$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 10/15. 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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Flight Deals

Cheap Flights from Hilton Head Island to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$283
Boston
Boston1 stop$283

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, Sep 30 - Sat, Oct 4
American Airlines Logo
12:56 pm - 5:39 pmHHH-BOS
4h 43m1 stop
American Airlines Logo
2:16 pm - 6:54 pmBOS-HHH
4h 38m1 stop
$283American Airlines
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Tue, Sep 30 - Sat, Oct 4
American Airlines Logo
3:26 pm - 10:50 pmHHH-BOS
7h 24m2 stops
American Airlines Logo
2:16 pm - 6:54 pmBOS-HHH
4h 38m1 stop
$288American Airlines
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Mon, Sep 29 - Fri, Oct 3
American Airlines Logo
5:20 pm - 11:44 pmHHH-BOS
6h 24m1 stop
American Airlines Logo
7:28 am - 4:47 pmBOS-HHH
9h 19m2 stops
$312American Airlines
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Mon, Sep 29 - Fri, Oct 3
American Airlines Logo
12:56 pm - 9:46 pmHHH-BOS
8h 50m2 stops
American Airlines Logo
7:28 am - 4:47 pmBOS-HHH
9h 19m2 stops
$317American Airlines
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Wed, Oct 8 - Sun, Oct 12
United Airlines Logo
11:57 am - 4:22 pmHHH-BOS
4h 25m1 stop
United Airlines Logo
6:00 am - 11:20 amBOS-HHH
5h 20m1 stop
$319United Airlines
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Tue, Sep 30 - Sat, Oct 4
American Airlines Logo
12:56 pm - 10:09 pmHHH-BOS
9h 13m2 stops
American Airlines Logo
7:28 am - 4:47 pmBOS-HHH
9h 19m2 stops
$359American Airlines
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Wed, Oct 8 - Sun, Oct 12
United Airlines Logo
11:57 am - 6:56 pmHHH-BOS
6h 59m2 stops
United Airlines Logo
6:00 am - 11:20 amBOS-HHH
5h 20m1 stop
$463United Airlines
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Mon, Sep 29 - Fri, Oct 3
Delta Logo
4:05 pm - 8:25 pmHHH-BOS
4h 20m1 stop
Delta Logo
8:05 am - 3:25 pmBOS-HHH
7h 20m1 stop
$487Delta
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Tue, Sep 30 - Sat, Oct 4
Delta Logo
12:14 pm - 6:31 pmHHH-BOS
6h 17m1 stop
Delta Logo
9:05 am - 3:25 pmBOS-HHH
6h 20m1 stop
$539Delta
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Mon, Sep 29 - Mon, Oct 6
United Airlines Logo
11:57 am - 4:22 pmHHH-BOS
4h 25m1 stop
United Airlines Logo
6:00 am - 11:16 amBOS-HHH
5h 16m1 stop
$799United Airlines
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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 September, when tickets cost $217 (return) on average. On the other hand, the most expensive months are October and November, when the average cost of round-trip tickets is $603 and $458 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.

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Good to know

Low seasonJanuary
Cheapest flight$126
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 24% 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
7.5Boarding
8.0Crew
6.9Entertainment
6.4Food
7.2Comfort
Airline reviews

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

10.0 ExcellentDouglas, Sep 2025SLC - CLT
Read more American Airlines reviews

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

The seat was so hard my tailbone was aching The crew was kind of a b**** because I made a joke that I didn't care if they close the door I total c*** when she was trying to f****** act like she was mad at me because I said that The flight was bumpy. Sure you didnt have control over that.

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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