$179 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 5/12. 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

Thu, Jul 16 - Sun, Jul 19
United Airlines Logo
3:05 pm - 11:16 pm
HHH
-
BOS
8h 11m
1 stop
United Airlines Logo
6:00 am - 12:52 pm
BOS
-
HHH
6h 52m
1 stop
$309United Airlines
Wed, Jun 3 - Wed, Jun 10
United Airlines Logo
3:05 pm - 11:16 pm
HHH
-
BOS
8h 11m
1 stop
United Airlines Logo
6:00 am - 12:52 pm
BOS
-
HHH
6h 52m
1 stop
$329United Airlines
Wed, Apr 29 - Wed, May 6
American Airlines Logo
6:39 pm - 11:07 pm
HHH
-
BOS
4h 28m
1 stop
American Airlines Logo
7:47 am - 12:37 pm
BOS
-
HHH
4h 50m
1 stop
$356American Airlines
Wed, Apr 29 - Wed, May 6
American Airlines Logo
11:03 am - 3:34 pm
HHH
-
BOS
4h 31m
1 stop
American Airlines Logo
8:07 am - 2:26 pm
BOS
-
HHH
6h 19m
2 stops
$362American Airlines
Thu, Jun 4 - Tue, Jun 9
United Airlines Logo
3:05 pm - 11:16 pm
HHH
-
BOS
8h 11m
1 stop
United Airlines Logo
6:00 am - 2:21 pm
BOS
-
HHH
8h 21m
1 stop
$379United Airlines
Tue, May 19 - Sun, May 24
Delta Logo
4:16 pm - 10:25 pm
HHH
-
BOS
6h 09m
1 stop
Delta Logo
6:30 pm - 11:37 am
BOS
-
HHH
17h 07m
1 stop
$384Delta
Wed, Apr 29 - Wed, May 6
Delta Logo
12:08 pm - 10:26 pm
HHH
-
BOS
10h 18m
2 stops
Delta Logo
6:00 am - 3:20 pm
BOS
-
HHH
9h 20m
2 stops
$387Delta
Sat, May 16 - Tue, May 26
Delta Logo
4:16 pm - 8:21 am
HHH
-
BOS
16h 05m
1 stop
Delta Logo
9:00 pm - 11:37 am
BOS
-
HHH
14h 37m
1 stop
$391Delta
Mon, Jul 20 - Fri, Jul 24
American Airlines Logo
10:55 am - 4:21 pm
HHH
-
ACK
5h 26m
1 stop
American Airlines Logo
4:51 pm - 4:00 pm
ACK
-
HHH
23h 09m
1 stop
$431American Airlines
Mon, Jul 20 - Fri, Jul 24
American Airlines Logo
10:55 am - 4:21 pm
HHH
-
ACK
5h 26m
1 stop
American Airlines Logo
4:51 pm - 11:05 am
ACK
-
HHH
18h 14m
2 stops
$462American 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.

Find deals

Good to know

Low seasonApril
Cheapest flight$179
Best time to beat the crowds with an average 52% drop in price.
Most popular time to fly with an average 62% 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.

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.
7.1
American AirlinesOverall score based on 11466 reviews
7.5Boarding
7.2Comfort
6.9Entertainment
6.4Food
7.9Crew
Airline reviews

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

2.0 Mediocresteven, Mar 2026
MIA - CLE
Read more American Airlines reviews

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

American Airlines did everything they could with the high Spring Break crowd. I was frustrated to be changed from 1st class to a middle seat at the back of the plane. This has happened before, not sure booking 1st class and paying the extra actually works.

I booked 1st class, my flights were changed and I was sitting in the middle at the back of the plane. A far cry from the 1st class I purchased for my flights. I am grateful I arrived on time.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Our flight was delayed 3 times and this is why I am giving such low reviews. Everything else was okay but being in the airport at 4:30pm for my initial flight at 7pm to not leave until after 9:30pm is insane,

Flights were constantly delayed. CRW took 50 minutes to get bags

Flight has been delayed every time I've ever taken it. Seats uncomfortable. Children behind me yelling the entire flight. Some of this is out of their control but overall just consistently not a great experience.

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

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)