$188 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 9/15. 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, 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

Sat, Jul 4 - Fri, Jul 10
American Airlines Logo
2:56 pm - 5:32 pm
HHH
-
BOS
2h 36mnonstop
American Airlines Logo
6:00 am - 10:37 am
BOS
-
HHH
4h 37m
1 stop
$299American Airlines
Sat, Jul 4 - Fri, Jul 10
American Airlines Logo
2:56 pm - 5:32 pm
HHH
-
BOS
2h 36mnonstop
American Airlines Logo
6:05 am - 11:17 am
BOS
-
HHH
5h 12m
1 stop
$300American Airlines
Sat, Jul 4 - Fri, Jul 10
American Airlines Logo
2:56 pm - 5:32 pm
HHH
-
BOS
2h 36mnonstop
American Airlines Logo
6:00 am - 10:37 am
BOS
-
HHH
4h 37m
1 stop
$301American Airlines
Tue, Jul 14 - Tue, Jul 21
American Airlines Logo
2:48 pm - 8:59 pm
HHH
-
BOS
6h 11m
1 stop
American Airlines Logo
10:13 am - 4:25 pm
BOS
-
HHH
6h 12m
1 stop
$309American Airlines
Tue, Jul 14 - Tue, Jul 21
Delta Logo
4:14 pm - 10:33 pm
HHH
-
BOS
6h 19m
1 stop
Delta Logo
7:00 am - 3:29 pm
BOS
-
HHH
8h 29m
2 stops
$314Delta
Tue, Jul 14 - Tue, Jul 21
Delta Logo
12:11 pm - 8:00 pm
HHH
-
BOS
7h 49m
2 stops
Delta Logo
6:00 am - 3:29 pm
BOS
-
HHH
9h 29m
2 stops
$319Delta
Tue, Jul 28 - Tue, Aug 4
Delta Logo
12:11 pm - 9:39 pm
HHH
-
BOS
9h 28m
2 stops
Delta Logo
6:05 am - 3:32 pm
BOS
-
HHH
9h 27m
2 stops
$334Delta
Mon, Jun 29 - Fri, Jul 3
United Airlines Logo
1:45 pm - 10:15 am
HHH
-
ACK
20h 30m
1 stop
United Airlines Logo
10:53 am - 1:02 pm
ACK
-
HHH
26h 09m
1 stop
$808United Airlines
Mon, Jun 29 - Fri, Jul 3
United Airlines Logo
1:45 pm - 10:15 am
HHH
-
ACK
20h 30m
1 stop
United Airlines Logo
3:44 pm - 2:21 pm
ACK
-
HHH
22h 37m
2 stops
$845United Airlines
Mon, Jun 29 - Fri, Jul 3
United Airlines Logo
1:45 pm - 10:15 am
HHH
-
ACK
20h 30m
1 stop
United Airlines Logo
10:53 am - 1:02 pm
ACK
-
HHH
26h 09m
1 stop
$873United 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 5 days was to Boston, at $251 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 5 days was $251.

Can I save money by flying with a layover from Hilton Head Island to Massachusetts?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $580 on average.

Find deals

Good to know

Cheapest flight$188
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 11686 reviews
7.9Crew
6.4Food
7.2Comfort
6.8Entertainment
7.5Boarding
Airline reviews

Flight had mechanical issues and it was delayed 30 mins - some of us boarded and then had to deplane.

8.0 ExcellentLydia, Jun 2026
SDF - DFW
Read more American Airlines reviews

Flight had mechanical issues and it was delayed 30 mins - some of us boarded and then had to deplane.

technology worked well and everything ran smoothly. The seats are quite cramped so please don't try to re-engineer the cabin to squeeze more bodies on board.

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

Flight was delayed due to connecting passengers. Lack of snack options bad. Sitting in Aisle, last cart run pulled the cart directly into my knee. Rude awakening.

We sat on plane at gate delayed without communication as to why we were just sitting there

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

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)