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Cheap flights from Massachusetts to Hilton Head Island from $188

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 9/8. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
11:30 am - 2:15 pm
BOS
-
HHH
2h 45mnonstop
American Airlines Logo
2:45 pm - 5:21 pm
HHH
-
BOS
2h 36mnonstop
$289American Airlines
Sat, Jul 18 - Sat, Jul 25
American Airlines Logo
8:05 am - 2:16 pm
BOS
-
HHH
6h 11m
1 stop
American Airlines Logo
2:45 pm - 5:21 pm
HHH
-
BOS
2h 36mnonstop
$299American Airlines
Tue, Jul 21 - Sat, Jul 25
American Airlines Logo
11:41 am - 2:26 pm
BOS
-
HHH
2h 45mnonstop
American Airlines Logo
11:47 am - 6:04 pm
HHH
-
BOS
6h 17m
1 stop
$300American Airlines
Sat, Jul 4 - Wed, Jul 15
Delta Logo
10:00 am - 3:32 pm
BDL
-
HHH
5h 32m
1 stop
Delta Logo
12:15 pm - 6:05 pm
HHH
-
BDL
5h 50m
1 stop
$303Delta
Sat, Aug 29 - Tue, Sep 1
Delta Logo
8:00 am - 3:32 pm
BDL
-
HHH
7h 32m
1 stop
Delta Logo
12:15 pm - 11:51 pm
HHH
-
BDL
11h 36m
2 stops
$308Delta
Sat, Aug 29 - Tue, Sep 1
United Airlines Logo
6:00 am - 2:03 pm
BDL
-
HHH
8h 03m
1 stop
United Airlines Logo
2:48 pm - 9:38 pm
HHH
-
BDL
6h 50m
1 stop
$309United Airlines
Thu, Aug 20 - Wed, Aug 26
American Airlines Logo
6:00 am - 10:37 am
BOS
-
HHH
4h 37m
1 stop
American Airlines Logo
3:27 pm - 10:13 pm
HHH
-
BOS
6h 46m
1 stop
$309American Airlines
Wed, Jul 29 - Wed, Aug 5
Delta Logo
5:30 am - 3:32 pm
BDL
-
HHH
10h 02m
2 stops
Delta Logo
12:15 pm - 11:51 pm
HHH
-
BDL
11h 36m
2 stops
$313Delta
Sat, Aug 29 - Tue, Sep 1
United Airlines Logo
6:00 am - 2:03 pm
BDL
-
HHH
8h 03m
2 stops
United Airlines Logo
2:48 pm - 9:38 pm
HHH
-
BDL
6h 50m
1 stop
$314United Airlines
Thu, Aug 20 - Wed, Aug 26
United Airlines Logo
6:00 am - 2:03 pm
BDL
-
HHH
8h 03m
1 stop
United Airlines Logo
2:48 pm - 9:38 pm
HHH
-
BDL
6h 50m
1 stop
$386United Airlines
Sat, Aug 29 - Tue, Sep 1

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American Airlines flights from Massachusetts to Hilton Head Island

Our best American Airlines deals on Massachusetts to Hilton Head Island flight tickets
American Airlines
Jul 18
BOS11:30 amBoston Logan Intl
2h 45m
HHH2:15 pmHilton Head Island
Jul 25
HHH2:45 pmHilton Head Island
2h 36m
BOS5:21 pmBoston Logan Intl
$289
American Airlines
Jul 21
BOS8:05 amBoston Logan Intl
6h 11m
1 stop
HHH2:16 pmHilton Head Island
Jul 25
HHH2:45 pmHilton Head Island
2h 36m
BOS5:21 pmBoston Logan Intl
$299
American Airlines
Jul 4
BOS11:41 amBoston Logan Intl
2h 45m
HHH2:26 pmHilton Head Island
Jul 15
HHH11:47 amHilton Head Island
6h 17m
1 stop
BOS6:04 pmBoston Logan Intl
$300

United Airlines flights from Massachusetts to Hilton Head Island

Our best United Airlines deals on Massachusetts to Hilton Head Island flight tickets
United Airlines
Aug 20
BDL6:00 amHartford Bradley Intl
8h 03m
1 stop
HHH2:03 pmHilton Head Island
Aug 26
HHH2:48 pmHilton Head Island
6h 50m
1 stop
BDL9:38 pmHartford Bradley Intl
$309
United Airlines
Aug 20
BDL6:00 amHartford Bradley Intl
8h 03m
2 stops
HHH2:03 pmHilton Head Island
Aug 26
HHH2:48 pmHilton Head Island
6h 50m
1 stop
BDL9:38 pmHartford Bradley Intl
$314
United Airlines
Aug 6
BOS5:45 amBoston Logan Intl
8h 36m
2 stops
HHH2:21 pmHilton Head Island
Aug 11
HHH2:48 pmHilton Head Island
8h 46m
1 stop
BOS11:34 pmBoston Logan Intl
$342

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 June 17, 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

Sat 7/18

11:30 am-2:15 pm

Nonstop2h 45m

Hilton Head Island

Sat 7/25

2:45 pm-5:21 pm

Nonstop2h 36m

$289

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Tue 7/21

8:05 am-2:16 pm

1 stop6h 11m

Hilton Head Island

Sat 7/25

2:45 pm-5:21 pm

Nonstop2h 36m

$299

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 7/4

11:41 am-2:26 pm

Nonstop2h 45m

Hilton Head Island

Wed 7/15

11:47 am-6:04 pm

1 stop6h 17m

$300

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sat 8/29

10:00 am-3:32 pm

1 stop5h 32m

Hilton Head Island

Tue 9/1

12:15 pm-6:05 pm

1 stop5h 50m

$303

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sat 8/29

8:00 am-3:32 pm

1 stop7h 32m

Hilton Head Island

Tue 9/1

12:15 pm-11:51 pm

2 stops11h 36m

$308

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Thu 8/20

6:00 am-2:03 pm

1 stop8h 03m

Hilton Head Island

Wed 8/26

2:48 pm-9:38 pm

1 stop6h 50m

$309

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Wed 7/29

6:00 am-10:37 am

1 stop4h 37m

Hilton Head Island

Wed 8/5

3:27 pm-10:13 pm

1 stop6h 46m

$309

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sat 8/29

5:30 am-3:32 pm

2 stops10h 02m

Hilton Head Island

Tue 9/1

12:15 pm-11:51 pm

2 stops11h 36m

$313

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Thu 8/20

6:00 am-2:03 pm

2 stops8h 03m

Hilton Head Island

Wed 8/26

2:48 pm-9:38 pm

1 stop6h 50m

$314

HartfordHilton Head Island

BDL - HHH

BDLHHH

Hartford Bradley Intl

Sat 8/29

6:00 am-2:03 pm

1 stop8h 03m

Hilton Head Island

Tue 9/1

2:48 pm-9:38 pm

1 stop6h 50m

$386

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 April, then you should wait until August to fly from Massachusetts, when ticket prices are also cheap, with an average price of $168.

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 $380 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?

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

$299

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 $299
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

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
DeltaPriceFrom $148Free CancellationRating
7.8
8,406 reviews
Search Delta flights
United AirlinesPriceFrom $183Free CancellationRating
7.4
9,845 reviews
Search United Airlines flights
American AirlinesPriceFrom $250Free CancellationRating
7.1
11,670 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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