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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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Hilton Head Island are usually found in January or October, booked 3 days in advance, depart on a Friday or Tuesday and return on a Tuesday

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 August 14, 2025.

Round-trip from

$249
(Delta)

One-way from

$126
(Delta)

Popular in

December

Cheapest in

January

Average price

$362
From Boston Logan Intl to Hilton Head Island
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One-way flight from Boston Logan Intl to Hilton Head Island
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Highest demand for flights based on searches. 8% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. 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 9/239:05 amBOS - HHH
1 stop6h 20mDelta
Tue 9/304:05 pmHHH - BOS
1 stop5h 24mDelta
Deal found 8/14$249
This American Airlines deal was found by Cheapflights users on 8/13. 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 10/256:00 amBOS - HHH
1 stop5h 32mAmerican Airlines
Sat 11/111:16 amHHH - BOS
1 stop5h 27mAmerican Airlines
Deal found 8/13$251
This Delta deal was found by Cheapflights users on 8/14. 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 9/226:05 amBOS - HHH
2 stops9h 20mDelta
Mon 9/294:05 pmHHH - BOS
1 stop6h 15mDelta
Deal found 8/14$254
This American Airlines deal was found by Cheapflights users on 8/14. 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 11/89:18 amBOS - HHH
2 stops8h 59mAmerican Airlines
Sat 11/1512:40 pmHHH - BOS
1 stop3h 55mAmerican Airlines
Deal found 8/14$256
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/236:00 amBOS - HHH
2 stops8h 56mAmerican Airlines
Wed 10/13:26 pmHHH - BOS
2 stops7h 24mAmerican Airlines
Deal found 8/14$261
This United Airlines deal was found by Cheapflights users on 8/12. 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 9/56:00 amBOS - HHH
1 stop5h 25mUnited Airlines
Mon 9/812:06 pmHHH - BOS
2 stops6h 49mUnited Airlines
Deal found 8/12$267
This American Airlines deal was found by Cheapflights users on 8/12. 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 8/295:40 amBOS - HHH
1 stop5h 50mAmerican Airlines
Tue 9/25:28 pmHHH - BOS
1 stop4h 40mAmerican Airlines
Deal found 8/12$274
This Delta deal was found by Cheapflights users on 8/14. 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.
Fri 9/266:00 amBOS - HHH
1 stop5h 30mDelta
Mon 9/294:05 pmHHH - BOS
1 stop6h 15mDelta
Deal found 8/14$275
This American Airlines deal was found by Cheapflights users on 8/14. 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 10/166:00 amBOS - HHH
1 stop5h 32mAmerican Airlines
Wed 10/2211:16 amHHH - BOS
1 stop5h 32mAmerican Airlines
Deal found 8/14$281
This American Airlines deal was found by Cheapflights users on 8/13. 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 11/511:05 amBOS - HHH
2 stops6h 45mAmerican Airlines
Thu 11/132:51 pmHHH - BOS
2 stops7h 55mAmerican Airlines
Deal found 8/13$284

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 14, 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

Tue 9/23

9:05 am-3:25 pm

1 stop6h 20m

Hilton Head Island

Tue 9/30

4:05 pm-9:29 pm

1 stop5h 24m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 9/5

6:00 am-11:25 am

1 stop5h 25m

Hilton Head Island

Mon 9/8

12:06 pm-5:47 pm

1 stop5h 41m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 9/23

6:00 am-11:30 am

1 stop5h 30m

Hilton Head Island

Wed 10/1

4:05 pm-10:20 pm

1 stop6h 15m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 9/23

6:00 am-11:25 am

1 stop5h 25m

Hilton Head Island

Wed 10/1

11:57 am-4:22 pm

1 stop4h 25m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 10/25

6:00 am-11:32 am

1 stop5h 32m

Hilton Head Island

Sat 11/1

11:16 am-4:43 pm

1 stop5h 27m

$251

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 11/8

12:00 pm-6:17 pm

1 stop6h 17m

Hilton Head Island

Sat 11/15

12:40 pm-7:00 pm

1 stop6h 20m

$251

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 9/22

6:00 am-11:30 am

1 stop5h 30m

Hilton Head Island

Mon 9/29

4:05 pm-10:20 pm

1 stop6h 15m

$254

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 9/9

8:20 am-3:22 pm

1 stop7h 02m

$126

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 9/20

2:16 pm-6:54 pm

1 stop4h 38m

$126

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 9/10

6:00 am-11:31 am

1 stop5h 31m

$126

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 15 results
1
2

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 August 8, 2025.

The best time to book flights from Boston to Hilton Head Island is 3 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, January is the cheapest month in which you can book a flight from Boston to Hilton Head Island (average of $275). Flying from Boston to Hilton Head Island in March is currently the most expensive (average of $480). 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 14, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 57% on flights from Boston to Hilton Head Island by exploring options for tickets in the afternoon.

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 14, 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
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,916 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.2
Good
2,913 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

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

    Currently priced at $133, 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 $262, respectively. These flights start at 68% 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, January is the cheapest month in which you can book a flight from Boston to Hilton Head Island (average of $275). Flying from Boston to Hilton Head Island in March is currently the most expensive (average of $480). 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$133Average$277FlexibilityNo cancel feeOn-time62%
DeltaCheapest$167Average$399FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$262Average$430FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$638FlexibilityNo cancel feeOn-time69%

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