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Cheap flights from Massachusetts to Hilton Head Island from $104

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 1/17. 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
9:45 am - 2:59 pmBOS-HHH
5h 14m1 stop
American Airlines Logo
4:15 pm - 10:19 pmHHH-BOS
6h 04m1 stop
$222American Airlines
Find Deal
Mon, Feb 9 - Sun, Feb 15
American Airlines Logo
7:00 am - 2:59 pmBOS-HHH
7h 59m2 stops
American Airlines Logo
11:03 am - 6:06 pmHHH-BOS
7h 03m1 stop
$227American Airlines
Find Deal
Mon, Feb 9 - Sun, Feb 15
American Airlines Logo
6:00 am - 10:59 amBOS-HHH
4h 59m1 stop
American Airlines Logo
3:27 pm - 10:27 pmHHH-BOS
7h 00m2 stops
$232American Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
American Airlines Logo
8:30 am - 2:59 pmBOS-HHH
6h 29m1 stop
American Airlines Logo
12:51 pm - 10:19 pmHHH-BOS
9h 28m2 stops
$237American Airlines
Find Deal
Sat, Jan 10 - Tue, Jan 13
American Airlines Logo
6:00 am - 2:59 pmBOS-HHH
8h 59m2 stops
American Airlines Logo
12:51 pm - 8:30 pmHHH-BOS
7h 39m2 stops
$242American Airlines
Find Deal
Sat, Jan 10 - Tue, Jan 13
American Airlines Logo
7:24 am - 2:57 pmBOS-HHH
7h 33m2 stops
American Airlines Logo
3:27 pm - 10:16 pmHHH-BOS
6h 49m2 stops
$262American Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
American Airlines Logo
8:10 am - 3:44 pmBOS-HHH
7h 34m1 stop
American Airlines Logo
4:14 pm - 10:19 pmHHH-BOS
6h 05m1 stop
$264American Airlines
Find Deal
Thu, Feb 26 - Sat, Feb 28
American Airlines Logo
6:00 am - 2:59 pmBOS-HHH
8h 59m2 stops
American Airlines Logo
11:03 am - 6:04 pmHHH-BOS
7h 01m2 stops
$267American Airlines
Find Deal
Mon, Feb 9 - Sun, Feb 15
American Airlines Logo
12:19 pm - 5:52 pmBOS-HHH
5h 33m1 stop
American Airlines Logo
4:14 pm - 10:19 pmHHH-BOS
6h 05m1 stop
$277American Airlines
Find Deal
Mon, Feb 23 - Fri, Feb 27
American Airlines Logo
6:00 am - 2:28 pmBOS-HHH
8h 28m2 stops
American Airlines Logo
4:14 pm - 10:19 pmHHH-BOS
6h 05m1 stop
$282American Airlines
Find Deal
Mon, Feb 23 - Fri, Feb 27

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 9
BOS9:45 amBoston Logan Intl
5h 14m
1 stop
HHH2:59 pmHilton Head Island
Feb 15
HHH4:15 pmHilton Head Island
6h 04m
1 stop
BOS10:19 pmBoston Logan Intl
$222
Find similar
American Airlines
Feb 9
BOS7:00 amBoston Logan Intl
7h 59m
2 stops
HHH2:59 pmHilton Head Island
Feb 15
HHH11:03 amHilton Head Island
7h 03m
1 stop
BOS6:06 pmBoston Logan Intl
$227
Find similar
American Airlines
Dec 12
BOS6:00 amBoston Logan Intl
4h 59m
1 stop
HHH10:59 amHilton Head Island
Dec 15
HHH3:27 pmHilton Head Island
7h 00m
2 stops
BOS10:27 pmBoston Logan Intl
$232
Find similar

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 18
BOS8:30 amBoston Logan Intl
6h 42m
1 stop
HHH3:12 pmHilton Head Island
Apr 23
HHH4:00 pmHilton Head Island
5h 48m
1 stop
BOS9:48 pmBoston Logan Intl
$497
Find similar
United Airlines
May 15
BDL5:04 pmHartford Bradley Intl
20h 57m
1 stop
HHH2:01 pmHilton Head Island
May 22
HHH3:00 pmHilton Head Island
19h 25m
1 stop
BDL10:25 amHartford Bradley Intl
$830
Find similar
United Airlines
Mar 31
BDL6:00 amHartford Bradley Intl
9h 12m
3 stops
HHH3:12 pmHilton Head Island
Apr 1
HHH4:00 pmHilton Head Island
7h 50m
2 stops
BDL11:50 pmHartford Bradley Intl
$937
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 November 19, 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

Mon 2/9

9:45 am-2:59 pm

1 stop5h 14m

Hilton Head Island

Sun 2/15

4:15 pm-10:19 pm

1 stop6h 04m

$222

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

7:00 am-2:59 pm

2 stops7h 59m

Hilton Head Island

Sun 2/15

11:03 am-6:06 pm

1 stop7h 03m

$227

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 12/12

6:00 am-10:59 am

1 stop4h 59m

Hilton Head Island

Mon 12/15

3:27 pm-10:27 pm

2 stops7h 00m

$232

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 1/10

8:30 am-2:59 pm

1 stop6h 29m

Hilton Head Island

Tue 1/13

12:51 pm-10:19 pm

2 stops9h 28m

$237

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Sat 1/10

6:00 am-2:59 pm

2 stops8h 59m

Hilton Head Island

Tue 1/13

12:51 pm-8:30 pm

2 stops7h 39m

$242

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Fri 12/12

7:24 am-2:57 pm

2 stops7h 33m

Hilton Head Island

Mon 12/15

3:27 pm-10:16 pm

2 stops6h 49m

$262

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Thu 2/26

8:10 am-3:44 pm

1 stop7h 34m

Hilton Head Island

Sat 2/28

4:14 pm-10:19 pm

1 stop6h 05m

$264

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/9

6:00 am-2:59 pm

2 stops8h 59m

Hilton Head Island

Sun 2/15

11:03 am-6:04 pm

2 stops7h 01m

$267

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/23

12:19 pm-5:52 pm

1 stop5h 33m

Hilton Head Island

Fri 2/27

4:14 pm-10:19 pm

1 stop6h 05m

$277

BostonHilton Head Island

BOS - HHH

BOSHHH

Boston Logan Intl

Mon 2/23

6:00 am-2:28 pm

2 stops8h 28m

Hilton Head Island

Fri 2/27

4:14 pm-10:19 pm

1 stop6h 05m

$282

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 January to fly from Massachusetts, when ticket prices are also cheap, with an average price of $280.

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 $315. 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 $355 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 23% 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

Direct flights

None
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
2,903 reviews
Search JetBlue flights
DeltaPriceFrom $167Free CancellationRating
7.9
8,004 reviews
Search Delta flights
American AirlinesPriceFrom $255Free CancellationRating
7.2
11,046 reviews
Search American Airlines flights
United AirlinesPriceFrom $302Free CancellationRating
7.4
9,025 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

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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