Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Massachusetts to Hilton Head Island from $161

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 9/6. 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
5:30 am - 10:37 amBDL  Hartford Bradley Intl-HHH Hilton Head Island
5h 07m1 stop Washington, D.C. Reagan-National
American Airlines Logo
2:56 pm - 9:35 pmHHH  Hilton Head Island-BDL Hartford Bradley Intl
6h 39m1 stop Charlotte Douglas
$313American Airlines
Sat, Oct 3 - Sat, Oct 10
American Airlines Logo
7:08 am - 1:37 pmBDL  Hartford Bradley Intl-HHH Hilton Head Island
6h 29m1 stop Charlotte Douglas
American Airlines Logo
6:13 pm - 11:29 pmHHH  Hilton Head Island-BDL Hartford Bradley Intl
5h 16m1 stop Charlotte Douglas
$313American Airlines
Tue, Oct 6 - Sat, Oct 10
United Airlines Logo
6:00 am - 2:13 pmBDL  Hartford Bradley Intl-HHH Hilton Head Island
8h 13m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
United Airlines Logo
3:00 pm - 9:37 pmHHH  Hilton Head Island-BDL Hartford Bradley Intl
6h 37m1 stop Chicago O'Hare Intl
$318United Airlines
Sat, Oct 3 - Sat, Oct 10
United Airlines Logo
6:00 am - 2:03 pmBDL  Hartford Bradley Intl-HHH Hilton Head Island
8h 03m1 stop Chicago O'Hare Intl
United Airlines Logo
2:48 pm - 11:08 pmHHH  Hilton Head Island-BDL Hartford Bradley Intl
8h 20m1 stop Chicago O'Hare Intl
$319United Airlines
Wed, Sep 2 - Sat, Sep 5
Delta Logo
9:05 am - 3:27 pmBOS  Boston Logan Intl-HHH Hilton Head Island
6h 22m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:17 pm - 10:26 pmHHH  Hilton Head Island-BOS Boston Logan Intl
6h 09m1 stop New York LaGuardia
$319Delta
Thu, Sep 10 - Mon, Sep 14
Delta Logo
7:00 am - 11:43 amBOS  Boston Logan Intl-HHH Hilton Head Island
4h 43m1 stop New York LaGuardia
Delta Logo
4:13 pm - 10:24 pmHHH  Hilton Head Island-BOS Boston Logan Intl
6h 11m1 stop New York LaGuardia
$319Delta
Sat, Oct 31 - Mon, Nov 2
American Airlines Logo
6:04 am - 10:27 amBOS  Boston Logan Intl-HHH Hilton Head Island
4h 23m1 stop Washington, D.C. Reagan-National
American Airlines Logo
5:15 pm - 10:24 pmHHH  Hilton Head Island-BOS Boston Logan Intl
5h 09m1 stop Charlotte Douglas
$319American Airlines
Mon, Sep 7 - Thu, Sep 17
American Airlines Logo
6:00 am - 11:05 amBOS  Boston Logan Intl-HHH Hilton Head Island
5h 05m1 stop Charlotte Douglas
American Airlines Logo
12:29 pm - 5:56 pmHHH  Hilton Head Island-BOS Boston Logan Intl
5h 27m1 stop Charlotte Douglas
$319American Airlines
Wed, Oct 7 - Tue, Oct 13
United Airlines Logo
6:00 am - 2:03 pmBOS  Boston Logan Intl-HHH Hilton Head Island
8h 03m1 stop Chicago O'Hare Intl
United Airlines Logo
2:48 pm - 9:59 pmHHH  Hilton Head Island-BOS Boston Logan Intl
7h 11m1 stop Chicago O'Hare Intl
$319United Airlines
Thu, Sep 10 - Wed, Sep 16
Delta Logo
7:00 am - 11:43 amBOS  Boston Logan Intl-HHH Hilton Head Island
4h 43m1 stop New York LaGuardia
Delta Logo
4:13 pm - 10:24 pmHHH  Hilton Head Island-BOS Boston Logan Intl
6h 11m1 stop New York LaGuardia
$319Delta
Sat, Oct 17 - Fri, Oct 23

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

American Airlines flights from Massachusetts to Hilton Head Island

Our best American Airlines deals on Massachusetts to Hilton Head Island flight tickets
American Airlines
Oct 3
BDL5:30 amHartford Bradley Intl
5h 07m
1 stop
HHH10:37 amHilton Head Island
Oct 10
HHH2:56 pmHilton Head Island
6h 39m
1 stop
BDL9:35 pmHartford Bradley Intl
$313
American Airlines
Sep 18
BOS6:00 amBoston Logan Intl
4h 37m
1 stop
HHH10:37 amHilton Head Island
Sep 25
HHH5:15 pmHilton Head Island
5h 09m
1 stop
BOS10:24 pmBoston Logan Intl
$320
American Airlines
Aug 14
BOS6:00 amBoston Logan Intl
4h 27m
1 stop
HHH10:27 amHilton Head Island
Aug 21
HHH3:27 pmHilton Head Island
4h 39m
1 stop
BOS8:06 pmBoston Logan Intl
$321

Delta flights from Massachusetts to Hilton Head Island

Our best Delta deals on Massachusetts to Hilton Head Island flight tickets
Delta
Sep 10
BOS9:05 amBoston Logan Intl
6h 22m
1 stop
HHH3:27 pmHilton Head Island
Sep 14
HHH4:17 pmHilton Head Island
6h 09m
1 stop
BOS10:26 pmBoston Logan Intl
$319
Delta
Sep 10
BOS6:05 amBoston Logan Intl
9h 22m
2 stops
HHH3:27 pmHilton Head Island
Sep 14
HHH4:17 pmHilton Head Island
6h 09m
1 stop
BOS10:26 pmBoston Logan Intl
$324
Delta
Aug 31
BOS7:00 amBoston Logan Intl
8h 32m
2 stops
HHH3:32 pmHilton Head Island
Oct 2
HHH12:17 pmHilton Head Island
10h 27m
2 stops
BOS10:44 pmBoston Logan Intl
$329

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 August 9, 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

HartfordHilton Head Island

BDL Hartford Bradley Intl - HHH Hilton Head Island

BDLHHH

Hartford Bradley Intl

Sat 10/3

5:30 am-10:37 am

1 stop5h 07m

Hilton Head Island

Sat 10/10

2:56 pm-9:35 pm

1 stop6h 39m

$313

HartfordHilton Head Island

BDL Hartford Bradley Intl - HHH Hilton Head Island

BDLHHH

Hartford Bradley Intl

Tue 10/6

7:08 am-1:37 pm

1 stop6h 29m

Hilton Head Island

Sat 10/10

6:13 pm-11:29 pm

1 stop5h 16m

$313

HartfordHilton Head Island

BDL Hartford Bradley Intl - HHH Hilton Head Island

BDLHHH

Hartford Bradley Intl

Sat 10/3

6:00 am-2:13 pm

2 stops8h 13m

Hilton Head Island

Sat 10/10

3:00 pm-9:37 pm

1 stop6h 37m

$318

HartfordHilton Head Island

BDL Hartford Bradley Intl - HHH Hilton Head Island

BDLHHH

Hartford Bradley Intl

Wed 9/2

6:00 am-2:03 pm

1 stop8h 03m

Hilton Head Island

Sat 9/5

2:48 pm-11:08 pm

1 stop8h 20m

$319

BostonHilton Head Island

BOS Boston Logan Intl - HHH Hilton Head Island

BOSHHH

Boston Logan Intl

Thu 9/10

9:05 am-3:27 pm

1 stop6h 22m

Hilton Head Island

Mon 9/14

4:17 pm-10:26 pm

1 stop6h 09m

$319

BostonHilton Head Island

BOS Boston Logan Intl - HHH Hilton Head Island

BOSHHH

Boston Logan Intl

Sat 10/31

7:00 am-11:43 am

1 stop4h 43m

Hilton Head Island

Mon 11/2

4:13 pm-10:24 pm

1 stop6h 11m

$319
Quickest round-trip

BostonHilton Head Island

BOS Boston Logan Intl - HHH Hilton Head Island

BOSHHH

Boston Logan Intl

Mon 9/7

6:04 am-10:27 am

1 stop4h 23m

Hilton Head Island

Thu 9/17

5:15 pm-10:24 pm

1 stop5h 09m

$319

BostonHilton Head Island

BOS Boston Logan Intl - HHH Hilton Head Island

BOSHHH

Boston Logan Intl

Wed 10/7

6:00 am-11:05 am

1 stop5h 05m

Hilton Head Island

Tue 10/13

12:29 pm-5:56 pm

1 stop5h 27m

$319

BostonHilton Head Island

BOS Boston Logan Intl - HHH Hilton Head Island

BOSHHH

Boston Logan Intl

Thu 9/10

6:00 am-2:03 pm

1 stop8h 03m

Hilton Head Island

Wed 9/16

2:48 pm-9:59 pm

1 stop7h 11m

$319

BostonHilton Head Island

BOS Boston Logan Intl - HHH Hilton Head Island

BOSHHH

Boston Logan Intl

Sat 10/17

7:00 am-11:43 am

1 stop4h 43m

Hilton Head Island

Fri 10/23

4:13 pm-10:24 pm

1 stop6h 11m

$319

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 June to fly from Massachusetts, when ticket prices are also cheap, with an average price of $314.

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 $398 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 $359 on momondo.

What cabin class options are available on Massachusetts to Hilton Head Island flights?

There are 2 cabin classes 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

Fastest flight time

2h 51m

Direct flights

Sun

Airports in Hilton Head Island

1 airport
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
8,499 reviews
Search Delta flights
United AirlinesPriceFrom $183Free CancellationRating
7.4
10,089 reviews
Search United Airlines flights
JetBluePriceFrom $212Free CancellationRating
7.1
3,030 reviews
Search JetBlue flights
American AirlinesPriceFrom $251Free CancellationRating
7.1
11,892 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 9/8
Tue 9/15
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States