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Cheap flights from Boston to Hilton Head Island from $104

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Hilton Head Island departing on 12/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Boston to Hilton Head Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
9:45 am - 2:59 pmBOS-HHH
5h 14m1 stop
American Airlines Logo
4:15 pm - 10:19 pmHHH-BOS
6h 04m1 stop
$222American Airlines
Find Deal
Mon, Feb 9 - Sun, Feb 15
American Airlines Logo
8:00 am - 2:59 pmBOS-HHH
6h 59m2 stops
American Airlines Logo
4:15 pm - 10:19 pmHHH-BOS
6h 04m1 stop
$227American Airlines
Find Deal
Mon, Feb 9 - Sun, Feb 15
American Airlines Logo
6:00 am - 2:59 pmBOS-HHH
8h 59m2 stops
American Airlines Logo
11:03 am - 6:04 pmHHH-BOS
7h 01m2 stops
$232American Airlines
Find Deal
Mon, Feb 9 - Sun, Feb 15
American Airlines Logo
6:00 am - 2:57 pmBOS-HHH
8h 57m2 stops
American Airlines Logo
3:27 pm - 10:27 pmHHH-BOS
7h 00m2 stops
$237American Airlines
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Fri, Dec 12 - Tue, Dec 16
American Airlines Logo
8:00 am - 2:59 pmBOS-HHH
6h 59m2 stops
American Airlines Logo
3:29 pm - 10:39 pmHHH-BOS
7h 10m1 stop
$242American Airlines
Find Deal
Sun, Feb 1 - Thu, Feb 5
American Airlines Logo
9:50 am - 2:57 pmBOS-HHH
5h 07m1 stop
American Airlines Logo
2:46 pm - 9:11 pmHHH-BOS
6h 25m1 stop
$243American Airlines
Find Deal
Tue, Dec 16 - Tue, Dec 23
American Airlines Logo
6:00 am - 2:59 pmBOS-HHH
8h 59m2 stops
American Airlines Logo
3:29 pm - 10:56 pmHHH-BOS
7h 27m2 stops
$247American Airlines
Find Deal
Sun, Feb 1 - Thu, Feb 5
American Airlines Logo
6:05 am - 2:57 pmBOS-HHH
8h 52m2 stops
American Airlines Logo
2:46 pm - 9:11 pmHHH-BOS
6h 25m1 stop
$248American Airlines
Find Deal
Tue, Dec 16 - Tue, Dec 23
United Airlines Logo
6:00 am - 1:52 pmBOS-HHH
7h 52m1 stop
United Airlines Logo
3:00 pm - 9:46 pmHHH-BOS
6h 46m1 stop
$328United Airlines
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Sat, Mar 14 - Sat, Mar 21
United Airlines Logo
6:00 am - 1:52 pmBOS-HHH
7h 52m1 stop
United Airlines Logo
3:00 pm - 11:48 pmHHH-BOS
8h 48m2 stops
$333United Airlines
Find Deal
Sat, Mar 14 - Sat, Mar 21

American Airlines flights from Boston to Hilton Head Island

Our best American Airlines deals on Boston to Hilton Head Island flight tickets
American Airlines
Feb 9
BOS9:45 amBoston Logan Intl
5h 14m
1 stop
HHH2:59 pmHilton Head Island
Feb 15
HHH4:15 pmHilton Head Island
6h 04m
1 stop
BOS10:19 pmBoston Logan Intl
$222
Find similar
American Airlines
Feb 9
BOS8:00 amBoston Logan Intl
6h 59m
2 stops
HHH2:59 pmHilton Head Island
Feb 15
HHH4:15 pmHilton Head Island
6h 04m
1 stop
BOS10:19 pmBoston Logan Intl
$227
Find similar
American Airlines
Feb 9
BOS6:00 amBoston Logan Intl
8h 59m
2 stops
HHH2:59 pmHilton Head Island
Feb 15
HHH11:03 amHilton Head Island
7h 01m
2 stops
BOS6:04 pmBoston Logan Intl
$232
Find similar

United Airlines flights from Boston to Hilton Head Island

Our best United Airlines deals on Boston to Hilton Head Island flight tickets
United Airlines
Mar 14
BOS6:00 amBoston Logan Intl
7h 52m
1 stop
HHH1:52 pmHilton Head Island
Mar 21
HHH3:00 pmHilton Head Island
6h 46m
1 stop
BOS9:46 pmBoston Logan Intl
$328
Find similar
United Airlines
Mar 14
BOS6:00 amBoston Logan Intl
7h 52m
1 stop
HHH1:52 pmHilton Head Island
Mar 21
HHH3:00 pmHilton Head Island
8h 48m
2 stops
BOS11:48 pmBoston Logan Intl
$333
Find similar
United Airlines
Apr 20
BOS6:00 amBoston Logan Intl
7h 52m
1 stop
HHH1:52 pmHilton Head Island
Apr 30
HHH3:00 pmHilton Head Island
6h 33m
1 stop
BOS9:33 pmBoston Logan Intl
$398
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated November 3, 2025.
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

Price

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

9:45 am-2:59 pm

1 stop5h 14m

Hilton Head Island

Sun 2/15

4:15 pm-10:19 pm

1 stop6h 04m

$222

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

8:00 am-2:59 pm

2 stops6h 59m

Hilton Head Island

Sun 2/15

4:15 pm-10:19 pm

1 stop6h 04m

$227

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

6:00 am-2:59 pm

2 stops8h 59m

Hilton Head Island

Sun 2/15

11:03 am-6:04 pm

2 stops7h 01m

$232

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 12/12

6:00 am-2:57 pm

2 stops8h 57m

Hilton Head Island

Tue 12/16

3:27 pm-10:27 pm

2 stops7h 00m

$237

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 2/1

8:00 am-2:59 pm

2 stops6h 59m

Hilton Head Island

Thu 2/5

3:29 pm-10:39 pm

1 stop7h 10m

$242

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 12/16

9:50 am-2:57 pm

1 stop5h 07m

Hilton Head Island

Tue 12/23

2:46 pm-9:11 pm

1 stop6h 25m

$243

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 2/1

6:00 am-2:59 pm

2 stops8h 59m

Hilton Head Island

Thu 2/5

3:29 pm-10:56 pm

2 stops7h 27m

$247

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 12/16

6:05 am-2:57 pm

2 stops8h 52m

Hilton Head Island

Tue 12/23

2:46 pm-9:11 pm

1 stop6h 25m

$248

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 3/14

6:00 am-1:52 pm

1 stop7h 52m

Hilton Head Island

Sat 3/21

3:00 pm-9:46 pm

1 stop6h 46m

$328

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 3/14

6:00 am-1:52 pm

1 stop7h 52m

Hilton Head Island

Sat 3/21

3:00 pm-11:48 pm

2 stops8h 48m

$333

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Hilton Head Island from

How to get the cheapest flight ticket from Boston to Hilton Head Island

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Hilton Head Island?

If you don’t want to visit Hilton Head Island in December, then you should wait until January to fly from Boston, when ticket prices are also cheap, with an average price of $268.

What is the cheapest day to depart on your flight to Hilton Head Island?

The cheapest day to depart from Boston to Hilton Head Island is on a Saturday. Travelers who choose to depart for Hilton Head Island on a Saturday will often find tickets for as low as $315. On the other hand, Thursday is the most expensive day to depart from Boston because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $573.

What is the cheapest time of day to depart on your flight to Hilton Head Island?

Flying to Hilton Head Island from Boston in the evening is the least expensive time of day to depart. momondo users have found prices as low as $138 when looking at flights departing in the evening. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $315 on average. Flights to Hilton Head Island from Boston in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Boston Logan Intl to Hilton Head Island flight route?

Fly from Boston Logan Intl to Hilton Head Island for the best Boston Logan Intl - Hilton Head Island flight prices

How far in advance should I book a flight to Hilton Head Island?

You are more likely to see cheaper flights to Hilton Head Island from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Hilton Head Island for around $357 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Hilton Head Island from Boston for as low as $299 on momondo.

What cabin class options are available on Boston Logan Intl to Hilton Head Island flights?

There is only 1 cabin class available to choose from on Boston Logan Intl to Hilton Head Island flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Boston to Hilton Head Island flights?

You could potentially save up to 23% on your flight if you consider stops on a Boston to Hilton Head Island flight.

How have Boston to Hilton Head Island flight prices changed over time?

As of November 2025, prices for Boston to Hilton Head Island flights are approximately 133% more expensive when compared to flights at the same time last year.

When to book flights from Boston to Hilton Head Island

Are you open to changing your travel dates? Check out the ideal times to fly from Boston to Hilton Head Island according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Boston to Hilton Head Island (BOS to HHH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Boston to Hilton Head Island

Direct flights

None
There are no direct flights from Boston to Hilton Head Island. There are no popular flight routes from Boston to Hilton Head Island.
Search flight deals

  • How far is Boston Logan Intl to Hilton Head Island by plane?

    A flight from Boston Logan Intl to Hilton Head Island will travel around 878.6 mi. In terms of flight time, this usually takes a little over 4h 18m.

  • When did momondo last update prices for flights from Boston Logan Intl Airport to Hilton Head Island Airport?

    Prices for flights from Boston Logan Intl Airport to Hilton Head Island Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Boston Logan Intl Airport to Hilton Head Island Airport?

  • How old do you have to be to fly from Boston Logan Intl Airport to Hilton Head Island Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Boston Logan Intl Airport to Hilton Head Island Airport.

  • What documentation or ID do you need to fly to Hilton Head Island Airport?

    The required travel and health documents for your Hilton Head Island Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Hilton Head Island Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Boston to Hilton Head Island?

  • What is the most popular airline from Boston to Hilton Head Island?

Best airlines flying from Boston to Hilton Head Island

Compare and see reviews for airlines that fly from Boston to Hilton Head Island with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $167Free CancellationRating
7.2
2,907 reviews
Search JetBlue flights
DeltaPriceFrom $167Free CancellationRating
7.9
8,001 reviews
Search Delta flights
American AirlinesPriceFrom $255Free CancellationRating
7.2
11,036 reviews
Search American Airlines flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton
Daufuskie Island

Why use momondo?

Why should I use momondo to find a flight deal from Boston to Hilton Head Island?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Boston to Hilton Head Island for you.

Can I find flights from Boston to Hilton Head Island with flexible booking policies on momondo?

Yes. All flights to Hilton Head Island from Boston on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Boston to Hilton Head Island?

momondo provides multiple filters to help you find the best flight to Hilton Head Island from Boston. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Boston to Hilton Head Island right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Boston to Hilton Head Island flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Hilton Head Island trip

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