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Cheap flights from Massachusetts to Hilton Head Island from $179

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 5/19. 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.
United Airlines Logo
10:05 am - 3:30 pm
BOS
-
HHH
5h 25m
1 stop
United Airlines Logo
4:11 pm - 9:54 pm
HHH
-
BOS
5h 43m
1 stop
$334United Airlines
Tue, Apr 7 - Tue, Apr 14
United Airlines Logo
5:45 am - 3:30 pm
BOS
-
HHH
9h 45m
2 stops
United Airlines Logo
4:11 pm - 9:54 pm
HHH
-
BOS
5h 43m
1 stop
$339United Airlines
Tue, Apr 7 - Tue, Apr 14
Delta Logo
8:00 am - 3:20 pm
BDL
-
HHH
7h 20m
1 stop
Delta Logo
12:18 pm - 6:45 pm
HHH
-
BDL
6h 27m
1 stop
$344Delta
Tue, May 5 - Sat, May 9
United Airlines Logo
5:45 am - 2:16 pm
BOS
-
HHH
8h 31m
2 stops
United Airlines Logo
4:11 pm - 11:59 pm
HHH
-
BOS
7h 48m
2 stops
$344United Airlines
Tue, Apr 7 - Tue, Apr 14
United Airlines Logo
10:00 am - 3:41 pm
BOS
-
HHH
5h 41m
1 stop
United Airlines Logo
3:08 pm - 11:59 pm
HHH
-
BOS
8h 51m
2 stops
$348United Airlines
Sat, May 2 - Tue, May 5
Delta Logo
5:30 am - 3:20 pm
BDL
-
HHH
9h 50m
2 stops
Delta Logo
12:18 pm - 6:45 pm
HHH
-
BDL
6h 27m
1 stop
$349Delta
Tue, May 5 - Sat, May 9
American Airlines Logo
7:35 am - 2:13 pm
BDL
-
HHH
6h 38m
1 stop
American Airlines Logo
4:24 pm - 10:02 pm
HHH
-
BDL
5h 38m
1 stop
$352American Airlines
Wed, May 27 - Sat, May 30
American Airlines Logo
7:00 am - 4:32 pm
BDL
-
HHH
9h 32m
2 stops
American Airlines Logo
4:24 pm - 10:02 pm
HHH
-
BDL
5h 38m
1 stop
$357American Airlines
Wed, May 27 - Sat, May 30
Delta Logo
6:00 am - 11:28 am
BOS
-
HHH
5h 28m
1 stop
Delta Logo
4:00 pm - 10:26 pm
HHH
-
BOS
6h 26m
1 stop
$357Delta
Tue, Apr 28 - Wed, May 6
American Airlines Logo
8:14 am - 3:14 pm
BDL
-
HHH
7h 00m
1 stop
American Airlines Logo
2:43 pm - 9:45 pm
HHH
-
BDL
7h 02m
1 stop
$372American Airlines
Tue, May 12 - Fri, May 22

United Airlines flights from Massachusetts to Hilton Head Island

Our best United Airlines deals on Massachusetts to Hilton Head Island flight tickets
United Airlines
Apr 7
BOS10:05 amBoston Logan Intl
5h 25m
1 stop
HHH3:30 pmHilton Head Island
Apr 14
HHH4:11 pmHilton Head Island
5h 43m
1 stop
BOS9:54 pmBoston Logan Intl
$334
United Airlines
Apr 7
BOS5:45 amBoston Logan Intl
9h 45m
2 stops
HHH3:30 pmHilton Head Island
Apr 14
HHH4:11 pmHilton Head Island
5h 43m
1 stop
BOS9:54 pmBoston Logan Intl
$339
United Airlines
Apr 7
BOS5:45 amBoston Logan Intl
8h 31m
2 stops
HHH2:16 pmHilton Head Island
Apr 14
HHH4:11 pmHilton Head Island
7h 48m
2 stops
BOS11:59 pmBoston Logan Intl
$344

Delta flights from Massachusetts to Hilton Head Island

Our best Delta deals on Massachusetts to Hilton Head Island flight tickets
Delta
May 5
BDL8:00 amHartford Bradley Intl
7h 20m
1 stop
HHH3:20 pmHilton Head Island
May 9
HHH12:18 pmHilton Head Island
6h 27m
1 stop
BDL6:45 pmHartford Bradley Intl
$344
Delta
May 5
BDL5:30 amHartford Bradley Intl
9h 50m
2 stops
HHH3:20 pmHilton Head Island
May 9
HHH12:18 pmHilton Head Island
6h 27m
1 stop
BDL6:45 pmHartford Bradley Intl
$349
Delta
Apr 28
BOS6:00 amBoston Logan Intl
5h 28m
1 stop
HHH11:28 amHilton Head Island
May 6
HHH4:00 pmHilton Head Island
6h 26m
1 stop
BOS10:26 pmBoston Logan Intl
$357

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 March 23, 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

Cheapest round-trip
Quickest round-trip

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 4/7

10:05 am-3:30 pm

1 stop5h 25m

Hilton Head Island

Tue 4/14

4:11 pm-9:54 pm

1 stop5h 43m

$334

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 4/7

5:45 am-3:30 pm

2 stops9h 45m

Hilton Head Island

Tue 4/14

4:11 pm-9:54 pm

1 stop5h 43m

$339

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Tue 5/5

8:00 am-3:20 pm

1 stop7h 20m

Hilton Head Island

Sat 5/9

12:18 pm-6:45 pm

1 stop6h 27m

$344

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 4/7

5:45 am-2:16 pm

2 stops8h 31m

Hilton Head Island

Tue 4/14

4:11 pm-11:59 pm

2 stops7h 48m

$344

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 5/2

10:00 am-3:41 pm

1 stop5h 41m

Hilton Head Island

Tue 5/5

3:08 pm-11:59 pm

2 stops8h 51m

$348

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Tue 5/5

5:30 am-3:20 pm

2 stops9h 50m

Hilton Head Island

Sat 5/9

12:18 pm-6:45 pm

1 stop6h 27m

$349

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Wed 5/27

7:35 am-2:13 pm

1 stop6h 38m

Hilton Head Island

Sat 5/30

4:24 pm-10:02 pm

1 stop5h 38m

$352

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Wed 5/27

7:00 am-4:32 pm

2 stops9h 32m

Hilton Head Island

Sat 5/30

4:24 pm-10:02 pm

1 stop5h 38m

$357

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 4/28

6:00 am-11:28 am

1 stop5h 28m

Hilton Head Island

Wed 5/6

4:00 pm-10:26 pm

1 stop6h 26m

$357

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Tue 5/12

8:14 am-3:14 pm

1 stop7h 00m

Hilton Head Island

Fri 5/22

2:43 pm-9:45 pm

1 stop7h 02m

$372

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 22% 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

$383

Fastest flight time

2h 51m

Direct flights

Sun

Airports in Hilton Head Island

1 airport
The best flight deal from Massachusetts to Hilton Head Island found on momondo in the last 72 hours is $383
The fastest flight from Massachusetts to Hilton Head Island takes 2h 51m
Direct flights go from Massachusetts to Hilton Head Island on Sunday. There are no airlines offering direct flights.
There is 1 airport in Hilton Head Island. From Massachusetts there are direct flights to Hilton Head Island (HHH).
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
2,908 reviews
Search JetBlue flights
DeltaPriceFrom $167Free CancellationRating
7.9
8,319 reviews
Search Delta flights
United AirlinesPriceFrom $183Free CancellationRating
7.4
9,462 reviews
Search United Airlines flights
American AirlinesPriceFrom $258Free CancellationRating
7.1
11,488 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

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