$109 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 8/30. 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

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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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Cheap Flights from Hilton Head Island to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$234
Boston
Bostonnonstop$234

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

Sat, Aug 30 - Wed, Sep 3
American Airlines Logo
3:41 pm - 6:16 pmHHH-BOS
2h 35mnonstop
American Airlines Logo
7:45 am - 12:17 pmBOS-HHH
4h 32m1 stop
$234American Airlines
Find Deal
Wed, Aug 20 - Sat, Aug 23
American Airlines Logo
11:19 am - 4:38 pmHHH-BOS
5h 19m1 stop
American Airlines Logo
12:25 pm - 3:11 pmBOS-HHH
2h 46mnonstop
$241American Airlines
Find Deal
Sat, Aug 30 - Tue, Sep 2
American Airlines Logo
3:41 pm - 6:16 pmHHH-BOS
2h 35mnonstop
American Airlines Logo
7:28 am - 3:05 pmBOS-HHH
7h 37m2 stops
$244American Airlines
Find Deal
Wed, Aug 20 - Sat, Aug 23
American Airlines Logo
12:29 pm - 9:53 pmHHH-BOS
9h 24m2 stops
American Airlines Logo
12:25 pm - 3:11 pmBOS-HHH
2h 46mnonstop
$251American Airlines
Find Deal
Fri, Aug 29 - Tue, Sep 2
American Airlines Logo
1:15 pm - 6:54 pmHHH-BOS
5h 39m1 stop
American Airlines Logo
6:00 am - 10:49 amBOS-HHH
4h 49m1 stop
$274American Airlines
Find Deal
Sat, Aug 30 - Wed, Sep 3
Delta Logo
12:11 pm - 11:21 pmHHH-BOS
11h 10m2 stops
Delta Logo
8:30 am - 3:22 pmBOS-HHH
6h 52m1 stop
$319Delta
Find Deal
Sat, Aug 30 - Wed, Sep 3
Delta Logo
12:11 pm - 11:21 pmHHH-BOS
11h 10m2 stops
Delta Logo
6:00 am - 3:22 pmBOS-HHH
9h 22m2 stops
$324Delta
Find Deal
Mon, Sep 22 - Wed, Sep 24
United Airlines Logo
12:06 pm - 4:28 pmHHH-BOS
4h 22m1 stop
United Airlines Logo
6:00 am - 11:25 amBOS-HHH
5h 25m1 stop
$339United Airlines
Find Deal
Mon, Sep 22 - Wed, Sep 24
United Airlines Logo
12:06 pm - 6:55 pmHHH-BOS
6h 49m2 stops
United Airlines Logo
6:00 am - 11:25 amBOS-HHH
5h 25m1 stop
$439United Airlines
Find Deal
Mon, Sep 8 - Fri, Sep 12
 Logo
12:06 pm - 9:55 amHHH-ACK
21h 49m1 stop
 Logo
10:05 am - 11:25 amACK-HHH
25h 20m2 stops
$1,070
Find Deal
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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Hilton Head Island to Massachusetts.

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 September, when tickets cost $217 (return) on average. On the other hand, the most expensive months are March and October, when the average cost of round-trip tickets is $496 and $468 respectively.

What’s the cheapest day of the week to fly from Hilton Head Island to Massachusetts?

The average price of all round-trip flights from Hilton Head Island to Massachusetts clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Hilton Head Island to Massachusetts, look for departures on Thursdays and avoid leaving on a Tuesday, as it's usually the priciest day. When flying back from Massachusetts, Saturday is the cheapest day to fly and Thursday is the most expensive.


Good to know

Low seasonJanuary
Cheapest flight$109
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 15% 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.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally in the morning, when round-trip flights cost $506 on average. The most expensive time of day to fly to Massachusetts is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $523.

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 10000 reviews
6.5Food
6.9Entertainment
7.2Comfort
7.5Boarding
8.0Crew
Airline reviews

Very poor delay in dfw was really bad n long

2.0 Mediocredavix, Jul 2025DFW - MKE
Read more American Airlines reviews

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

Delayed flight, so I switched fights to SFO to Phoenix , Phoenix to DSM. Excellent service through American Airlines

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

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