 pmHHH - BOS
1 stop6h 53mAmerican Airlines
Deal found 10/23$312

Cheap 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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(American Airlines)

One-way from

$115
(American Airlines)

Popular in

February

Cheapest in

December

Average price

$342
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 ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 23, 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

Fri 12/5

1:28 pm-6:33 pm

1 stop5h 05m

Hilton Head Island

Fri 12/12

3:27 pm-10:33 pm

1 stop7h 06m

$217

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 11/15

12:11 pm-6:17 pm

1 stop6h 06m

Hilton Head Island

Mon 11/17

7:07 pm-12:16 am

1 stop5h 09m

$247

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 12/12

6:30 am-12:22 pm

1 stop5h 52m

Hilton Head Island

Sun 12/14

12:21 pm-4:55 pm

1 stop4h 34m

$247

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 11/12

11:10 am-6:37 pm

1 stop7h 27m

Hilton Head Island

Fri 11/14

7:07 pm-12:16 am

1 stop5h 09m

$252

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 11/27

5:25 am-10:24 am

1 stop4h 59m

Hilton Head Island

Thu 12/4

11:30 am-5:24 pm

1 stop5h 54m

$278

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 11/5

6:00 am-10:58 am

1 stop4h 58m

Hilton Head Island

Sat 11/8

12:38 pm-7:00 pm

1 stop6h 22m

$278

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 11/18

11:05 am-6:37 pm

2 stops7h 32m

Hilton Head Island

Sat 11/22

12:38 pm-4:38 pm

1 stop4h 00m

$293

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 12/2

1:23 pm-6:37 pm

1 stop5h 14m

$119

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 12/16

6:40 am-10:59 am

1 stop4h 19m

$119

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 1/21

6:00 am-2:59 pm

2 stops8h 59m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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 October 17, 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 October is currently the most expensive (average of $82). 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 October 23, 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 October 23, 2025.
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
7,982 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,982 reviews
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,995 reviews
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,033 reviews
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
JetBlue
7.2
Good
2,908 reviews
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

7.9

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 05m. 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 American Airlines - these airlines can fly you to your destination from $167 and $255, 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 October is currently the most expensive (average of $82). 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
Bluffton

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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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$167Average$236FlexibilityNo cancel feeOn-time62%
DeltaCheapest$167Average$362FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$255Average$396FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$614FlexibilityNo cancel feeOn-time69%

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