$129+ 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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — BOS
Jun 3 — Jun 101
Round-trip
1 adult, Economy
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Find cheap flights from Hilton Head Island to Boston with Cheapflights
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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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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 May 4, 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 May 4, 2026.
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:16 pm
HHH
- BOS
Nonstop2h 38m
American Airlines
Sat 5/308:47 am
BOS
- HHH
Nonstop2h 59m
American Airlines
Deal found 5/3![American Airlines logo]()
$251
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/245:21 pm
HHH
- BOS
1 stop7h 19m
American Airlines
Thu 7/26:04 am
BOS
- HHH
1 stop5h 06m
American Airlines
Deal found 4/30![American Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:21 pm
HHH
- BOS
1 stop7h 19m
American Airlines
Sat 5/308:47 am
BOS
- HHH
Nonstop2h 59m
American Airlines
Deal found 5/1![American Airlines logo]()
$261
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:16 pm
HHH
- BOS
Nonstop2h 38m
American Airlines
Sat 6/612:10 pm
BOS
- HHH
Nonstop2h 59m
American Airlines
Deal found 5/4![American Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 5/2. 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 5/54:00 pm
HHH
- BOS
1 stop6h 26m
Delta
Sat 5/98:00 am
BOS
- HHH
1 stop7h 33m
Delta
Deal found 5/2![Delta logo]()
$271
This Delta deal was found by Cheapflights users on 5/2. 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 5/512:08 pm
HHH
- BOS
2 stops8h 17m
Delta
Fri 5/87:00 am
BOS
- HHH
2 stops8h 33m
Delta
Deal found 5/2![Delta logo]()
$282
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:43 pm
HHH
- BOS
1 stop5h 25m
American Airlines
Sun 6/76:00 am
BOS
- HHH
1 stop5h 10m
American Airlines
Deal found 5/4![American Airlines logo]()
$290
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 May 4, 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 May 4, 2026.
This Delta deal was found by Cheapflights users on 4/29. 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 6/244:15 pm
HHH
- BOS
1 stop7h 12m
Delta
Thu 7/26:00 am
BOS
- HHH
1 stop5h 31m
Delta
Deal found 4/29![Delta logo]()
$237
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:40 am
HHH
- BOS
1 stop6h 22m
American Airlines
Sun 6/75:31 am
BOS
- HHH
2 stops6h 55m
American Airlines
Deal found 5/2![American Airlines logo]()
$295
This United Airlines deal was found by Cheapflights users on 5/3. 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 5/231:45 pm
HHH
- BOS
1 stop5h 43m
United Airlines
Sat 5/305:45 am
BOS
- HHH
2 stops7h 07m
United Airlines
Deal found 5/3![United Airlines logo]()
$476
This Delta deal was found by Cheapflights users on 4/29. 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 6/244:15 pm
HHH
- BOS
1 stop7h 12m
Delta
Tue 6/308:05 am
BOS
- HHH
1 stop7h 27m
Delta
Deal found 4/29![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/184:15 pm
HHH
- BOS
1 stop7h 12m
Delta
Mon 6/2210:00 pm
BOS
- HHH
1 stop13h 31m
Delta
Deal found 4/30![Delta logo]()
$285
This American Airlines deal was found by Cheapflights users on 4/29. 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 7/1012:50 pm
HHH
- BOS
1 stop5h 14m
American Airlines
Sun 7/126:04 am
BOS
- HHH
1 stop6h 16m
American Airlines
Deal found 4/29![American Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:18 pm
HHH
- BOS
2 stops10h 33m
Delta
Thu 6/46:00 am
BOS
- HHH
2 stops9h 33m
Delta
Deal found 4/30![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 6/254:15 pm
HHH
- BOS
1 stop16h 06m
Delta
Thu 7/26:00 am
BOS
- HHH
1 stop5h 31m
Delta
Deal found 4/29![Delta logo]()
$330
This United Airlines deal was found by Cheapflights users on 4/30. 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 9/21:45 pm
HHH
- BOS
2 stops10h 09m
United Airlines
Sat 9/55:59 pm
BOS
- HHH
1 stop18h 53m
United Airlines
Deal found 4/30![United Airlines logo]()
$526
This Delta deal was found by Cheapflights users on 5/1. 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 5/154:16 pm
HHH
- BOS
1 stop6h 09m
Delta
Tue 5/199:10 am
BOS
- HHH
1 stop6h 23m
Delta
Deal found 5/1![Delta logo]()
$385
This Delta deal was found by Cheapflights users on 5/1. 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 5/144:16 pm
HHH
- BOS
1 stop14h 59m
Delta
Fri 5/229:00 pm
BOS
- HHH
1 stop14h 37m
Delta
Deal found 5/1![Delta logo]()
$538
Last-minute flights from Hilton Head Island to BostonDiscover last-minute flight deals from Hilton Head Island to Boston. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from Hilton Head Island to Boston. Data last updated May 4, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/1. 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 5/114:16 pm
HHH
- BOS
1 stop6h 09m
Delta
Tue 5/198:00 am
BOS
- HHH
1 stop7h 33m
Delta
Deal found 5/1![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/113:08 pm
HHH
- BOS
1 stop8h 27m
United Airlines
Sun 5/178:30 am
BOS
- HHH
1 stop7h 11m
United Airlines
Deal found 5/1![United Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/113:08 pm
HHH
- BOS
1 stop8h 27m
United Airlines
Tue 5/195:45 am
BOS
- HHH
2 stops8h 26m
United Airlines
Deal found 5/1![United Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 5/1. 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 5/124:16 pm
HHH
- BOS
1 stop6h 09m
Delta
Tue 5/198:00 am
BOS
- HHH
1 stop7h 33m
Delta
Deal found 5/1![Delta logo]()
$271
This Delta deal was found by Cheapflights users on 5/1. 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 5/124:16 pm
HHH
- BOS
1 stop6h 09m
Delta
Mon 5/186:30 pm
BOS
- HHH
1 stop17h 07m
Delta
Deal found 5/1![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 5/1. 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 5/124:16 pm
HHH
- BOS
1 stop6h 09m
Delta
Sat 5/167:00 am
BOS
- HHH
1 stop4h 37m
Delta
Deal found 5/1![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 5/1. 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 5/124:16 pm
HHH
- BOS
1 stop6h 09m
Delta
Wed 5/207:00 am
BOS
- HHH
2 stops8h 33m
Delta
Deal found 5/1![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 5/1. 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 5/1312:18 pm
HHH
- BOS
2 stops10h 07m
Delta
Wed 5/209:10 am
BOS
- HHH
1 stop6h 23m
Delta
Deal found 5/1![Delta logo]()
$276
This Delta deal was found by Cheapflights users on 5/1. 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 5/1312:18 pm
HHH
- BOS
2 stops10h 07m
Delta
Mon 5/186:30 pm
BOS
- HHH
1 stop17h 07m
Delta
Deal found 5/1![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 5/1. 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 5/1312:18 pm
HHH
- BOS
2 stops10h 07m
Delta
Tue 5/197:00 am
BOS
- HHH
2 stops8h 33m
Delta
Deal found 5/1![Delta logo]()
$340
This Delta deal was found by Cheapflights users on 5/1. 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 5/144:16 pm
HHH
- BOS
1 stop14h 59m
Delta
Tue 5/199:10 am
BOS
- HHH
1 stop6h 23m
Delta
Deal found 5/1![Delta logo]()
$347
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 May 4, 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 May 4, 2026.
This Delta deal was found by Cheapflights users on 4/29. 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.
Mon 6/294:15 pm
HHH
- BOS
1 stop7h 12m
Delta
Deal found 4/29![Delta logo]()
$129
This Delta deal was found by Cheapflights users on 4/29. 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.
Sun 7/2612:11 pm
HHH
- BOS
2 stops10h 32m
Delta
Deal found 4/29![Delta logo]()
$134
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/134:39 pm
HHH
- BOS
1 stop5h 35m
United Airlines
Deal found 4/29![United Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 4/29. 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 10/2712:00 pm
HHH
- BOS
2 stops10h 21m
Delta
Deal found 4/29![Delta logo]()
$141
This American Airlines deal was found by Cheapflights users on 5/3. 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 6/63:39 pm
HHH
- BOS
Nonstop2h 38m
American Airlines
Deal found 5/3![American Airlines logo]()
$150
This Delta deal was found by Cheapflights users on 4/29. 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 6/264:15 pm
HHH
- BOS
1 stop7h 12m
Delta
Deal found 4/29![Delta logo]()
$160
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 5/2812:18 pm
HHH
- BOS
2 stops10h 33m
Delta
Deal found 4/29![Delta logo]()
$161
This Delta deal was found by Cheapflights users on 4/29. 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.
Sun 6/2812:13 pm
HHH
- BOS
2 stops10h 28m
Delta
Deal found 4/29![Delta logo]()
$165
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3012:16 pm
HHH
- BOS
Nonstop2h 38m
American Airlines
Deal found 5/1![American Airlines logo]()
$166
This Delta deal was found by Cheapflights users on 5/1. 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 6/254:15 pm
HHH
- BOS
1 stop15h 00m
Delta
Deal found 5/1![Delta logo]()
$172
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/2912:56 pm
HHH
- BOS
1 stop7h 12m
American Airlines
Deal found 4/29![American Airlines logo]()
$176
Find flight deals from Hilton Head Island to Boston
Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to Boston (BOS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $237 (Delta) |
One-way from | $129 (Delta) |
Popular in | April |
Cheapest in | September |
Average price | $519 |
Cheapflights Fare Finder
Customize your flight search to find flights from Hilton Head Island to Boston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 4, 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 6/24
4:15 pm-11:27 pm
1 stop7h 12m
Boston Logan Intl
Thu 7/2
6:00 am-11:31 am
1 stop5h 31m
$237
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Wed 6/24
4:15 pm-11:27 pm
1 stop7h 12m
Boston Logan Intl
Tue 6/30
8:05 am-3:32 pm
1 stop7h 27m
$273
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Thu 6/18
4:15 pm-11:27 pm
1 stop7h 12m
Boston Logan Intl
Mon 6/22
10:00 pm-11:31 am
1 stop13h 31m
$285
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Wed 6/3
11:40 am-6:02 pm
1 stop6h 22m
Boston Logan Intl
Sun 6/7
5:31 am-12:26 pm
2 stops6h 55m
$295
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Thu 5/28
12:18 pm-10:51 pm
2 stops10h 33m
Boston Logan Intl
Thu 6/4
6:00 am-3:33 pm
2 stops9h 33m
$319
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Thu 6/25
4:15 pm-8:21 am
1 stop16h 06m
Boston Logan Intl
Thu 7/2
6:00 am-11:31 am
1 stop5h 31m
$330
Quickest round-trip
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Fri 7/10
12:50 pm-6:04 pm
1 stop5h 14m
Boston Logan Intl
Sun 7/12
6:04 am-12:20 pm
1 stop6h 16m
$370
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Fri 5/15
4:16 pm-10:25 pm
1 stop6h 09m
Boston Logan Intl
Tue 5/19
9:10 am-3:33 pm
1 stop6h 23m
$385
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Sat 5/23
1:45 pm-7:28 pm
1 stop5h 43m
Boston Logan Intl
Sat 5/30
5:45 am-12:52 pm
2 stops7h 07m
$476
Hilton Head IslandBoston
HHH - BOS
HHHBOS
Hilton Head Island
Wed 9/2
1:45 pm-11:54 pm
2 stops10h 09m
Boston Logan Intl
Sat 9/5
5:59 pm-12:52 pm
1 stop18h 53m
$526
Showing 1-10 of 23 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 May 4, 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
Boarding
7.5
Food
6.4
Overall
7.1
Comfort
7.2
Entertainment
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Crew
7.9
Boarding
7.5
Food
6.4
Overall
7.1
Comfort
7.2
Entertainment
6.9
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 locationsMedford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Cranston
Chelsea
Warwick
Peabody
Seabrook
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Waltham
Lowell
Braintree
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Alternative routes for Hilton Head Island to Boston
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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 May 4, 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 May 4, 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 May 4, 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 May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$250 | Average$422 | FlexibilityNo cancel fee | On-time71% |