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Cheap flights from Massachusetts to Hilton Head Island from $126

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Hilton Head Island departing on 10/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Massachusetts to Hilton Head Island

Cheap round-trip flights

Delta Logo
8:05 am - 3:22 pmBOS-HHH
7h 17m1 stop
Delta Logo
4:05 pm - 10:20 pmHHH-BOS
6h 15m1 stop
$243Delta
Find Deal
Sun, Aug 31 - Fri, Sep 12
Delta Logo
8:05 am - 3:22 pmBOS-HHH
7h 17m1 stop
Delta Logo
12:11 pm - 7:45 pmHHH-BOS
7h 34m2 stops
$248Delta
Find Deal
Sun, Aug 31 - Wed, Sep 10
American Airlines Logo
5:15 am - 10:34 amBDL-HHH
5h 19m1 stop
American Airlines Logo
5:20 pm - 11:29 pmHHH-BDL
6h 09m1 stop
$249American Airlines
Find Deal
Thu, Sep 11 - Mon, Sep 15
Delta Logo
6:00 am - 11:31 amBOS-HHH
5h 31m1 stop
Delta Logo
4:02 pm - 10:24 pmHHH-BOS
6h 22m1 stop
$249Delta
Find Deal
Mon, Sep 1 - Tue, Sep 9
Delta Logo
9:00 am - 3:22 pmBOS-HHH
6h 22m2 stops
Delta Logo
12:11 pm - 4:53 pmHHH-BOS
4h 42m1 stop
$254Delta
Find Deal
Wed, Sep 3 - Tue, Sep 9
American Airlines Logo
6:58 am - 11:59 amBOS-HHH
5h 01m1 stop
American Airlines Logo
3:41 pm - 6:16 pmHHH-BOS
2h 35mnonstop
$257American Airlines
Find Deal
Tue, Aug 26 - Sat, Aug 30
American Airlines Logo
7:50 am - 3:05 pmBOS-HHH
7h 15m2 stops
American Airlines Logo
3:41 pm - 6:16 pmHHH-BOS
2h 35mnonstop
$267American Airlines
Find Deal
Tue, Aug 26 - Sat, Aug 30
United Airlines Logo
6:00 am - 11:21 amBOS-HHH
5h 21m1 stop
United Airlines Logo
12:06 pm - 6:55 pmHHH-BOS
6h 49m2 stops
$318United Airlines
Find Deal
Sun, Aug 31 - Mon, Sep 8
United Airlines Logo
6:00 am - 11:25 amBOS-HHH
5h 25m1 stop
United Airlines Logo
12:06 pm - 5:18 pmHHH-BOS
5h 12m1 stop
$319United Airlines
Find Deal
Sat, Sep 6 - Wed, Sep 10
United Airlines Logo
6:00 am - 11:25 amBOS-HHH
5h 25m1 stop
United Airlines Logo
12:06 pm - 6:55 pmHHH-BOS
6h 49m2 stops
$324United Airlines
Find Deal
Sat, Sep 6 - Tue, Sep 9

Delta flights from Massachusetts to Hilton Head Island

Our best Delta deals on Massachusetts to Hilton Head Island flight tickets
Delta
Aug 31
BOS8:05 amBoston Logan Intl
7h 17m
1 stop
HHH3:22 pmHilton Head Island
Sep 12
HHH4:05 pmHilton Head Island
6h 15m
1 stop
BOS10:20 pmBoston Logan Intl
$243
Find similar
Delta
Aug 31
BOS8:05 amBoston Logan Intl
7h 17m
1 stop
HHH3:22 pmHilton Head Island
Sep 10
HHH12:11 pmHilton Head Island
7h 34m
2 stops
BOS7:45 pmBoston Logan Intl
$248
Find similar
Delta
Sep 1
BOS6:00 amBoston Logan Intl
5h 31m
1 stop
HHH11:31 amHilton Head Island
Sep 9
HHH4:02 pmHilton Head Island
6h 22m
1 stop
BOS10:24 pmBoston Logan Intl
$249
Find similar

American Airlines flights from Massachusetts to Hilton Head Island

Our best American Airlines deals on Massachusetts to Hilton Head Island flight tickets
American Airlines
Sep 11
BDL5:15 amHartford Bradley Intl
5h 19m
1 stop
HHH10:34 amHilton Head Island
Sep 15
HHH5:20 pmHilton Head Island
6h 09m
1 stop
BDL11:29 pmHartford Bradley Intl
$249
Find similar
American Airlines
Aug 26
BOS6:58 amBoston Logan Intl
5h 01m
1 stop
HHH11:59 amHilton Head Island
Aug 30
HHH3:41 pmHilton Head Island
2h 35m
BOS6:16 pmBoston Logan Intl
$257
Find similar
American Airlines
Aug 26
BOS7:50 amBoston Logan Intl
7h 15m
2 stops
HHH3:05 pmHilton Head Island
Aug 30
HHH3:41 pmHilton Head Island
2h 35m
BOS6:16 pmBoston Logan Intl
$267
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts 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 August 11, 2025.
Use the filters below to find and compare flights from Massachusetts 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

Sun 8/31

8:05 am-3:22 pm

1 stop7h 17m

Hilton Head Island

Fri 9/12

4:05 pm-10:20 pm

1 stop6h 15m

$243

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 8/31

8:05 am-3:22 pm

1 stop7h 17m

Hilton Head Island

Wed 9/10

12:11 pm-7:45 pm

2 stops7h 34m

$248

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Thu 9/11

5:15 am-10:34 am

1 stop5h 19m

Hilton Head Island

Mon 9/15

5:20 pm-11:29 pm

1 stop6h 09m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 9/1

6:00 am-11:31 am

1 stop5h 31m

Hilton Head Island

Tue 9/9

4:02 pm-10:24 pm

1 stop6h 22m

$249

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 9/3

9:00 am-3:22 pm

2 stops6h 22m

Hilton Head Island

Tue 9/9

12:11 pm-4:53 pm

1 stop4h 42m

$254

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 8/26

6:58 am-11:59 am

1 stop5h 01m

Hilton Head Island

Sat 8/30

3:41 pm-6:16 pm

Nonstop2h 35m

$257

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 8/26

7:50 am-3:05 pm

2 stops7h 15m

Hilton Head Island

Sat 8/30

3:41 pm-6:16 pm

Nonstop2h 35m

$267

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 8/31

6:00 am-11:21 am

1 stop5h 21m

Hilton Head Island

Mon 9/8

12:06 pm-6:55 pm

2 stops6h 49m

$318

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 9/6

6:00 am-11:25 am

1 stop5h 25m

Hilton Head Island

Wed 9/10

12:06 pm-5:18 pm

1 stop5h 12m

$319

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 9/6

6:00 am-11:25 am

1 stop5h 25m

Hilton Head Island

Tue 9/9

12:06 pm-6:55 pm

2 stops6h 49m

$324

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 Massachusetts 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 January, then you should wait until October to fly from Massachusetts, when ticket prices are also cheap, with an average price of $358.

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

The cheapest day to depart from Massachusetts 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 $321. On the other hand, Thursday is the most expensive day to depart from Massachusetts 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 Massachusetts 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 Massachusetts in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Massachusetts to Hilton Head Island flight route?

Fly from Boston Logan Intl to Hilton Head Island for the best Massachusetts - 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 Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Hilton Head Island for around $423 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 Massachusetts for as low as $299 on momondo.

What cabin class options are available on Massachusetts to Hilton Head Island flights?

There are 1 cabin classes available to choose from on Massachusetts 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 Massachusetts to Hilton Head Island flights?

You could potentially save up to 18% on your flight if you consider stops on a Massachusetts to Hilton Head Island flight.

Cheap Massachusetts to Hilton Head Island flight deals and tips

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

Best Price Found

$126

Fastest flight time

2h 46m

Direct flights

None

Airports in Hilton Head Island

1 airport
The best one-way flight to Hilton Head Island from Massachusetts in the past 72 hours is $126. The best round-trip flight deal from Massachusetts to Hilton Head Island found on momondo in the last 72 hours is $243.
The fastest flight from Massachusetts to Hilton Head Island takes 2h 46m
There are no direct flights from Massachusetts to Hilton Head Island. Popular non-direct routes for this connection are Hartford Bradley Intl Airport - Hilton Head Island Airport and Boston Logan Intl Airport - Hilton Head Island Airport.
There is 1 airport near Hilton Head Island: Hilton Head Island (HHH)
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  • When did momondo last update prices for flights from Massachusetts to Hilton Head Island Airport?

    Prices for flights from Massachusetts to Hilton Head Island Airport refresh daily.

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

  • How old do you have to be to fly from Massachusetts to Hilton Head Island Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Hilton Head Island Airport.

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

    The necessary travel and health documents for your Hilton Head Island Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Massachusetts to Hilton Head Island

Compare and see reviews for airlines that fly from Massachusetts to Hilton Head Island with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $133Free CancellationRating
7.2
2,916 reviews
Search JetBlue flights
DeltaPriceFrom $167Free CancellationRating
8.0
7,979 reviews
Search Delta flights
American AirlinesPriceFrom $262Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
8,920 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 Massachusetts to Hilton Head Island?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Massachusetts to Hilton Head Island. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Massachusetts to Hilton Head Island with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo helps you find the best flight between Massachusetts and Hilton Head Island by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Massachusetts to Hilton Head Island flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Hilton Head Island trip

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