$284+ Cheap flights from Boston to Hilton Head Island (BOS - HHH)
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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — HHH
Oct 28 — Nov 41
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Boston to Hilton Head Island 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Boston to Hilton Head Island
Cheapest
Best
Last-minute
One-way
Cheapest flights from Boston to Hilton Head IslandExplore the most affordable flight options available from Boston to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 28, 2026.
Explore the most affordable flight options available from Boston to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 28, 2026.
This American Airlines deal was found by Cheapflights users on 9/24. 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 11/37:15 am -
1 stop4h 38m
Wed 11/1112:25 pm -
1 stop6h 45m
Deal found 9/24![American Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 9/26. 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.
Thu 11/1210:12 am -
1 stop6h 58m
Tue 11/174:17 pm -
1 stop5h 33m
Deal found 9/26![American Airlines logo]()
$330
This United Airlines deal was found by Cheapflights users on 9/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am -
1 stop6h 35m
Sat 10/242:51 pm -
1 stop7h 08m
Deal found 9/27![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/27. 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 10/276:00 am -
2 stops9h 30m
Wed 11/412:23 pm -
2 stops10h 01m
Deal found 9/27![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/26. 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 10/207:00 am -
1 stop4h 59m
Sat 10/312:56 pm -
1 stop5h 03m
Deal found 9/26![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 9/23. 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 10/76:00 am -
1 stop4h 25m
Tue 10/1312:29 pm -
1 stop5h 27m
Deal found 9/23![American Airlines logo]()
$393
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Fri 11/137:00 am -
2 stops10h 10m
Fri 11/2011:06 am -
1 stop4h 38m
Deal found 9/28![American Airlines logo]()
$396
Best flights from Boston to Hilton Head IslandDiscover carefully curated flight deals from Boston to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 28, 2026.
Discover carefully curated flight deals from Boston to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 28, 2026.
This American Airlines deal was found by Cheapflights users on 9/23. 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 12/46:00 am -
1 stop4h 34m
Mon 12/712:25 pm -
1 stop6h 45m
Deal found 9/23![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am -
1 stop6h 35m
Sat 10/242:51 pm -
1 stop7h 08m
Deal found 9/27![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/24. 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 10/187:00 am -
1 stop4h 43m
Thu 10/224:13 pm -
1 stop6h 11m
Deal found 9/24![Delta logo]()
$567
This United Airlines deal was found by Cheapflights users on 9/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:38 am -
1 stop4h 57m
Sat 10/171:16 pm -
1 stop6h 09m
Deal found 9/28![United Airlines logo]()
$554
This American Airlines deal was found by Cheapflights users on 9/27. 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 10/16:00 am -
1 stop4h 37m
Sat 10/32:20 pm -
2 stops9h 08m
Deal found 9/27![American Airlines logo]()
$566
This Delta deal was found by Cheapflights users on 9/28. 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 10/196:00 am -
1 stop5h 43m
Wed 10/2112:23 pm -
2 stops10h 57m
Deal found 9/28![Delta logo]()
$572
This Delta deal was found by Cheapflights users on 9/23. 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 10/266:00 am -
2 stops9h 30m
Thu 10/294:13 pm -
1 stop6h 11m
Deal found 9/23![Delta logo]()
$598
This American Airlines deal was found by Cheapflights users on 9/23. 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 11/2010:12 am -
1 stop6h 56m
Fri 11/272:49 pm -
1 stop5h 05m
Deal found 9/23![American Airlines logo]()
$643
This Delta deal was found by Cheapflights users on 9/23. 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 10/26:00 am -
2 stops9h 27m
Sun 10/44:17 pm -
1 stop5h 14m
Deal found 9/23![Delta logo]()
$689
Last-minute flights from Boston to Hilton Head IslandDiscover last-minute flight deals from Boston to Hilton Head Island. Data last updated September 28, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Hilton Head Island. Data last updated September 28, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:00 am -
1 stop6h 35m
Tue 10/61:16 pm -
1 stop4h 36m
Deal found 9/28![United Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Wed 10/76:00 am -
1 stop5h 05m
Wed 10/1410:55 am -
1 stop5h 59m
Deal found 9/28![American Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 9/28. 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 10/76:00 am -
2 stops9h 30m
Wed 10/144:13 pm -
1 stop6h 11m
Deal found 9/28![Delta logo]()
$398
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Tue 10/136:00 am -
1 stop4h 25m
Sat 10/176:13 pm -
1 stop4h 38m
Deal found 9/28![American Airlines logo]()
$418
This Delta deal was found by Cheapflights users on 9/24. 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 10/159:05 am -
1 stop6h 25m
Wed 10/214:13 pm -
1 stop6h 11m
Deal found 9/24![Delta logo]()
$419
This United Airlines deal was found by Cheapflights users on 9/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:00 am -
1 stop6h 35m
Tue 10/201:16 pm -
1 stop4h 36m
Deal found 9/28![United Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 9/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am -
1 stop6h 35m
Sat 10/242:51 pm -
1 stop7h 08m
Deal found 9/27![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/26. 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 10/207:00 am -
1 stop4h 59m
Sat 10/312:56 pm -
1 stop5h 03m
Deal found 9/26![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 9/26. 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 10/236:00 am -
1 stop4h 25m
Sat 10/312:56 pm -
1 stop6h 00m
Deal found 9/26![American Airlines logo]()
$411
This Delta deal was found by Cheapflights users on 9/27. 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 10/276:00 am -
2 stops9h 30m
Wed 11/412:23 pm -
2 stops10h 01m
Deal found 9/27![Delta logo]()
$349
One-way flights from Boston to Hilton Head IslandSearch for one-way flight options from Boston to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.
Search for one-way flight options from Boston to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.
This United Airlines deal was found by Cheapflights users on 9/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:38 am -
1 stop4h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![United Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 9/28. 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.
Sat 10/246:00 am -
2 stops9h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 9/28. 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.
Thu 10/2910:15 am -
1 stop5h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Fri 3/268:00 am -
1 stop7h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 9/28. 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.
Sun 10/256:00 am -
2 stops9h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$315
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Mon 11/2310:12 am -
1 stop6h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 9/27. 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 12/29:21 pm -
2 stops13h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 9/26. 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.
Mon 3/2210:56 am -
1 stop6h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![American Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 9/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:38 am -
1 stop4h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![United Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Mon 11/3010:12 am -
1 stop6h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 9/24. 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 10/239:20 pm -
2 stops18h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Delta logo]()
$405
This United Airlines deal was found by Cheapflights users on 9/24. 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 10/238:50 pm -
2 stops17h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![United Airlines logo]()
$414
Find flight deals from Boston to Hilton Head Island
Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Hilton Head Island (HHH). 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 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $321 (American Airlines) |
One-way from | $284 (American Airlines) |
Popular in | April |
Cheapest in | June |
Average price | $434 |
Good round-trip deal | $463 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Hilton Head Island 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 28, 2026.
Use the filters below to find and compare flights from Boston to Hilton Head Island that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Tue 10/27
6:00 am-11:43 am
1 stop5h 43m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Sat 10/24
7:01 am-2:10 pm
1 stop7h 09m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Mon 11/23
5:40 am-10:36 am
1 stop4h 56m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Fri 10/23
7:38 am-12:35 pm
1 stop4h 57m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Quickest round-trip
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Wed 11/4
7:00 am-11:43 am
1 stop4h 43m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Sat 10/31
10:15 am-3:30 pm
1 stop5h 15m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Wed 10/28
7:00 am-11:43 am
1 stop4h 43m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Mon 10/26
6:00 am-11:43 am
1 stop5h 43m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Fri 12/4
6:00 am-10:34 am
1 stop4h 34m
Hilton Head Island
Mon 12/7
12:25 pm-7:10 pm
1 stop6h 45m
$339
BostonHilton Head Island
BOS Boston Logan Intl - HHH Hilton Head Island
BOSHHH
Boston Logan Intl
Sun 10/18
6:00 am-12:35 pm
1 stop6h 35m
Hilton Head Island
Sat 10/24
2:51 pm-9:59 pm
1 stop7h 08m
$339
Showing 1-10 of 17 resultsSorted by cheapest first
Compare providers for flights from Boston to Hilton Head Island
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 Boston to Hilton Head Island in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Boston-Hilton Head Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Hilton Head Island flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Boston-Hilton Head Island 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 Boston-Hilton Head Island 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 Boston to Hilton Head Island
Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Boston with our price prediction graph.
BOS-HHH
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 Boston to Hilton Head Island
How far ahead should I book a flight from Boston to Hilton Head Island?
The best time to book flights from Boston to Hilton Head Island is 65 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Boston to Hilton Head Island?
Currently, June is the cheapest month in which you can book a flight from Boston to Hilton Head Island (average of $333). Flying from Boston to Hilton Head Island in April is currently the most expensive (average of $574). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Boston to Hilton Head Island?
Airfare is below average for this route at the moment.
Boston to Hilton Head Island flights typically cost between $357 and $557 in November.The cheapest round-trip price found within the last 5 days was $321 on American Airlines (Nov 3-Nov 11).
Reviews of airlines servicing Hilton Head Island
Get insights into the airlines that provide service to Hilton Head Island. 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 Hilton Head Island. Reviews last updated September 28, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andJetBlue from Boston to Hilton Head Island by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Related info for your journey
Find useful and relevant information for your journey from Boston to Hilton Head Island. 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 Hilton Head Island?
Book flights to Hilton Head Island if you plan to visit one of these locationsBeaufort
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Hilton Head Island flight routes
Other flight options
Other flights from Boston
Popular flights
Alternative routes for Boston to Hilton Head Island
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Hilton Head Island by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Hilton Head Island by cabin class
Find flights from Boston to Hilton Head Island, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Hilton Head Island
Explore flights to Hilton Head Island departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 28, 2026.
Boston and Hilton Head Island flights
Browse other Boston and Hilton Head Island flight options. Last updated on September 28, 2026.
Other flights from Boston
Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on September 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Boston to Hilton Head Island
Discover the top 4 airlines that operate flights from Boston to Hilton Head Island. 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 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$183 | Average$355 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$212 | Average$387 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$432 | FlexibilityNo cancel fee | On-time71% |