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$126+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$283
(American Airlines)

One-way from

$126
(Delta)

Popular in

October

Cheapest in

September

Average price

$217
From Hilton Head Island to Boston Logan Intl
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One-way flight from Hilton Head Island to Boston Logan Intl
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Highest demand for flights based on searches. 13% potential increase in price ($58 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($22 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 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 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.
Tue 9/3012:56 pmHHH - BOS
1 stop4h 43mAmerican Airlines
Sat 10/42:16 pmBOS - HHH
1 stop4h 38mAmerican Airlines
Deal found 9/15$283
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2512:19 pmHHH - BOS
1 stop7h 29mAmerican Airlines
Thu 11/276:00 amBOS - HHH
1 stop5h 02mAmerican Airlines
Deal found 9/16$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.
Mon 9/295:20 pmHHH - BOS
1 stop6h 24mAmerican Airlines
Fri 10/37:28 amBOS - HHH
2 stops9h 19mAmerican Airlines
Deal found 9/14$312
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/811:57 amHHH - BOS
1 stop4h 25mUnited Airlines
Sun 10/126:00 amBOS - HHH
1 stop5h 20mUnited Airlines
Deal found 9/15$319
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/294:05 pmHHH - BOS
1 stop4h 20mDelta
Fri 10/38:05 amBOS - HHH
1 stop7h 20mDelta
Deal found 9/14$487
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3012:14 pmHHH - BOS
1 stop6h 17mDelta
Sat 10/49:05 amBOS - HHH
1 stop6h 20mDelta
Deal found 9/15$539

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 September 16, 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

Tue 9/30

12:56 pm-5:39 pm

1 stop4h 43m

Boston Logan Intl

Sat 10/4

2:16 pm-6:54 pm

1 stop4h 38m

$283

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 11/25

12:19 pm-7:48 pm

1 stop7h 29m

Boston Logan Intl

Thu 11/27

6:00 am-11:02 am

1 stop5h 02m

$299

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Mon 9/29

5:20 pm-11:44 pm

1 stop6h 24m

Boston Logan Intl

Fri 10/3

7:28 am-4:47 pm

2 stops9h 19m

$312

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 10/8

11:57 am-4:22 pm

1 stop4h 25m

Boston Logan Intl

Sun 10/12

6:00 am-11:20 am

1 stop5h 20m

$319

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Thu 10/9

11:57 am-4:22 pm

1 stop4h 25m

Boston Logan Intl

Mon 10/13

6:00 am-11:16 am

1 stop5h 16m

$319

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Mon 9/29

4:05 pm-8:25 pm

1 stop4h 20m

Boston Logan Intl

Fri 10/3

8:05 am-3:25 pm

1 stop7h 20m

$487

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 9/30

12:14 pm-6:31 pm

1 stop6h 17m

Boston Logan Intl

Sat 10/4

9:05 am-3:25 pm

1 stop6h 20m

$539

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 10/15

4:10 pm-9:27 pm

1 stop5h 17m

$126

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 10/15

3:32 pm-7:55 pm

1 stop4h 23m

$126

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 10/22

12:17 pm-4:57 pm

1 stop4h 40m

$126

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 17 results
1
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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, January is the cheapest month in which you can book a flight from Hilton Head Island to Boston (average of $218). Flying from Hilton Head Island to Boston in July is currently the most expensive (average of $311). 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 September 16, 2025.

A simple way to save on the total cost of your ticket is to fly from Hilton Head Island to Boston in the morning. If you’re flexible enough to do this you can expect to save up to 4% on your trip compared to booking a flight at noon.

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 September 16, 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
10,000 reviews

Comfort

7.2

Food

6.4

Crew

8.0

Boarding

7.5

Overall

7.2

Entertainment

6.9

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Food

6.4

Crew

8.0

Boarding

7.5

Overall

7.2

Entertainment

6.9

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 4h 43m. 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 $256 on this airline. American Airlines is currently priced 30% 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, January is the cheapest month in which you can book a flight from Hilton Head Island to Boston (average of $218). Flying from Hilton Head Island to Boston in July is currently the most expensive (average of $311). 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
Chelsea
Warwick
Peabody
Quincy
York Beach
Swansea
Old Orchard Beach
Brockton
Waltham

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$256Average$386FlexibilityNo cancel feeOn-time71%

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