$106 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 11/27. 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, Dec 3 - Sun, Dec 7
American Airlines Logo
3:27 pm - 10:33 pmHHH-BOS
7h 06m1 stop
American Airlines Logo
7:30 am - 1:47 pmBOS-HHH
6h 17m1 stop
$217American Airlines
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Wed, Dec 3 - Sun, Dec 7
American Airlines Logo
3:27 pm - 10:16 pmHHH-BOS
6h 49m2 stops
American Airlines Logo
7:30 am - 1:47 pmBOS-HHH
6h 17m1 stop
$222American Airlines
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Wed, Dec 3 - Sun, Dec 7
American Airlines Logo
12:52 pm - 7:54 pmHHH-BOS
7h 02m2 stops
American Airlines Logo
6:00 am - 1:47 pmBOS-HHH
7h 47m2 stops
$227American Airlines
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Wed, Nov 12 - Sun, Nov 16
American Airlines Logo
7:07 pm - 12:16 amHHH-BOS
5h 09m1 stop
American Airlines Logo
5:25 am - 11:49 amBOS-HHH
6h 24m1 stop
$252American Airlines
Find Deal
Wed, Nov 12 - Sun, Nov 16
American Airlines Logo
3:27 pm - 10:47 pmHHH-BOS
7h 20m2 stops
American Airlines Logo
7:30 am - 2:19 pmBOS-HHH
6h 49m1 stop
$257American Airlines
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Wed, Nov 12 - Sun, Nov 16
American Airlines Logo
3:27 pm - 10:22 pmHHH-BOS
6h 55m2 stops
American Airlines Logo
6:00 am - 2:19 pmBOS-HHH
8h 19m2 stops
$262American Airlines
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Fri, Mar 27 - Tue, Mar 31
American Airlines Logo
4:19 pm - 10:44 pmHHH-BOS
6h 25m1 stop
American Airlines Logo
8:10 am - 3:59 pmBOS-HHH
7h 49m1 stop
$427American Airlines
Find Deal
Fri, Mar 27 - Tue, Mar 31
American Airlines Logo
4:19 pm - 10:44 pmHHH-BOS
6h 25m1 stop
American Airlines Logo
6:02 am - 2:19 pmBOS-HHH
8h 17m2 stops
$432American Airlines
Find Deal
Fri, Mar 27 - Tue, Mar 31
American Airlines Logo
4:19 pm - 10:44 pmHHH-BOS
6h 25m1 stop
American Airlines Logo
10:00 am - 3:59 pmBOS-HHH
5h 59m1 stop
$438American Airlines
Find Deal
Fri, Mar 27 - Tue, Mar 31
American Airlines Logo
4:19 pm - 10:44 pmHHH-BOS
6h 25m1 stop
American Airlines Logo
5:52 am - 2:19 pmBOS-HHH
8h 27m2 stops
$443American Airlines
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?

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’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.

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Good to know

Low seasonSeptember
Cheapest flight$106
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly and prices are also 17% 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.

  • 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 11030 reviews
6.4Food
8.0Crew
7.2Comfort
7.5Boarding
6.9Entertainment
Airline reviews

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

8.0 ExcellentKohMeng, Oct 2025DFW - LAX
Read more American Airlines reviews

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

The only thing to like was that we eventually got to our destination

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)

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