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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 3/4. 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

Enter your travel dates to find the best prices.
American Airlines Logo
10:00 am - 4:44 pm
BOS
-
HHH
6h 44m
1 stop
American Airlines Logo
3:31 pm - 10:15 pm
HHH
-
BOS
6h 44m
1 stop
$251American Airlines
Tue, Feb 24 - Tue, Mar 3
American Airlines Logo
8:00 am - 3:41 pm
BOS
-
HHH
7h 41m
1 stop
American Airlines Logo
3:31 pm - 10:24 pm
HHH
-
BOS
6h 53m
2 stops
$256American Airlines
Tue, Feb 24 - Tue, Mar 3
American Airlines Logo
7:45 am - 3:01 pm
BOS
-
HHH
7h 16m
2 stops
American Airlines Logo
5:19 pm - 11:23 pm
HHH
-
BOS
6h 04m
2 stops
$261American Airlines
Tue, Feb 24 - Tue, Mar 3
American Airlines Logo
5:47 am - 10:33 am
BOS
-
HHH
4h 46m
1 stop
American Airlines Logo
4:11 pm - 10:22 pm
HHH
-
BOS
6h 11m
1 stop
$277American Airlines
Sun, Mar 1 - Fri, Mar 6
American Airlines Logo
10:56 am - 5:44 pm
BOS
-
HHH
6h 48m
1 stop
American Airlines Logo
6:15 pm - 11:59 pm
HHH
-
BOS
5h 44m
2 stops
$282American Airlines
Mon, Mar 2 - Mon, Mar 9
American Airlines Logo
8:00 am - 5:44 pm
BOS
-
HHH
9h 44m
2 stops
American Airlines Logo
6:15 pm - 11:59 pm
HHH
-
BOS
5h 44m
2 stops
$287American Airlines
Mon, Mar 2 - Mon, Mar 9
American Airlines Logo
7:15 am - 11:53 am
BOS
-
HHH
4h 38m
1 stop
American Airlines Logo
4:11 pm - 10:22 pm
HHH
-
BOS
6h 11m
1 stop
$288American Airlines
Tue, Mar 24 - Mon, Mar 30
American Airlines Logo
9:00 am - 3:41 pm
BOS
-
HHH
6h 41m
1 stop
American Airlines Logo
4:11 pm - 10:22 pm
HHH
-
BOS
6h 11m
1 stop
$297American Airlines
Wed, Mar 25 - Thu, Mar 26
American Airlines Logo
6:00 am - 10:33 am
BDL
-
HHH
4h 33m
1 stop
American Airlines Logo
3:31 pm - 10:44 pm
HHH
-
BDL
7h 13m
1 stop
$307American Airlines
Thu, Feb 26 - Tue, Mar 3
American Airlines Logo
8:05 am - 3:41 pm
BOS
-
HHH
7h 36m
1 stop
American Airlines Logo
4:31 pm - 10:22 pm
HHH
-
BOS
5h 51m
1 stop
$308American Airlines
Sun, Mar 1 - Sat, Mar 7

United Airlines flights from Massachusetts to Hilton Head Island

Our best United Airlines deals on Massachusetts to Hilton Head Island flight tickets
United Airlines
May 29
BOS6:00 amBoston Logan Intl
6h 52m
1 stop
HHH12:52 pmHilton Head Island
Jun 5
HHH3:00 pmHilton Head Island
8h 16m
1 stop
BOS11:16 pmBoston Logan Intl
$389
United Airlines
Apr 27
BDL6:00 amHartford Bradley Intl
8h 06m
2 stops
HHH2:06 pmHilton Head Island
Apr 29
HHH4:11 pmHilton Head Island
7h 48m
2 stops
BDL11:59 pmHartford Bradley Intl
$468
United Airlines
May 29
BOS8:00 amBoston Logan Intl
4h 52m
1 stop
HHH12:52 pmHilton Head Island
Jun 5
HHH3:00 pmHilton Head Island
22h 36m
2 stops
BOS1:36 pmBoston Logan Intl
$472

American Airlines flights from Massachusetts to Hilton Head Island

Our best American Airlines deals on Massachusetts to Hilton Head Island flight tickets
American Airlines
Feb 24
BOS10:00 amBoston Logan Intl
6h 44m
1 stop
HHH4:44 pmHilton Head Island
Mar 3
HHH3:31 pmHilton Head Island
6h 44m
1 stop
BOS10:15 pmBoston Logan Intl
$251
American Airlines
Feb 24
BOS8:00 amBoston Logan Intl
7h 41m
1 stop
HHH3:41 pmHilton Head Island
Mar 3
HHH3:31 pmHilton Head Island
6h 53m
2 stops
BOS10:24 pmBoston Logan Intl
$256
American Airlines
Feb 24
BOS7:45 amBoston Logan Intl
7h 16m
2 stops
HHH3:01 pmHilton Head Island
Mar 3
HHH5:19 pmHilton Head Island
6h 04m
2 stops
BOS11:23 pmBoston Logan Intl
$261

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 February 4, 2026.
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

Tue 2/24

10:00 am-4:44 pm

1 stop6h 44m

Hilton Head Island

Tue 3/3

3:31 pm-10:15 pm

1 stop6h 44m

$251

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 2/24

8:00 am-3:41 pm

1 stop7h 41m

Hilton Head Island

Tue 3/3

3:31 pm-10:24 pm

2 stops6h 53m

$256

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 2/24

7:45 am-3:01 pm

2 stops7h 16m

Hilton Head Island

Tue 3/3

5:19 pm-11:23 pm

2 stops6h 04m

$261

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 3/1

5:47 am-10:33 am

1 stop4h 46m

Hilton Head Island

Fri 3/6

4:11 pm-10:22 pm

1 stop6h 11m

$277

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 3/2

10:56 am-5:44 pm

1 stop6h 48m

Hilton Head Island

Mon 3/9

6:15 pm-11:59 pm

2 stops5h 44m

$282

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 3/2

8:00 am-5:44 pm

2 stops9h 44m

Hilton Head Island

Mon 3/9

6:15 pm-11:59 pm

2 stops5h 44m

$287

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 3/24

7:15 am-11:53 am

1 stop4h 38m

Hilton Head Island

Mon 3/30

4:11 pm-10:22 pm

1 stop6h 11m

$288

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 3/25

9:00 am-3:41 pm

1 stop6h 41m

Hilton Head Island

Thu 3/26

4:11 pm-10:22 pm

1 stop6h 11m

$297

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Thu 2/26

6:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Tue 3/3

3:31 pm-10:44 pm

1 stop7h 13m

$307

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sun 3/1

8:05 am-3:41 pm

1 stop7h 36m

Hilton Head Island

Sat 3/7

4:31 pm-10:22 pm

1 stop5h 51m

$308

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 December, then you should wait until November to fly from Massachusetts, when ticket prices are also cheap, with an average price of $302.

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 $359 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 is only 1 cabin class 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 3% 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

Fastest flight time

2h 32m

Direct flights

None
The fastest flight from Massachusetts to Hilton Head Island takes 2h 32m
There are no direct flights from Massachusetts to Hilton Head Island. There are no popular flight routes from Massachusetts to Hilton Head Island.
Search flight deals

  • 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 $167Free CancellationRating
7.2
2,893 reviews
Search JetBlue flights
DeltaPriceFrom $167Free CancellationRating
7.9
8,138 reviews
Search Delta flights
United AirlinesPriceFrom $183Free CancellationRating
7.4
9,236 reviews
Search United Airlines flights
American AirlinesPriceFrom $258Free CancellationRating
7.2
11,216 reviews
Search American 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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