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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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Jun 15 — Jun 221
Mon 6/15
Mon 6/22
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 May 16, 2026.

This American Airlines deal was found by Cheapflights users on 5/13. 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 5/2312:16 pm
HHH
-
BOS
Nonstop2h 38m
American Airlines
Sat 6/612:10 pm
BOS
-
HHH
Nonstop2h 59m
American Airlines
Deal found 5/13$251
This American Airlines deal was found by Cheapflights users on 5/12. 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 6/22:43 pm
HHH
-
BOS
1 stop5h 25m
American Airlines
Sat 6/612:10 pm
BOS
-
HHH
Nonstop2h 59m
American Airlines
Deal found 5/12$261
This United Airlines deal was found by Cheapflights users on 5/15. 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.
Tue 6/21:45 pm
HHH
-
BOS
1 stop5h 43m
United Airlines
Tue 6/96:00 am
BOS
-
HHH
1 stop6h 59m
United Airlines
Deal found 5/15$271
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Fri 5/292:43 pm
HHH
-
BOS
1 stop6h 17m
American Airlines
Tue 6/29:18 am
BOS
-
HHH
2 stops7h 14m
American Airlines
Deal found 5/14$276
This American Airlines deal was found by Cheapflights users on 5/14. 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 6/32:43 pm
HHH
-
BOS
1 stop6h 17m
American Airlines
Sun 6/76:00 am
BOS
-
HHH
1 stop5h 10m
American Airlines
Deal found 5/14$290
This American Airlines deal was found by Cheapflights users on 5/14. 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.
Thu 5/215:21 pm
HHH
-
BOS
1 stop7h 19m
American Airlines
Thu 5/286:00 am
BOS
-
HHH
1 stop4h 27m
American Airlines
Deal found 5/14$291

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 May 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$251
(American Airlines)

One-way from

$126
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$519
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. 35% potential increase in price ($196 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 16, 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
Quickest round-trip

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 6/2

2:43 pm-8:08 pm

1 stop5h 25m

Boston Logan Intl

Sat 6/6

12:10 pm-3:09 pm

Nonstop2h 59m

$261

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 6/2

1:45 pm-11:59 pm

2 stops10h 14m

Boston Logan Intl

Tue 6/9

6:00 am-2:21 pm

1 stop8h 21m

$276

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 6/3

2:43 pm-10:26 pm

2 stops7h 43m

Boston Logan Intl

Sun 6/7

7:00 am-12:26 pm

1 stop5h 26m

$324

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 7/10

2:48 pm-8:10 pm

1 stop5h 22m

Boston Logan Intl

Sun 7/12

6:04 am-12:20 pm

1 stop6h 16m

$384

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 6/5

1:45 pm-7:28 pm

1 stop5h 43m

Boston Logan Intl

Tue 6/9

7:19 am-2:21 pm

1 stop7h 02m

$485

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 7/10

12:11 pm-10:47 pm

2 stops10h 36m

Boston Logan Intl

Sun 7/12

5:30 am-3:29 pm

2 stops9h 59m

$525

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 10/16

1:45 pm-7:31 pm

1 stop5h 46m

Boston Logan Intl

Sun 10/18

6:00 am-12:52 pm

1 stop6h 52m

$531
Cheapest one-way

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Wed 8/12

4:12 pm-9:47 pm

1 stop5h 35m

$136

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Fri 8/21

2:48 pm-12:34 am

1 stop9h 46m

$136

Hilton Head IslandBoston

HHH - BOS

HHHBOS

Hilton Head Island

Tue 8/11

4:12 pm-9:47 pm

1 stop5h 35m

$136

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

Showing 1-10 of 18 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

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 May 16, 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
11,662 reviews

Food

6.4

Crew

7.9

Entertainment

6.9

Comfort

7.2

Overall

7.1

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!
American Airlines
7.1
Good
11,662 reviews
American Airlines
7.1
Good
11,662 reviews

Food

6.4

Crew

7.9

Entertainment

6.9

Comfort

7.2

Overall

7.1

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Apr 2026

DFW - BDL

They keep changing the gate, delaying the hours and then finally canceled it. No accomodation, no food, nothing!

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 25m. 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 $250 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.

See more FAQs

Traveling to a place near Boston?

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

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 May 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$250Average$422FlexibilityNo cancel feeOn-time71%

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