$284+ Cheap flights from Hilton Head Island to Boston (HHH - BOS)
This is the cheapest round-trip 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 17 — Oct 241
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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Best
Last-minute
One-way
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 September 17, 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 September 17, 2026.
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.
Wed 10/1410:55 am -
1 stop5h 59m
Wed 10/2110:15 am -
1 stop7h 23m
Deal found 9/14![American Airlines logo]()
$328
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.
Thu 11/54:13 pm -
1 stop6h 11m
Sun 11/87:00 am -
1 stop4h 43m
Deal found 9/15![Delta logo]()
$339
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 10/2012:29 pm -
2 stops8h 20m
Mon 10/266:00 am -
1 stop4h 25m
Deal found 9/15![American Airlines logo]()
$350
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.
Tue 9/2912:17 pm -
1 stop6h 48m
Sat 10/37:55 am -
1 stop7h 32m
Deal found 9/14![Delta logo]()
$369
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.
Thu 11/511:04 am -
1 stop4h 43m
Sun 11/86:00 am -
2 stops8h 21m
Deal found 9/16![American Airlines logo]()
$378
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 September 17, 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 September 17, 2026.
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.
Thu 11/54:13 pm -
1 stop6h 11m
Sun 11/87:00 am -
1 stop4h 43m
Deal found 9/15![Delta logo]()
$339
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.
Thu 11/55:54 pm -
1 stop5h 13m
Sun 11/810:12 am -
1 stop6h 58m
Deal found 9/16![American Airlines logo]()
$339
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 9/301:20 pm -
1 stop6h 05m
Sun 10/47:38 am -
1 stop4h 57m
Deal found 9/15![United Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 10/142:56 pm -
2 stops8h 29m
Sun 10/186:00 am -
1 stop4h 25m
Deal found 9/13![American Airlines logo]()
$346
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.
Tue 9/2912:17 pm -
1 stop6h 48m
Sat 10/37:55 am -
1 stop7h 32m
Deal found 9/14![Delta logo]()
$369
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:17 pm -
2 stops10h 09m
Mon 10/58:00 am -
1 stop7h 27m
Deal found 9/16![Delta logo]()
$374
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:20 pm -
1 stop6h 05m
Sat 10/247:55 am -
1 stop6h 15m
Deal found 9/16![United Airlines logo]()
$419
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:17 pm -
2 stops10h 09m
Mon 10/56:05 am -
2 stops9h 22m
Deal found 9/16![Delta logo]()
$379
Last-minute flights from Hilton Head Island to BostonDiscover last-minute flight deals from Hilton Head Island to Boston. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Hilton Head Island to Boston. Data last updated September 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/17. 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 9/1912:50 pm -
1 stop5h 50m
Wed 9/237:19 am -
1 stop6h 26m
Deal found 9/17![American Airlines logo]()
$404
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.
Tue 9/2912:17 pm -
1 stop6h 48m
Sat 10/37:55 am -
1 stop7h 32m
Deal found 9/14![Delta logo]()
$369
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.
Wed 10/1410:55 am -
1 stop5h 59m
Wed 10/2110:15 am -
1 stop7h 23m
Deal found 9/14![American Airlines logo]()
$328
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 10/2012:29 pm -
2 stops8h 20m
Mon 10/266:00 am -
1 stop4h 25m
Deal found 9/15![American Airlines logo]()
$350
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 September 17, 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 September 17, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/144:13 pm -
1 stop7h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 9/17. 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 10/1312:23 pm -
2 stops9h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$289
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.
Fri 12/1811:07 am -
1 stop4h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![American Airlines logo]()
$304
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/106:13 pm -
1 stop4h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![American Airlines logo]()
$310
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.
Fri 3/124:11 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$314
This United Airlines deal was found by Cheapflights users on 9/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/102:51 pm -
2 stops9h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![United Airlines logo]()
$329
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.
Sun 3/146:22 pm -
1 stop4h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 9/12. 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.
Sat 3/132:58 pm -
1 stop6h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![American Airlines logo]()
$340
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.
Wed 12/912:25 pm -
2 stops10h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![American Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 9/17. 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.
Sat 10/174:13 pm -
1 stop16h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$349
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.
Mon 11/1612:25 pm -
2 stops10h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$355
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $328 (American Airlines) |
One-way from | $284 (Delta) |
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 7,457,451 searches. Data last updated September 17, 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 Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Thu 10/15
4:13 pm-9:29 pm
1 stop5h 16m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Tue 3/16
2:58 pm-9:49 pm
1 stop6h 51m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Fri 10/9
4:13 pm-10:24 pm
1 stop6h 11m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Thu 12/17
3:02 pm-8:54 pm
1 stop5h 52m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Tue 12/15
4:17 pm-9:50 pm
1 stop5h 33m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Fri 10/16
4:13 pm-11:20 pm
1 stop7h 07m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Wed 10/14
4:13 pm-11:20 pm
1 stop7h 07m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Fri 10/30
12:23 pm-10:55 pm
2 stops10h 32m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$289
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Tue 10/13
12:23 pm-10:24 pm
2 stops10h 01m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$289
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Thu 11/5
4:13 pm-10:24 pm
1 stop6h 11m
Boston Logan Intl
Sun 11/8
7:00 am-11:43 am
1 stop4h 43m
$339
Showing 1-10 of 17 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.
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 17, 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.
Food
6.4
Entertainment
6.8
Overall
7.1
Comfort
7.2
Boarding
7.4
Crew
7.9
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
Food
6.4
Entertainment
6.8
Overall
7.1
Comfort
7.2
Boarding
7.4
Crew
7.9
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
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
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Revere
Warwick
Pawtucket
Peabody
Auburn
Londonderry
York Beach
Fitchburg
North Falmouth
Swansea
Chelsea
Braintree
Sandwich
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Complete your trip
Complete your trip to Boston by adding a car rental and/or hotel reservation to your travel itinerary.
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Hilton Head Island and Boston flights
Browse other Hilton Head Island and Boston flight options. Last updated on September 17, 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 September 17, 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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$251 | Average$427 | FlexibilityNo cancel fee | On-time71% |