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$119+ Cheap flights from Hilton Head Island to Boston (HHH - BOS)

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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Nov 20 — Nov 271
Thu 11/20
Thu 11/27
1 adult, Economy
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Find flight deals from Hilton Head Island to Boston

Cheapest flights from Hilton Head Island to Boston
Explore the most affordable flight options available from Hilton Head Island to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 21, 2025.

This American Airlines deal was found by Cheapflights users on 10/19. 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 12/123:27 pmHHH - BOS
1 stop7h 06mAmerican Airlines
Sun 12/1410:59 amBOS - HHH
1 stop7h 22mAmerican Airlines
Deal found 10/19$217
This American Airlines deal was found by Cheapflights users on 10/19. 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 12/127:08 pmHHH - BOS
1 stop5h 07mAmerican Airlines
Mon 12/1511:01 amBOS - HHH
2 stops7h 32mAmerican Airlines
Deal found 10/19$222
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 11/53:27 pmHHH - BOS
1 stop4h 45mAmerican Airlines
Sun 11/95:25 amBOS - HHH
1 stop6h 24mAmerican Airlines
Deal found 10/21$232
This American Airlines deal was found by Cheapflights users on 10/19. 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 10/313:32 pmHHH - BOS
1 stop6h 27mAmerican Airlines
Tue 11/41:23 pmBOS - HHH
1 stop5h 14mAmerican Airlines
Deal found 10/19$293
This American Airlines deal was found by Cheapflights users on 10/19. 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 11/15:57 pmHHH - BOS
1 stop5h 03mAmerican Airlines
Tue 11/46:30 amBOS - HHH
1 stop5h 59mAmerican Airlines
Deal found 10/19$352
This American Airlines deal was found by Cheapflights users on 10/19. 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 10/313:32 pmHHH - BOS
1 stop6h 27mAmerican Airlines
Mon 11/36:30 amBOS - HHH
1 stop5h 59mAmerican Airlines
Deal found 10/19$354

Cheap flight deals from Hilton Head Island to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to Boston (BOS). 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 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(American Airlines)

One-way from

$119
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$263
Provider with most accurate pricing for Hilton Head Island-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Hilton Head Island-Boston Logan Intl flights.
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From Hilton Head Island to Boston Logan Intl
Search Deals
One-way flight from Hilton Head Island to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Boston 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 21, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Boston that are best for you.

Fly from

Hilton Head Island

Fly to

Boston

Route

Depart

Return

Price

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 12/12

3:27 pm-10:33 pm

1 stop7h 06m

Boston Logan Intl

Sun 12/14

10:59 am-6:21 pm

1 stop7h 22m

$217

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 12/12

7:08 pm-12:15 am

1 stop5h 07m

Boston Logan Intl

Mon 12/15

11:01 am-6:33 pm

2 stops7h 32m

$222

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 11/5

3:27 pm-8:12 pm

1 stop4h 45m

Boston Logan Intl

Sun 11/9

5:25 am-11:49 am

1 stop6h 24m

$232

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 1/27

12:51 pm-10:29 pm

2 stops9h 38m

Boston Logan Intl

Thu 1/29

6:00 am-2:59 pm

2 stops8h 59m

$247

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 10/31

3:32 pm-9:59 pm

1 stop6h 27m

Boston Logan Intl

Tue 11/4

1:23 pm-6:37 pm

1 stop5h 14m

$293

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sat 11/1

5:57 pm-11:00 pm

1 stop5h 03m

Boston Logan Intl

Tue 11/4

6:30 am-12:29 pm

1 stop5h 59m

$352

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 1/20

3:29 pm-10:56 pm

2 stops7h 27m

$120

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 11/19

1:02 pm-10:22 pm

2 stops9h 20m

$124

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 4/15

12:00 pm-7:02 pm

1 stop7h 02m

$149

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sun 1/18

12:51 pm-6:22 pm

1 stop5h 31m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 13 results
1
2

Compare providers for flights from Hilton Head Island to Boston

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 Hilton Head Island to Boston in October.
ProviderPrice AccuracyTrust Score*
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 Hilton Head Island-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Hilton Head Island-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Hilton Head Island-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Hilton Head Island-Boston 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 Hilton Head Island-Boston 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 Hilton Head Island to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Hilton Head Island 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 Hilton Head Island to Boston

What is the cheapest month to book a flight from Hilton Head Island to Boston?

Currently, June is the cheapest month in which you can book a flight from Hilton Head Island to Boston (average of $37). Flying from Hilton Head Island to Boston in August is currently the most expensive (average of $73). 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 HHH to BOS?

Find hourly flight availability from Hilton Head Island to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 21, 2025.

A simple way to save on the total cost of your ticket is to fly from Hilton Head Island to Boston in the evening. If you’re flexible enough to do this you can expect to save up to 72% on your trip compared to booking a flight in the afternoon.

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated October 21, 2025.
Get a feel of what it's like to fly with American Airlines from Hilton Head Island to Boston by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,026 reviews

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,026 reviews
American Airlines
7.2
Good
11,026 reviews

Food

6.4

Overall

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Boston. 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 Hilton Head Island to Boston?

    Departing from Hilton Head Island to Boston will take you 7h 06m. The distance from Hilton Head Island to Boston is about 878 mi.

  • What is the cheapest airline to fly from Hilton Head Island to Boston round-trip?

    Our cheapest airline available from Hilton Head Island to Boston is American Airlines. Our recent data shows that you can find tickets from as low as $250 on this airline. American Airlines is currently priced 23% below the average price you’ll pay for this route.

  • Can I find deals for flights from Hilton Head Island to Boston that include hotel bookings?

    Yes. In addition to deals on Hilton Head Island to Boston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hilton Head Island to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Boston.

  • Can I find deals for business class flights from Hilton Head Island to Boston?

    Yes. Cheapflights offers flight deals from Hilton Head Island to Boston 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 Hilton Head Island to Boston?

    Currently, June is the cheapest month in which you can book a flight from Hilton Head Island to Boston (average of $37). Flying from Hilton Head Island to Boston in August is currently the most expensive (average of $73). 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 Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Top airline flying from Hilton Head Island to Boston

Discover the top airline that operate flights from Hilton Head Island to Boston. 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 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$250Average$368FlexibilityNo cancel feeOn-time71%

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