$188+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Jul 19 — Jul 261
Round-trip
1 adult, Economy
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Find cheap flights from Hilton Head Island to Boston with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Hilton Head Island to Boston
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Cheapest flights from Hilton Head Island to BostonExplore 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 June 19, 2026.
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 June 19, 2026.
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Sat 7/42:56 pm
HHH
- BOS
Nonstop2h 36m
American Airlines
Fri 7/106:05 am
BOS
- HHH
1 stop5h 12m
American Airlines
Deal found 6/15![American Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 6/17. 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.
Tue 7/142:48 pm
HHH
- BOS
1 stop6h 11m
American Airlines
Tue 7/2110:13 am
BOS
- HHH
1 stop6h 12m
American Airlines
Deal found 6/17![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 6/17. 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.
Tue 7/144:14 pm
HHH
- BOS
1 stop6h 19m
Delta
Tue 7/217:00 am
BOS
- HHH
2 stops8h 29m
Delta
Deal found 6/17![Delta logo]()
$314
This American Airlines deal was found by Cheapflights users on 6/17. 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.
Wed 7/15:21 pm
HHH
- BOS
1 stop7h 19m
American Airlines
Sat 7/411:41 am
BOS
- HHH
Nonstop2h 45m
American Airlines
Deal found 6/17![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 6/16. 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 7/282:48 pm
HHH
- BOS
1 stop5h 22m
American Airlines
Thu 8/65:27 am
BOS
- HHH
1 stop5h 42m
American Airlines
Deal found 6/16![American Airlines logo]()
$347
This American Airlines deal was found by Cheapflights users on 6/17. 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.
Mon 7/202:48 pm
HHH
- BOS
1 stop5h 22m
American Airlines
Tue 8/257:26 am
BOS
- HHH
1 stop7h 31m
American Airlines
Deal found 6/17![American Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Fri 7/1011:47 am
HHH
- BOS
1 stop6h 17m
American Airlines
Sun 7/126:05 am
BOS
- HHH
1 stop5h 12m
American Airlines
Deal found 6/15![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:15 pm
HHH
- BOS
2 stops10h 32m
Delta
Sat 9/126:05 am
BOS
- HHH
2 stops9h 22m
Delta
Deal found 6/18![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3112:11 pm
HHH
- BOS
2 stops11h 20m
Delta
Fri 8/76:05 am
BOS
- HHH
2 stops9h 27m
Delta
Deal found 6/16![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 6/17. 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.
Sat 7/252:45 pm
HHH
- BOS
Nonstop2h 36m
American Airlines
Sat 8/111:30 am
BOS
- HHH
Nonstop2h 45m
American Airlines
Deal found 6/17![American Airlines logo]()
$367
Best flights from Hilton Head Island to BostonDiscover carefully curated flight deals from Hilton Head Island to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 19, 2026.
Discover carefully curated flight deals from Hilton Head Island to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 19, 2026.
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/174:14 pm
HHH
- BOS
1 stop5h 25m
Delta
Thu 7/236:00 am
BOS
- HHH
1 stop5h 24m
Delta
Deal found 6/18![Delta logo]()
$309
This United Airlines deal was found by Cheapflights users on 6/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:48 pm
HHH
- BOS
1 stop8h 46m
United Airlines
Sat 8/297:05 am
BOS
- HHH
1 stop6h 58m
United Airlines
Deal found 6/14![United Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 6/14. 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.
Wed 7/2912:11 pm
HHH
- BOS
1 stop7h 19m
Delta
Wed 8/56:00 am
BOS
- HHH
2 stops9h 32m
Delta
Deal found 6/14![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 6/14. 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.
Tue 7/1412:11 pm
HHH
- BOS
2 stops7h 49m
Delta
Tue 7/216:00 am
BOS
- HHH
1 stop5h 24m
Delta
Deal found 6/14![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3112:11 pm
HHH
- BOS
1 stop7h 19m
Delta
Fri 8/76:05 am
BOS
- HHH
2 stops9h 27m
Delta
Deal found 6/16![Delta logo]()
$374
Last-minute flights from Hilton Head Island to BostonDiscover last-minute flight deals from Hilton Head Island to Boston. Data last updated June 19, 2026 and is based on user searches.
Discover last-minute flight deals from Hilton Head Island to Boston. Data last updated June 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/17. 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.
Wed 7/15:21 pm
HHH
- BOS
1 stop7h 19m
American Airlines
Sat 7/411:41 am
BOS
- HHH
Nonstop2h 45m
American Airlines
Deal found 6/17![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Sat 7/42:56 pm
HHH
- BOS
Nonstop2h 36m
American Airlines
Fri 7/106:05 am
BOS
- HHH
1 stop5h 12m
American Airlines
Deal found 6/15![American Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Fri 7/1011:47 am
HHH
- BOS
1 stop6h 17m
American Airlines
Sun 7/126:05 am
BOS
- HHH
1 stop5h 12m
American Airlines
Deal found 6/15![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 6/17. 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.
Tue 7/142:48 pm
HHH
- BOS
1 stop6h 11m
American Airlines
Tue 7/2110:13 am
BOS
- HHH
1 stop6h 12m
American Airlines
Deal found 6/17![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 6/17. 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.
Tue 7/144:14 pm
HHH
- BOS
1 stop6h 19m
Delta
Tue 7/217:00 am
BOS
- HHH
2 stops8h 29m
Delta
Deal found 6/17![Delta logo]()
$314
This American Airlines deal was found by Cheapflights users on 6/17. 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.
Mon 7/202:48 pm
HHH
- BOS
1 stop5h 22m
American Airlines
Tue 8/257:26 am
BOS
- HHH
1 stop7h 31m
American Airlines
Deal found 6/17![American Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 6/17. 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.
Sat 7/252:45 pm
HHH
- BOS
Nonstop2h 36m
American Airlines
Sat 8/111:30 am
BOS
- HHH
Nonstop2h 45m
American Airlines
Deal found 6/17![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 6/16. 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 7/282:48 pm
HHH
- BOS
1 stop5h 22m
American Airlines
Thu 8/65:27 am
BOS
- HHH
1 stop5h 42m
American Airlines
Deal found 6/16![American Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3112:11 pm
HHH
- BOS
2 stops11h 20m
Delta
Fri 8/76:05 am
BOS
- HHH
2 stops9h 27m
Delta
Deal found 6/16![Delta logo]()
$364
One-way flights from Hilton Head Island to BostonSearch for one-way flight options from Hilton Head Island to Boston. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
Search for one-way flight options from Hilton Head Island to Boston. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
This American Airlines deal was found by Cheapflights users on 6/18. 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 8/510:57 am
HHH
- BOS
1 stop13h 02m
American Airlines
Deal found 6/18![American Airlines logo]()
$188
This Delta deal was found by Cheapflights users on 6/15. 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.
Sat 9/124:10 pm
HHH
- BOS
1 stop25h 20m
Delta
Deal found 6/15![Delta logo]()
$194
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:15 pm
HHH
- BOS
2 stops22h 00m
Delta
Deal found 6/16![Delta logo]()
$199
This Delta deal was found by Cheapflights users on 6/15. 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.
Wed 9/912:15 pm
HHH
- BOS
2 stops11h 02m
Delta
Deal found 6/15![Delta logo]()
$200
This Delta deal was found by Cheapflights users on 6/15. 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.
Thu 9/104:10 pm
HHH
- BOS
1 stop25h 21m
Delta
Deal found 6/15![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:15 pm
HHH
- BOS
2 stops19h 10m
Delta
Deal found 6/18![Delta logo]()
$212
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/104:18 pm
HHH
- BOS
2 stops15h 27m
Delta
Deal found 6/16![Delta logo]()
$213
This Delta deal was found by Cheapflights users on 6/17. 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.
Tue 7/144:14 pm
HHH
- BOS
1 stop15h 01m
Delta
Deal found 6/17![Delta logo]()
$219
This Delta deal was found by Cheapflights users on 6/15. 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.
Wed 8/1212:15 pm
HHH
- BOS
2 stops20h 06m
Delta
Deal found 6/15![Delta logo]()
$220
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 June 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $300 (American Airlines) |
One-way from | $188 (American Airlines) |
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 June 19, 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
Cheapest round-trip
Quickest round-trip
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Fri 7/17
4:14 pm-9:39 pm
1 stop5h 25m
Boston Logan Intl
Thu 7/23
6:00 am-11:24 am
1 stop5h 24m
$309
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Wed 7/29
12:11 pm-7:30 pm
1 stop7h 19m
Boston Logan Intl
Wed 8/5
6:00 am-3:32 pm
2 stops9h 32m
$314
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Tue 7/14
12:11 pm-8:00 pm
2 stops7h 49m
Boston Logan Intl
Tue 7/21
6:00 am-11:24 am
1 stop5h 24m
$314
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Fri 7/31
12:11 pm-7:30 pm
1 stop7h 19m
Boston Logan Intl
Fri 8/7
6:05 am-3:32 pm
2 stops9h 27m
$374
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Wed 8/26
2:48 pm-11:34 pm
1 stop8h 46m
Boston Logan Intl
Sat 8/29
7:05 am-2:03 pm
1 stop6h 58m
$389
Cheapest one-way
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Sat 9/12
4:10 pm-5:30 pm
1 stop25h 20m
$194
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Tue 9/15
4:10 pm-7:15 am
1 stop15h 05m
$194
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Mon 9/14
4:10 pm-10:27 am
1 stop18h 17m
$209
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Thu 9/10
4:10 pm-5:31 pm
1 stop25h 21m
$209
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Tue 8/11
12:15 pm-8:23 am
2 stops20h 08m
$220
Showing 1-10 of 12 resultsSorted by cheapest first
- 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.
HHH-BOS
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
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 June 19, 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.
Crew
7.9
Entertainment
6.8
Food
6.4
Boarding
7.5
Overall
7.1
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Crew
7.9
Entertainment
6.8
Food
6.4
Boarding
7.5
Overall
7.1
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
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.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Cambridge
Concord
Brockton
Watertown
Hampton Beach
Seekonk
Cranston
Warwick
Peabody
Auburn
York Beach
Chelsea
Londonderry
Dedham
Swansea
Old Orchard Beach
Lowell
Smithfield
Braintree
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Hilton Head Island and Boston flights
Browse other Hilton Head Island and Boston flight options. Last updated on June 19, 2026.
Other flights from Hilton Head Island
Browse through other flights departing from Hilton Head Island. Flights are based on user searches made on Cheapflights and were last updated on June 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 June 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$216 | Average$423 | FlexibilityNo cancel fee | On-time71% |