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$179+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Apr 19 — Apr 261
Sun 4/19
Sun 4/26
1 adult, Economy
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Cheap 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 March 20, 2026.

This United Airlines deal was found by Cheapflights users on 3/17. 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.
Wed 4/14:11 pm
HHH
-
BOS
1 stop5h 43m
United Airlines
Tue 4/77:15 am
BOS
-
HHH
1 stop7h 01m
United Airlines
Deal found 3/17$334
This United Airlines deal was found by Cheapflights users on 3/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/13:05 pm
HHH
-
BOS
1 stop6h 54m
United Airlines
Sun 4/56:00 am
BOS
-
HHH
1 stop8h 16m
United Airlines
Deal found 3/16$339
This Delta deal was found by Cheapflights users on 3/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/224:16 pm
HHH
-
BOS
1 stop6h 09m
Delta
Mon 5/256:00 am
BOS
-
HHH
1 stop5h 37m
Delta
Deal found 3/19$357
This Delta deal was found by Cheapflights users on 3/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:16 pm
HHH
-
BOS
1 stop6h 09m
Delta
Mon 5/116:00 am
BOS
-
HHH
2 stops9h 33m
Delta
Deal found 3/19$362
This American Airlines deal was found by Cheapflights users on 3/18. 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 5/2011:03 am
HHH
-
BOS
1 stop7h 00m
American Airlines
Wed 5/278:04 am
BOS
-
HHH
2 stops6h 09m
American Airlines
Deal found 3/18$397
This Delta deal was found by Cheapflights users on 3/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/104:00 pm
HHH
-
BOS
1 stop7h 25m
Delta
Sun 7/125:30 am
BOS
-
HHH
2 stops9h 48m
Delta
Deal found 3/19$401
This Delta deal was found by Cheapflights users on 3/20. 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.
Wed 7/112:00 pm
HHH
-
BOS
2 stops11h 17m
Delta
Tue 7/215:30 am
BOS
-
HHH
2 stops9h 48m
Delta
Deal found 3/20$402
This United Airlines deal was found by Cheapflights users on 3/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/93:05 pm
HHH
-
BOS
1 stop6h 54m
United Airlines
Sat 4/1110:05 am
BOS
-
HHH
1 stop5h 25m
United Airlines
Deal found 3/19$409
This United Airlines deal was found by Cheapflights users on 3/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/103:05 pm
HHH
-
BOS
2 stops8h 54m
United Airlines
Sun 4/127:00 am
BOS
-
HHH
1 stop7h 16m
United Airlines
Deal found 3/19$414

Find 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 March 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$334
(United Airlines)

One-way from

$179
(Delta)

Popular in

June

Cheapest in

April
Provider with most accurate pricing for Hilton Head Island-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Boston Logan Intl flights.
Search Deals
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. 29% potential increase in price ($128 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($22 potential savings vs. average RT price).
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 March 20, 2026.
Use the filters below to find and compare flights from Hilton Head Island to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 4/1

4:11 pm-9:54 pm

1 stop5h 43m

Boston Logan Intl

Sun 4/5

5:45 am-2:16 pm

2 stops8h 31m

$344

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 4/1

4:11 pm-11:59 pm

2 stops7h 48m

Boston Logan Intl

Tue 4/7

5:45 am-2:16 pm

2 stops8h 31m

$344

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 7/1

4:00 pm-10:27 pm

1 stop6h 27m

Boston Logan Intl

Tue 7/21

5:30 am-3:18 pm

2 stops9h 48m

$362

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 5/8

4:16 pm-10:25 pm

1 stop6h 09m

Boston Logan Intl

Mon 5/11

8:00 am-3:33 pm

1 stop7h 33m

$412

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 6/3

3:05 pm-11:59 pm

2 stops8h 54m

Boston Logan Intl

Sun 6/7

7:30 am-12:52 pm

1 stop5h 22m

$419

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sat 5/23

4:16 pm-9:15 am

1 stop16h 59m

Boston Logan Intl

Mon 5/25

6:00 am-11:37 am

1 stop5h 37m

$444
Quickest round-trip

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 4/10

3:05 pm-9:59 pm

1 stop6h 54m

Boston Logan Intl

Sat 4/11

10:05 am-3:30 pm

1 stop5h 25m

$459

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 3/31

3:00 pm-9:59 pm

1 stop6h 59m

Boston Logan Intl

Sat 4/4

6:00 am-2:16 pm

1 stop8h 16m

$539

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Sun 5/24

4:16 pm-10:25 pm

1 stop6h 09m

Boston Logan Intl

Mon 5/25

12:00 pm-11:37 am

1 stop23h 37m

$545

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 4/24

3:05 pm-9:59 pm

1 stop6h 54m

Boston Logan Intl

Wed 4/29

5:45 am-3:30 pm

2 stops9h 45m

$560

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/18

Showing 1-10 of 20 resultsSorted by cheapest first
1
2
  • 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 November is currently the most expensive (average of $93). 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.

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 March 20, 2026.
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
7.1
Good
11,480 reviews

Boarding

7.5

Crew

7.9

Comfort

7.2

Food

6.4

Overall

7.1

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,480 reviews
American Airlines
7.1
Good
11,480 reviews

Boarding

7.5

Crew

7.9

Comfort

7.2

Food

6.4

Overall

7.1

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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 5h 43m. 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 $216 on this airline. American Airlines is currently priced 29% 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 November is currently the most expensive (average of $93). 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
Medford
Cambridge
Concord
Hampton Beach
Watertown
Seekonk
Brockton
Seabrook
Cranston
Chelsea
Smithfield
Lincoln
Warwick
Peabody
Waltham
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy

Browse thousands of different options on Cheapflights for your next trip

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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 March 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$216Average$334FlexibilityNo cancel feeOn-time71%

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