$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 2/25. 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

Wed, Jun 3 - Sun, Jun 7
American Airlines Logo
5:54 pm - 12:34 am
HHH
-
BOS
6h 40m
1 stop
American Airlines Logo
10:11 am - 5:09 pm
BOS
-
HHH
6h 58m
1 stop
$388American Airlines
Wed, Jun 3 - Sun, Jun 7
American Airlines Logo
5:54 pm - 12:34 am
HHH
-
BOS
6h 40m
1 stop
American Airlines Logo
6:00 am - 2:18 pm
BOS
-
HHH
8h 18m
2 stops
$393American Airlines
Sat, Feb 7 - Wed, Feb 11
American Airlines Logo
12:54 pm - 6:15 pm
HHH
-
BOS
5h 21m
1 stop
American Airlines Logo
9:45 am - 2:59 pm
BOS
-
HHH
5h 14m
1 stop
$412American Airlines
Sat, Feb 7 - Wed, Feb 11
American Airlines Logo
12:54 pm - 10:19 pm
HHH
-
BOS
9h 25m
2 stops
American Airlines Logo
8:30 am - 2:59 pm
BOS
-
HHH
6h 29m
1 stop
$417American Airlines
Sat, Feb 7 - Wed, Feb 11
American Airlines Logo
3:29 pm - 10:19 pm
HHH
-
BOS
6h 50m
2 stops
American Airlines Logo
8:00 am - 2:59 pm
BOS
-
HHH
6h 59m
2 stops
$422American Airlines
Sat, Apr 4 - Sat, Apr 11
American Airlines Logo
2:58 pm - 9:49 pm
HHH
-
BOS
6h 51m
1 stop
American Airlines Logo
12:07 pm - 6:20 pm
BOS
-
HHH
6h 13m
1 stop
$429American Airlines
Wed, Jun 3 - Sun, Jun 7
Delta Logo
12:00 pm - 10:27 pm
HHH
-
BOS
10h 27m
2 stops
Delta Logo
6:00 am - 3:18 pm
BOS
-
HHH
9h 18m
2 stops
$439Delta
Sat, Feb 7 - Thu, Feb 12
American Airlines Logo
3:29 pm - 8:33 pm
HHH
-
BOS
5h 04m
1 stop
American Airlines Logo
9:00 am - 3:41 pm
BOS
-
HHH
6h 41m
1 stop
$443American Airlines
Sat, Feb 7 - Thu, Feb 12
American Airlines Logo
12:54 pm - 10:44 pm
HHH
-
BOS
9h 50m
2 stops
American Airlines Logo
9:00 am - 3:41 pm
BOS
-
HHH
6h 41m
1 stop
$448American Airlines
Sat, Jun 6 - Sat, Jun 13
American Airlines Logo
5:54 pm - 12:34 am
HHH
-
BOS
6h 40m
1 stop
American Airlines Logo
6:00 am - 11:10 am
BOS
-
HHH
5h 10m
1 stop
$459American 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.

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 $559 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 $559.

What is the cheapest month to fly from Hilton Head Island to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Hilton Head Island to Massachusetts, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Hilton Head Island to Massachusetts is April, when tickets cost $149 (return) on average. On the other hand, the most expensive months are February and June, when the average cost of round-trip tickets is $456 and $426 respectively.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$126
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly and prices are also 13% lower on average.
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.

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.
7.2
American AirlinesOverall score based on 11201 reviews
7.5Boarding
7.2Comfort
6.9Entertainment
8.0Crew
6.4Food
Airline reviews

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

4.0 OkayAllison, Jan 2026
MKE - DFW
Read more American Airlines reviews

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

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)