$169+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Aug 31 — Sep 71
Round-trip
1 adult, Economy
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Find cheap flights from Hilton Head Island to Boston with Cheapflights
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Best
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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 August 1, 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 August 1, 2026.
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:15 pm
HHH
- BOS
1 stop5h 55m
Delta
Tue 9/88:00 am
BOS
- HHH
1 stop7h 27m
Delta
Deal found 7/28![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 7/27. 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 8/113:27 pm
HHH
- BOS
1 stop6h 46m
American Airlines
Sat 8/1510:09 am
BOS
- HHH
Nonstop2h 51m
American Airlines
Deal found 7/27![American Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 9/102:48 pm
HHH
- BOS
1 stop7h 11m
United Airlines
Thu 9/176:00 am
BOS
- HHH
1 stop6h 59m
United Airlines
Deal found 7/30![United Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Wed 8/1911:40 am
HHH
- BOS
1 stop7h 34m
American Airlines
Sat 8/225:27 am
BOS
- HHH
1 stop5h 42m
American Airlines
Deal found 7/30![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sun 9/136:29 pm
HHH
- BOS
1 stop4h 31m
American Airlines
Sun 9/206:00 am
BOS
- HHH
1 stop5h 18m
American Airlines
Deal found 7/30![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 7/30. 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 8/192:58 pm
HHH
- BOS
2 stops9h 01m
United Airlines
Sat 8/227:05 am
BOS
- HHH
1 stop6h 58m
United Airlines
Deal found 7/30![United Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 8/113:27 pm
HHH
- BOS
1 stop4h 39m
American Airlines
Tue 8/2511:35 am
BOS
- HHH
1 stop5h 03m
American Airlines
Deal found 7/30![American Airlines logo]()
$358
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 August 1, 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 August 1, 2026.
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:15 pm
HHH
- BOS
1 stop5h 55m
Delta
Mon 9/77:00 am
BOS
- HHH
1 stop4h 34m
Delta
Deal found 7/28![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 7/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:58 pm
HHH
- BOS
2 stops9h 01m
United Airlines
Sat 8/225:45 am
BOS
- HHH
2 stops8h 18m
United Airlines
Deal found 7/26![United Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:18 pm
HHH
- BOS
1 stop5h 29m
Delta
Sun 9/67:00 am
BOS
- HHH
1 stop4h 34m
Delta
Deal found 7/28![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:15 pm
HHH
- BOS
2 stops10h 21m
Delta
Tue 9/88:00 am
BOS
- HHH
1 stop7h 27m
Delta
Deal found 7/28![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:15 pm
HHH
- BOS
2 stops10h 21m
Delta
Mon 9/77:00 am
BOS
- HHH
1 stop4h 34m
Delta
Deal found 7/28![Delta logo]()
$324
This United Airlines deal was found by Cheapflights users on 7/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:58 pm
HHH
- BOS
1 stop7h 01m
United Airlines
Mon 8/315:45 am
BOS
- HHH
2 stops8h 18m
United Airlines
Deal found 7/26![United Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/22:58 pm
HHH
- BOS
1 stop8h 36m
United Airlines
Sun 9/65:45 am
BOS
- HHH
2 stops8h 18m
United Airlines
Deal found 7/30![United Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 8/142:58 pm
HHH
- BOS
1 stop7h 01m
United Airlines
Tue 8/187:30 am
BOS
- HHH
1 stop5h 35m
United Airlines
Deal found 7/30![United Airlines logo]()
$437
Last-minute flights from Hilton Head Island to BostonDiscover last-minute flight deals from Hilton Head Island to Boston. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from Hilton Head Island to Boston. Data last updated August 1, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 7/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/73:05 pm
HHH
- BOS
1 stop8h 16m
United Airlines
Mon 8/107:19 am
BOS
- HHH
1 stop7h 02m
United Airlines
Deal found 7/26![United Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 7/26. 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 8/711:40 am
HHH
- BOS
1 stop7h 34m
American Airlines
Mon 8/106:00 am
BOS
- HHH
1 stop4h 27m
American Airlines
Deal found 7/26![American Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Sun 8/95:46 pm
HHH
- BOS
1 stop5h 23m
American Airlines
Sun 8/165:32 am
BOS
- HHH
1 stop5h 37m
American Airlines
Deal found 7/26![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Mon 8/1011:40 am
HHH
- BOS
1 stop5h 06m
American Airlines
Thu 8/136:00 am
BOS
- HHH
1 stop4h 27m
American Airlines
Deal found 7/28![American Airlines logo]()
$632
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 August 1, 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 August 1, 2026.
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/284:17 pm
HHH
- BOS
1 stop6h 09m
Delta
Deal found 7/28![Delta logo]()
$169
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:23 pm
HHH
- BOS
2 stops7h 06m
Delta
Deal found 7/28![Delta logo]()
$174
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 8/284:18 pm
HHH
- BOS
1 stop5h 29m
Delta
Deal found 7/29![Delta logo]()
$179
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 8/2612:15 pm
HHH
- BOS
2 stops10h 32m
Delta
Deal found 7/29![Delta logo]()
$184
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Thu 10/15:15 pm
HHH
- BOS
1 stop5h 09m
American Airlines
Deal found 7/27![American Airlines logo]()
$200
This Delta deal was found by Cheapflights users on 7/27. 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.
Mon 8/2412:15 pm
HHH
- BOS
2 stops10h 32m
Delta
Deal found 7/27![Delta logo]()
$205
This American Airlines deal was found by Cheapflights users on 7/27. 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 8/2511:40 am
HHH
- BOS
1 stop7h 34m
American Airlines
Deal found 7/27![American Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:15 pm
HHH
- BOS
1 stop7h 20m
Delta
Deal found 7/28![Delta logo]()
$210
This Delta deal was found by Cheapflights users on 7/29. 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 8/2512:15 pm
HHH
- BOS
2 stops10h 32m
Delta
Deal found 7/29![Delta logo]()
$215
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:50 pm
HHH
- BOS
2 stops10h 09m
United Airlines
Deal found 7/29![United Airlines logo]()
$216
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/302:58 pm
HHH
- BOS
1 stop8h 36m
United Airlines
Deal found 7/29![United Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:58 pm
HHH
- BOS
2 stops9h 01m
United Airlines
Deal found 7/29![United Airlines logo]()
$224
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 August 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (American Airlines) |
One-way from | $169 (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 2,558,603 searches. Data last updated August 1, 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 - BOS
HHHBOS
Hilton Head Island
Wed 9/2
12:15 pm-6:10 pm
1 stop5h 55m
Boston Logan Intl
Mon 9/7
7:00 am-11:34 am
1 stop4h 34m
$319
Quickest round-trip
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Wed 9/2
4:18 pm-9:47 pm
1 stop5h 29m
Boston Logan Intl
Sun 9/6
7:00 am-11:34 am
1 stop4h 34m
$319
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Tue 9/1
12:15 pm-10:36 pm
2 stops10h 21m
Boston Logan Intl
Tue 9/8
8:00 am-3:27 pm
1 stop7h 27m
$324
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Tue 9/1
12:15 pm-10:36 pm
2 stops10h 21m
Boston Logan Intl
Mon 9/7
7:00 am-11:34 am
1 stop4h 34m
$324
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Wed 8/19
2:58 pm-11:59 pm
2 stops9h 01m
Boston Logan Intl
Sat 8/22
5:45 am-2:03 pm
2 stops8h 18m
$351
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Thu 8/27
2:58 pm-9:59 pm
1 stop7h 01m
Boston Logan Intl
Mon 8/31
5:45 am-2:03 pm
2 stops8h 18m
$404
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Wed 9/2
2:58 pm-11:34 pm
1 stop8h 36m
Boston Logan Intl
Sun 9/6
5:45 am-2:03 pm
2 stops8h 18m
$404
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Fri 8/14
2:58 pm-9:59 pm
1 stop7h 01m
Boston Logan Intl
Tue 8/18
7:30 am-1:05 pm
1 stop5h 35m
$437
Cheapest one-way
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Wed 10/28
12:23 pm-5:57 pm
1 stop5h 34m
$169
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Mon 9/28
4:17 pm-10:26 pm
1 stop6h 09m
$169
Showing 1-10 of 16 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 August 1, 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.
Comfort
7.2
Entertainment
6.8
Boarding
7.5
Crew
7.9
Food
6.4
Overall
7.1
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
Comfort
7.2
Entertainment
6.8
Boarding
7.5
Crew
7.9
Food
6.4
Overall
7.1
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
Cambridge
Concord
Randolph
Brockton
Seekonk
Hampton Beach
Cranston
Warwick
Peabody
Dedham
Auburn
York Beach
Chelsea
Londonderry
Swansea
Fitchburg
North Falmouth
Braintree
Revere
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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 August 1, 2026.
Complete your trip
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Hilton Head Island and Boston flights
Browse other Hilton Head Island and Boston flight options. Last updated on August 1, 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 August 1, 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 August 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$423 | FlexibilityNo cancel fee | On-time71% |