$126 Find Cheap Flights from Hilton Head Island to Massachusetts

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hilton Head Island to Massachusetts departing on 5/23. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Massachusetts

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Massachusetts, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Massachusetts, as well as popular online travel agencies
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Flight Deals

Book Cheap Hilton Head Island to Massachusetts Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hilton Head Island to Massachusetts that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hilton Head Island to Massachusetts

Tue, Jun 23 - Thu, Jul 2
Delta Logo
4:15 pm - 11:27 pm
HHH
-
BOS
7h 12m
1 stop
Delta Logo
6:00 am - 11:31 am
BOS
-
HHH
5h 31m
1 stop
$237Delta
Wed, Jun 24 - Thu, Jul 2
American Airlines Logo
5:21 pm - 12:40 am
HHH
-
BOS
7h 19m
1 stop
American Airlines Logo
6:04 am - 11:10 am
BOS
-
HHH
5h 06m
1 stop
$257American Airlines
Thu, May 28 - Sat, May 30
American Airlines Logo
5:21 pm - 12:40 am
HHH
-
BOS
7h 19m
1 stop
American Airlines Logo
8:47 am - 11:46 am
BOS
-
HHH
2h 59mnonstop
$261American Airlines
Tue, May 12 - Tue, May 19
Delta Logo
4:16 pm - 10:25 pm
HHH
-
BOS
6h 09m
1 stop
Delta Logo
8:00 am - 3:33 pm
BOS
-
HHH
7h 33m
1 stop
$271Delta
Tue, Jun 23 - Tue, Jun 30
Delta Logo
4:15 pm - 11:27 pm
HHH
-
BOS
7h 12m
1 stop
Delta Logo
8:05 am - 3:32 pm
BOS
-
HHH
7h 27m
1 stop
$273Delta
Wed, May 13 - Wed, May 20
Delta Logo
12:18 pm - 10:25 pm
HHH
-
BOS
10h 07m
2 stops
Delta Logo
9:10 am - 3:33 pm
BOS
-
HHH
6h 23m
1 stop
$276Delta
Wed, Jun 17 - Mon, Jun 22
Delta Logo
4:15 pm - 11:27 pm
HHH
-
BOS
7h 12m
1 stop
Delta Logo
10:00 pm - 11:31 am
BOS
-
HHH
13h 31m
1 stop
$285Delta
Sat, May 23 - Sat, Jun 6
American Airlines Logo
12:16 pm - 2:54 pm
HHH
-
BOS
2h 38mnonstop
American Airlines Logo
12:10 pm - 3:09 pm
BOS
-
HHH
2h 59mnonstop
$289American Airlines
Tue, Aug 25 - Wed, Aug 26
United Airlines Logo
1:45 pm - 9:25 am
HHH
-
ACK
19h 40m
1 stop
United Airlines Logo
3:49 pm - 12:52 pm
ACK
-
HHH
21h 03m
1 stop
$942United Airlines
Tue, Aug 25 - Wed, Aug 26
United Airlines Logo
1:45 pm - 9:25 am
HHH
-
ACK
19h 40m
1 stop
United Airlines Logo
3:49 pm - 12:52 pm
ACK
-
HHH
21h 03m
1 stop
$952United Airlines
Booking Insights

KAYAK's insights & trends for Hilton Head Island to Massachusetts flights

Get data-powered insights and trends into flights from Hilton Head Island to Massachusetts to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Hilton Head Island to Massachusetts?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Hilton Head Island to Massachusetts departing in June.

What is the cheapest Hilton Head Island to Massachusetts flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Massachusetts from Hilton Head Island found in the last 72 hours was to Boston, at $291 round-trip. The most popular route is from Hilton Head Island (HHH) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $291.

Can I save money by flying with a layover from Hilton Head Island to Massachusetts?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $291, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$126
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly with an average 42% increase in price.
Flight from Hilton Head Island to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Hilton Head Island to Massachusetts?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hilton Head Island to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hilton Head Island to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Hilton Head Island to Massachusetts is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hilton Head Island to Massachusetts?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Hilton Head Island to Massachusetts with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hilton Head Island to Massachusetts?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Hilton Head Island to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between Hilton Head Island and Massachusetts per day?

    There is a maximum of 1 nonstop flight a day that takes off from Hilton Head Island and lands in Massachusetts, with an average flight time of 2h 38m. The most common departure time is 12:00 pm and most flights take off in the morning. Each week, there are 1 flights.

Reviews of the top airline flying from Hilton Head Island to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Hilton Head Island to Massachusetts. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hilton Head Island to Massachusetts? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11673 reviews
7.2Comfort
6.4Food
7.5Boarding
6.9Entertainment
7.9Crew
Airline reviews

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

10.0 ExcellentStan, Apr 2026
LAX - PHL
Read more American Airlines reviews

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

Flight was fine, but not having WiFi was a major negative

Everything you need to know for your flight from Hilton Head Island to Massachusetts

Information on your arrival and departure airports

Hilton Head Island (HHH)