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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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 August, 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 September 16, 2025.

Round-trip from

$248
(American Airlines)

One-way from

$126
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$356
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. 7% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/306:00 amBOS - HHH
1 stop4h 46mAmerican Airlines
Thu 11/611:28 amHHH - BOS
1 stop5h 56mAmerican Airlines
Deal found 9/15$248
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 11/66:00 amBOS - HHH
1 stop4h 58mAmerican Airlines
Mon 11/103:27 pmHHH - BOS
2 stops7h 20mAmerican Airlines
Deal found 9/15$254
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 9/226:00 amBOS - HHH
1 stop5h 30mDelta
Mon 9/294:05 pmHHH - BOS
1 stop6h 15mDelta
Deal found 9/16$273
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 10/2110:35 amBOS - HHH
1 stop6h 16mAmerican Airlines
Sat 10/253:02 pmHHH - BOS
1 stop4h 42mAmerican Airlines
Deal found 9/15$274
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Mon 10/206:00 amBOS - HHH
1 stop5h 32mAmerican Airlines
Sat 10/253:02 pmHHH - BOS
1 stop6h 16mAmerican Airlines
Deal found 9/15$299
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 12/248:00 amBOS - HHH
2 stops6h 16mAmerican Airlines
Tue 12/306:13 pmHHH - BOS
1 stop4h 24mAmerican Airlines
Deal found 9/14$304

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 September 16, 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

Thu 11/6

6:00 am-10:58 am

1 stop4h 58m

Hilton Head Island

Mon 11/10

3:27 pm-10:47 pm

2 stops7h 20m

$254

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 10/21

12:03 pm-4:51 pm

1 stop4h 48m

Hilton Head Island

Sat 10/25

3:02 pm-7:44 pm

1 stop4h 42m

$274

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 10/20

6:00 am-11:32 am

1 stop5h 32m

Hilton Head Island

Sat 10/25

3:02 pm-9:18 pm

1 stop6h 16m

$299

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 12/24

8:00 am-2:16 pm

2 stops6h 16m

Hilton Head Island

Tue 12/30

6:13 pm-10:37 pm

1 stop4h 24m

$304

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 9/29

6:00 am-11:16 am

1 stop5h 16m

Hilton Head Island

Fri 10/3

11:57 am-5:54 pm

1 stop5h 57m

$307

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

10:30 am-5:34 pm

1 stop7h 04m

Hilton Head Island

Sun 2/15

6:15 pm-10:27 pm

1 stop4h 12m

$324

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 10/20

6:00 am-11:37 am

1 stop5h 37m

Hilton Head Island

Wed 10/22

4:10 pm-9:27 pm

1 stop5h 17m

$325

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 11/22

6:00 am-12:06 pm

1 stop6h 06m

Hilton Head Island

Sat 12/6

2:17 pm-11:15 pm

2 stops8h 58m

$329

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 10/14

6:00 am-11:16 am

1 stop5h 16m

$126

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 10/15

8:00 am-3:30 pm

1 stop7h 30m

$126

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 16 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 September 12, 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 $479). 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 September 16, 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 September 16, 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
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

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
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

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
8,924 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

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
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

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
2,914 reviews
Delta
8.0
Very good
7,957 reviews

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Crew

8.5

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.

  • 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 4h 58m. 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 $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 $256, respectively. These flights start at 66% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Boston to Hilton Head Island one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $126. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Boston to Hilton Head Island for a low price.

  • 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 $479). 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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Alternative routes for Boston to Hilton Head Island

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$133Average$277FlexibilityNo cancel feeOn-time62%
DeltaCheapest$167Average$399FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$256Average$405FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$638FlexibilityNo cancel feeOn-time69%

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