$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 1/14. 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

Fri, Jan 16 - Mon, Jan 19
American Airlines Logo
12:51 pm - 6:19 pm
HHH
-
BOS
5h 28m1 stop
American Airlines Logo
8:03 pm - 12:20 pm
BOS
-
HHH
16h 17m2 stops
$266American Airlines
Fri, Jan 16 - Mon, Jan 19
American Airlines Logo
12:51 pm - 11:43 pm
HHH
-
BOS
10h 52m2 stops
American Airlines Logo
8:03 pm - 12:20 pm
BOS
-
HHH
16h 17m2 stops
$271American Airlines
Thu, Jan 8 - Thu, Jan 22
American Airlines Logo
12:51 pm - 6:19 pm
HHH
-
BOS
5h 28m1 stop
American Airlines Logo
6:43 am - 12:20 pm
BOS
-
HHH
5h 37m1 stop
$277American Airlines
Thu, Jan 8 - Thu, Jan 22
American Airlines Logo
12:51 pm - 8:11 pm
HHH
-
BOS
7h 20m2 stops
American Airlines Logo
6:43 am - 12:20 pm
BOS
-
HHH
5h 37m1 stop
$282American Airlines
Thu, Jan 8 - Thu, Jan 22
American Airlines Logo
12:51 pm - 8:30 pm
HHH
-
BOS
7h 39m2 stops
American Airlines Logo
7:00 am - 2:59 pm
BOS
-
HHH
7h 59m2 stops
$287American Airlines
Thu, Jan 1 - Wed, Jan 7
American Airlines Logo
6:13 pm - 10:37 pm
HHH
-
BOS
4h 24m1 stop
American Airlines Logo
6:43 am - 12:20 pm
BOS
-
HHH
5h 37m1 stop
$334American Airlines
Thu, Jan 1 - Tue, Jan 6
American Airlines Logo
6:13 pm - 10:37 pm
HHH
-
BOS
4h 24m1 stop
American Airlines Logo
6:00 am - 2:59 pm
BOS
-
HHH
8h 59m2 stops
$339American Airlines
Mon, Jan 5 - Tue, Jan 6
American Airlines Logo
6:13 pm - 10:37 pm
HHH
-
BOS
4h 24m1 stop
American Airlines Logo
8:30 am - 2:59 pm
BOS
-
HHH
6h 29m1 stop
$344American Airlines
Thu, Jan 1 - Fri, Jan 9
American Airlines Logo
6:13 pm - 10:37 pm
HHH
-
BOS
4h 24m1 stop
American Airlines Logo
6:43 am - 12:20 pm
BOS
-
HHH
5h 37m1 stop
$347American Airlines
Mon, Jan 5 - Tue, Jan 6
American Airlines Logo
6:13 pm - 10:37 pm
HHH
-
BOS
4h 24m1 stop
American Airlines Logo
6:00 am - 2:59 pm
BOS
-
HHH
8h 59m2 stops
$349American 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 January.

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.

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 seasonFebruary
Cheapest flight$126
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly with an average 33% 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 11049 reviews
7.2Comfort
6.5Food
7.5Boarding
6.9Entertainment
8.0Crew
Airline reviews

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

8.0 ExcellentAnonymous, Dec 2025
BNA - JFK
Read more American Airlines reviews

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

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

Information on your arrival and departure airports