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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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
ago. 23 — ago. 301
sáb. 8/23
sáb. 8/30
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 agosto 18, 2025.

Round-trip from

$251
(American Airlines)

One-way from

$126
(Delta)

Popular in

October

Cheapest in

September

Average price

$316

Good one-way deal

$213 or less
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. 11% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a one-way flight from Hilton Head Island to Boston Logan Intl.
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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 agosto 18, 2025.

This American Airlines deal was found by Cheapflights users on 8/17. 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.
mar. 9/912:56 pmHHH - BOS
1 stop4h 43mAmerican Airlines
mar. 9/236:00 amBOS - HHH
1 stop4h 34mAmerican Airlines
Deal found 8/17$251
This United Airlines deal was found by Cheapflights users on 8/17. 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.
mar. 9/212:06 pmHHH - BOS
1 stop4h 22mUnited Airlines
sáb. 9/66:00 amBOS - HHH
1 stop5h 25mUnited Airlines
Deal found 8/17$266
This Delta deal was found by Cheapflights users on 8/17. 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.
vie. 9/124:05 pmHHH - BOS
1 stop6h 15mDelta
lun. 9/156:00 amBOS - HHH
1 stop5h 30mDelta
Deal found 8/17$275
This American Airlines deal was found by Cheapflights users on 8/17. 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.
sáb. 8/233:41 pmHHH - BOS
Nonstop2h 35mAmerican Airlines
sáb. 8/3012:25 pmBOS - HHH
Nonstop2h 46mAmerican Airlines
Deal found 8/17$291
This American Airlines deal was found by Cheapflights users on 8/16. 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.
vie. 9/1912:56 pmHHH - BOS
1 stop7h 29mAmerican Airlines
dom. 9/215:50 amBOS - HHH
1 stop5h 40mAmerican Airlines
Deal found 8/16$297
This Delta deal was found by Cheapflights users on 8/17. 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.
vie. 10/104:10 pmHHH - BOS
1 stop6h 10mDelta
mar. 10/146:00 amBOS - HHH
1 stop5h 27mDelta
Deal found 8/17$301
This American Airlines deal was found by Cheapflights users on 8/17. 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.
vie. 9/125:20 pmHHH - BOS
1 stop6h 24mAmerican Airlines
lun. 9/159:38 amBOS - HHH
2 stops7h 09mAmerican Airlines
Deal found 8/17$302
This Delta deal was found by Cheapflights users on 8/17. 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.
mié. 10/154:10 pmHHH - BOS
1 stop6h 10mDelta
lun. 10/206:00 amBOS - HHH
1 stop5h 37mDelta
Deal found 8/17$314

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 agosto 18, 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

mar. 9/9

12:56 pm-5:39 pm

1 stop4h 43m

Boston Logan Intl

mar. 9/23

6:00 am-10:34 am

1 stop4h 34m

$251

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

mar. 9/2

12:06 pm-4:28 pm

1 stop4h 22m

Boston Logan Intl

sáb. 9/6

6:00 am-11:25 am

1 stop5h 25m

$266

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

vie. 9/12

4:05 pm-10:20 pm

1 stop6h 15m

Boston Logan Intl

lun. 9/15

6:00 am-11:30 am

1 stop5h 30m

$275

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

vie. 10/10

4:10 pm-10:20 pm

1 stop6h 10m

Boston Logan Intl

mié. 10/15

6:00 am-11:27 am

1 stop5h 27m

$275

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

lun. 11/10

6:50 pm-12:16 am

1 stop5h 26m

Boston Logan Intl

jue. 11/13

6:40 am-10:58 am

1 stop4h 18m

$297

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

vie. 9/19

12:56 pm-8:25 pm

1 stop7h 29m

Boston Logan Intl

dom. 9/21

5:50 am-11:30 am

1 stop5h 40m

$297

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

vie. 10/10

4:10 pm-10:20 pm

1 stop6h 10m

Boston Logan Intl

mar. 10/14

6:00 am-11:27 am

1 stop5h 27m

$301

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

vie. 9/12

5:20 pm-11:44 pm

1 stop6h 24m

Boston Logan Intl

lun. 9/15

9:38 am-4:47 pm

2 stops7h 09m

$302

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

sáb. 9/6

7:24 pm-11:35 pm

1 stop4h 11m

$126

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

mié. 10/15

4:10 pm-9:27 pm

1 stop5h 17m

$126

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 16 results
1
2

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 agosto 18, 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.

How much does it cost to fly round-trip from Hilton Head Island to Boston?

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 agosto 18, 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

Entertainment

6.9

Food

6.5

Comfort

7.2

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Food

6.5

Comfort

7.2

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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 22m. The distance from Hilton Head Island to Boston is about 878 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 29% below the average price you’ll pay for this route.

  • What are the cheapest flights from Hilton Head Island to Boston?

    Looking for the cheapest flight from Hilton Head Island to Boston? While on average our users pay $283, our data indicates the cheapest price to be $213. The most popular route (Hilton Head Island - Boston Logan Intl), is priced around $251.

  • 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
Watertown
Hampton Beach
Waltham
Seabrook
Lowell
Lincoln
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Chelsea
Swansea
Saugus
Burlington
Braintree

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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 agosto 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$256Average$386FlexibilityNo cancel feeOn-time71%

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