$180+ 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Nov 30 — Dec 71
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 October 31, 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 October 31, 2026.
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/45:54 pm -
1 stop5h 08m
Mon 12/77:11 am -
1 stop4h 52m
Deal found 10/29![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/104:17 pm -
1 stop5h 33m
Sat 11/149:26 am -
1 stop6h 21m
Deal found 10/26![American Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 10/26. 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 11/312:23 pm -
1 stop6h 44m
Sat 11/78:00 am -
1 stop7h 30m
Deal found 10/26![Delta logo]()
$437
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/412:25 pm -
1 stop6h 45m
Tue 11/108:16 am -
2 stops7h 28m
Deal found 10/29![American Airlines logo]()
$446
This Delta deal was found by Cheapflights users on 10/27. 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 10/274:13 pm -
1 stop7h 07m
Sun 11/17:00 am -
1 stop4h 43m
Deal found 10/27![Delta logo]()
$458
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 October 31, 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 October 31, 2026.
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/104:17 pm -
1 stop5h 33m
Sat 11/149:26 am -
1 stop6h 21m
Deal found 10/26![American Airlines logo]()
$389
This United Airlines deal was found by Cheapflights users on 10/30. 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 4/283:05 pm -
1 stop8h 11m
Sat 5/17:10 am -
1 stop7h 06m
Deal found 10/30![United Airlines logo]()
$459
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/1112:25 pm -
2 stops9h 21m
Sun 11/1510:12 am -
1 stop6h 58m
Deal found 10/27![American Airlines logo]()
$422
Last-minute flights from Hilton Head Island to BostonDiscover last-minute flight deals from Hilton Head Island to Boston. Data last updated October 31, 2026 and is based on user searches.
Discover last-minute flight deals from Hilton Head Island to Boston. Data last updated October 31, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/29. 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 10/296:08 pm -
1 stop4h 51m
Sun 11/17:05 am -
1 stop7h 16m
Deal found 10/29![American Airlines logo]()
$479
This Delta deal was found by Cheapflights users on 10/26. 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 11/312:23 pm -
1 stop6h 44m
Sat 11/78:00 am -
1 stop7h 30m
Deal found 10/26![Delta logo]()
$437
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/412:25 pm -
1 stop6h 45m
Tue 11/108:16 am -
2 stops7h 28m
Deal found 10/29![American Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/104:17 pm -
1 stop5h 33m
Sat 11/149:26 am -
1 stop6h 21m
Deal found 10/26![American Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/1112:25 pm -
2 stops11h 26m
Sun 11/156:50 am -
2 stops7h 31m
Deal found 10/27![American Airlines logo]()
$568
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/122:51 pm -
1 stop5h 09m
Mon 11/167:29 pm -
2 stops16h 24m
Deal found 10/28![American Airlines logo]()
$492
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/1412:29 pm -
1 stop6h 41m
Wed 11/1811:18 am -
1 stop4h 26m
Deal found 10/30![American Airlines logo]()
$586
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 October 31, 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 October 31, 2026.
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/232:49 pm -
1 stop6h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![American Airlines logo]()
$180
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/283:02 pm -
1 stop4h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![American Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/104:17 pm -
1 stop5h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 10/27. 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 12/3011:08 am -
2 stops11h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$418
This Delta deal was found by Cheapflights users on 10/26. 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 11/64:13 pm -
1 stop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Delta logo]()
$444
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/62:51 pm -
2 stops8h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 10/29. 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 4/274:00 pm -
1 stop6h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$494
This American Airlines deal was found by Cheapflights users on 10/30. 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 10/30![American Airlines logo]()
$508
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 October 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $359 (American Airlines) |
One-way from | $180 (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 7,457,451 searches. Data last updated October 31, 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
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Mon 11/23
2:49 pm-8:56 pm
1 stop6h 07m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$180
Quickest round-trip
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Mon 12/28
3:02 pm-7:15 pm
1 stop4h 13m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$264
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Tue 11/10
4:17 pm-9:50 pm
1 stop5h 33m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$389
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Tue 11/10
4:17 pm-9:50 pm
1 stop5h 33m
Boston Logan Intl
Sat 11/14
9:26 am-3:47 pm
1 stop6h 21m
$389
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Wed 12/30
11:08 am-10:42 pm
2 stops11h 34m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$418
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Wed 11/11
12:25 pm-9:46 pm
2 stops9h 21m
Boston Logan Intl
Sun 11/15
10:12 am-5:10 pm
1 stop6h 58m
$422
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Fri 11/6
4:13 pm-10:24 pm
1 stop6h 11m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$444
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Fri 11/6
2:51 pm-11:13 pm
2 stops8h 22m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$449
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Wed 4/28
3:05 pm-11:16 pm
1 stop8h 11m
Boston Logan Intl
Sat 5/1
7:10 am-2:16 pm
1 stop7h 06m
$459
Hilton Head IslandBoston
HHH Hilton Head Island - BOS Boston Logan Intl
HHHBOS
Hilton Head Island
Tue 4/27
4:00 pm-10:21 pm
1 stop6h 21m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$494
Showing 1-10 of 11 resultsSorted by cheapest first
Compare providers for flights from Hilton Head Island to Boston
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Hilton Head Island to Boston in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- 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 October 31, 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.
Entertainment
6.8
Crew
7.9
Overall
7.0
Boarding
7.4
Food
6.4
Comfort
7.2
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
Entertainment
6.8
Crew
7.9
Overall
7.0
Boarding
7.4
Food
6.4
Comfort
7.2
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
Warwick
Pawtucket
Peabody
Fitchburg
Londonderry
York Beach
Revere
North Falmouth
Chelsea
Swansea
Braintree
Auburn
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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Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 31, 2026.
Complete your trip
Complete your trip to Boston by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Hilton Head Island to Boston by cabin class
Find flights from Hilton Head Island to Boston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hilton Head Island and Boston flights
Browse other Hilton Head Island and Boston flight options. Last updated on October 31, 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 October 31, 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 October 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$251 | Average$427 | FlexibilityNo cancel fee | On-time71% |