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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 5/30. 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.
Delta Logo
6:00 am - 11:31 am
BOS
-
HHH
5h 31m
1 stop
Delta Logo
4:15 pm - 10:28 pm
HHH
-
BOS
6h 13m
1 stop
$237Delta
Tue, Jun 16 - Tue, Jun 23
Delta Logo
6:06 am - 3:32 pm
BOS
-
HHH
9h 26m
2 stops
Delta Logo
4:15 pm - 10:28 pm
HHH
-
BOS
6h 13m
1 stop
$242Delta
Tue, Jun 16 - Tue, Jun 23
Delta Logo
10:16 am - 3:33 pm
BOS
-
HHH
5h 17m
1 stop
Delta Logo
4:15 pm - 10:28 pm
HHH
-
BOS
6h 13m
1 stop
$254Delta
Tue, Jun 2 - Thu, Jun 11
Delta Logo
7:00 am - 3:33 pm
BOS
-
HHH
8h 33m
2 stops
Delta Logo
4:15 pm - 10:28 pm
HHH
-
BOS
6h 13m
1 stop
$259Delta
Tue, Jun 2 - Thu, Jun 11
American Airlines Logo
12:10 pm - 3:09 pm
BOS
-
HHH
2h 59mnonstop
American Airlines Logo
11:40 am - 3:55 pm
HHH
-
BOS
4h 15m
1 stop
$261American Airlines
Sat, Jun 13 - Tue, Jun 16
American Airlines Logo
8:47 am - 11:46 am
BOS
-
HHH
2h 59mnonstop
American Airlines Logo
3:39 pm - 6:17 pm
HHH
-
BOS
2h 38mnonstop
$270American Airlines
Sat, May 30 - Sat, Jun 6
Delta Logo
10:16 am - 3:33 pm
BOS
-
HHH
5h 17m
1 stop
Delta Logo
4:15 pm - 11:27 pm
HHH
-
BOS
7h 12m
1 stop
$271Delta
Tue, Jun 2 - Wed, Jun 10
American Airlines Logo
12:10 pm - 3:09 pm
BOS
-
HHH
2h 59mnonstop
American Airlines Logo
2:43 pm - 8:59 pm
HHH
-
BOS
6h 16m
1 stop
$273American Airlines
Sat, Jun 13 - Tue, Jun 16
United Airlines Logo
6:00 am - 2:11 pm
BDL
-
HHH
8h 11m
1 stop
United Airlines Logo
3:08 pm - 9:25 pm
HHH
-
BDL
6h 17m
1 stop
$364United Airlines
Tue, May 12 - Mon, May 18
United Airlines Logo
6:05 am - 3:41 pm
BDL
-
HHH
9h 36m
2 stops
United Airlines Logo
3:08 pm - 9:25 pm
HHH
-
BDL
6h 17m
1 stop
$369United Airlines
Tue, May 12 - Mon, May 18

American Airlines flights from Massachusetts to Hilton Head Island

Our best American Airlines deals on Massachusetts to Hilton Head Island flight tickets
American Airlines
Jun 13
BOS12:10 pmBoston Logan Intl
2h 59m
HHH3:09 pmHilton Head Island
Jun 16
HHH11:40 amHilton Head Island
4h 15m
1 stop
BOS3:55 pmBoston Logan Intl
$261
American Airlines
May 30
BOS8:47 amBoston Logan Intl
2h 59m
HHH11:46 amHilton Head Island
Jun 6
HHH3:39 pmHilton Head Island
2h 38m
BOS6:17 pmBoston Logan Intl
$270
American Airlines
Jun 13
BOS12:10 pmBoston Logan Intl
2h 59m
HHH3:09 pmHilton Head Island
Jun 16
HHH2:43 pmHilton Head Island
6h 16m
1 stop
BOS8:59 pmBoston Logan Intl
$273

Delta flights from Massachusetts to Hilton Head Island

Our best Delta deals on Massachusetts to Hilton Head Island flight tickets
Delta
Jun 16
BOS6:00 amBoston Logan Intl
5h 31m
1 stop
HHH11:31 amHilton Head Island
Jun 23
HHH4:15 pmHilton Head Island
6h 13m
1 stop
BOS10:28 pmBoston Logan Intl
$237
Delta
Jun 16
BOS6:06 amBoston Logan Intl
9h 26m
2 stops
HHH3:32 pmHilton Head Island
Jun 23
HHH4:15 pmHilton Head Island
6h 13m
1 stop
BOS10:28 pmBoston Logan Intl
$242
Delta
Jun 2
BOS10:16 amBoston Logan Intl
5h 17m
1 stop
HHH3:33 pmHilton Head Island
Jun 11
HHH4:15 pmHilton Head Island
6h 13m
1 stop
BOS10:28 pmBoston Logan Intl
$254

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 May 7, 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

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 6/16

6:00 am-11:31 am

1 stop5h 31m

Hilton Head Island

Tue 6/23

4:15 pm-10:28 pm

1 stop6h 13m

$237

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 6/16

6:06 am-3:32 pm

2 stops9h 26m

Hilton Head Island

Tue 6/23

4:15 pm-10:28 pm

1 stop6h 13m

$242

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 6/2

10:16 am-3:33 pm

1 stop5h 17m

Hilton Head Island

Thu 6/11

4:15 pm-10:28 pm

1 stop6h 13m

$254

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 6/2

7:00 am-3:33 pm

2 stops8h 33m

Hilton Head Island

Thu 6/11

4:15 pm-10:28 pm

1 stop6h 13m

$259

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 6/13

12:10 pm-3:09 pm

Nonstop2h 59m

Hilton Head Island

Tue 6/16

11:40 am-3:55 pm

1 stop4h 15m

$261
Quickest round-trip

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 5/30

8:47 am-11:46 am

Nonstop2h 59m

Hilton Head Island

Sat 6/6

3:39 pm-6:17 pm

Nonstop2h 38m

$270

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 6/2

10:16 am-3:33 pm

1 stop5h 17m

Hilton Head Island

Wed 6/10

4:15 pm-11:27 pm

1 stop7h 12m

$271

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 6/13

12:10 pm-3:09 pm

Nonstop2h 59m

Hilton Head Island

Tue 6/16

2:43 pm-8:59 pm

1 stop6h 16m

$273

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Tue 5/12

6:00 am-2:11 pm

1 stop8h 11m

Hilton Head Island

Mon 5/18

3:08 pm-9:25 pm

1 stop6h 17m

$364

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Tue 5/12

6:05 am-3:41 pm

2 stops9h 36m

Hilton Head Island

Mon 5/18

3:08 pm-9:25 pm

1 stop6h 17m

$369

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 November, then you should wait until June to fly from Massachusetts, when ticket prices are also cheap, with an average price of $90.

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 from Massachusetts 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 $372 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 $223 on momondo.

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

No. A direct flight is the cheapest option for a flight between Massachusetts to Hilton Head Island.

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

$194

Fastest flight time

2h 45m

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 $194
The fastest flight from Massachusetts to Hilton Head Island takes 2h 45m
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

Frequently asked questions about flying from Massachusetts to Hilton Head Island

  • 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
7.1
2,980 reviews
Search JetBlue flights
DeltaPriceFrom $167Free CancellationRating
7.9
8,459 reviews
Search Delta flights
United AirlinesPriceFrom $183Free CancellationRating
7.4
9,691 reviews
Search United Airlines flights
American AirlinesPriceFrom $250Free CancellationRating
7.1
11,669 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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