HHH - BOS

$126 Find Cheap Flights from Hilton Head Island to Boston

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 Boston departing on 3/3. 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 Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Boston, 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 Boston, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$251
Overall average: $456
American Airlines
Tue 2/24Wed 2/25
HHH - BOS • 1 stop
Cheapest one-way
$126
Typical prices: $161-$272
American Airlines
Tue 3/3
HHH - BOS • 1 stop
Top airlines
American Airlines
Cheapest • from $251 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
April
Cheapest • 53% price drop
January
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Boston!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hilton Head Island to Boston (HHH-BOS)

 
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 Boston 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 Boston

Tue, Feb 24 - Wed, Feb 25
American Airlines Logo
5:19 pm - 10:15 pm
HHH
-
BOS
4h 56m
1 stop
American Airlines Logo
8:00 am - 3:41 pm
BOS
-
HHH
7h 41m
1 stop
$251American Airlines
Tue, Feb 24 - Wed, Feb 25
American Airlines Logo
5:19 pm - 11:59 pm
HHH
-
BOS
6h 40m
2 stops
American Airlines Logo
10:00 am - 3:41 pm
BOS
-
HHH
5h 41m
1 stop
$256American Airlines
Thu, Mar 5 - Wed, Mar 11
American Airlines Logo
2:58 pm - 9:50 pm
HHH
-
BOS
6h 52m
1 stop
American Airlines Logo
10:00 am - 3:41 pm
BOS
-
HHH
5h 41m
1 stop
$277American Airlines
Thu, Mar 5 - Wed, Mar 11
American Airlines Logo
2:58 pm - 10:48 pm
HHH
-
BOS
7h 50m
2 stops
American Airlines Logo
10:00 am - 3:41 pm
BOS
-
HHH
5h 41m
1 stop
$282American Airlines
Fri, Mar 20 - Mon, Mar 23
American Airlines Logo
4:11 pm - 10:22 pm
HHH
-
BOS
6h 11m
1 stop
American Airlines Logo
5:47 am - 10:33 am
BOS
-
HHH
4h 46m
1 stop
$298American Airlines
Fri, Mar 20 - Mon, Mar 23
American Airlines Logo
4:11 pm - 10:22 pm
HHH
-
BOS
6h 11m
1 stop
American Airlines Logo
6:00 am - 2:22 pm
BOS
-
HHH
8h 22m
2 stops
$303American Airlines
Thu, Mar 5 - Wed, Mar 11
American Airlines Logo
2:58 pm - 10:48 pm
HHH
-
BOS
7h 50m
2 stops
American Airlines Logo
6:00 am - 2:22 pm
BOS
-
HHH
8h 22m
2 stops
$343American Airlines
Thu, Mar 5 - Thu, Mar 12
American Airlines Logo
2:58 pm - 10:48 pm
HHH
-
BOS
7h 50m
2 stops
American Airlines Logo
6:00 am - 2:22 pm
BOS
-
HHH
8h 22m
2 stops
$348American Airlines
Wed, Jun 3 - Sun, Jun 7
American Airlines Logo
5:54 pm - 12:34 am
HHH
-
BOS
6h 40m
1 stop
American Airlines Logo
10:11 am - 5:09 pm
BOS
-
HHH
6h 58m
1 stop
$388American Airlines
Fri, Mar 20 - Mon, Mar 23
American Airlines Logo
6:15 pm - 11:59 pm
HHH
-
BOS
5h 44m
2 stops
American Airlines Logo
6:00 am - 2:22 pm
BOS
-
HHH
8h 22m
2 stops
$390American Airlines
Booking Insights

KAYAK's insights & trends for Hilton Head Island to Boston flights

Get data-powered insights and trends into flights from Hilton Head Island to Boston to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Hilton Head Island to Boston?

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 Boston, 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 Boston is April, where tickets cost $149 (return) on average. On the other hand, the most expensive months are February and June, where the average cost of round-trip tickets is $456 and $426 respectively.

Find deals

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 and prices are also 13% lower on average.
Flight from Hilton Head Island to Boston

When to book flights from Hilton Head Island to Boston

Are your dates flexible? Find out the best times to travel from Hilton Head Island to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Hilton Head Island to Boston

  • What is the cheapest flight from Hilton Head Island to Boston?

    In the last 3 days, the lowest price for a flight from Hilton Head Island to Boston was $126 for a one-way ticket and $251 for a round-trip.

  • Do I need a passport to fly between Hilton Head Island and Boston?

    No

  • Which airports will I be using when flying from Hilton Head Island to Boston?

    When flying out of Hilton Head Island you will be using Hilton Head Island. You will be landing at Boston, also known as Boston Logan Intl.

  • Which aircraft models fly most regularly from Hilton Head Island to Boston?

    The Embraer 170 is the aircraft model that flies most regularly on the Hilton Head Island to Boston flight route.

  • Which airline alliances offer flights from Hilton Head Island to Boston?

    oneworld is the only airline alliance operating flights between Hilton Head Island and Boston.

  • How does KAYAK find such low prices on flights from Hilton Head Island to Boston?

    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 Boston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hilton Head Island to Boston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Hilton Head Island 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 Boston?

    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 to Boston with an airline and back to Hilton Head Island with another airline. Booking your flights between Hilton Head Island and BOS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hilton Head Island to Boston?

    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 to Boston from Hilton Head Island 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 Boston

 
See real verified KAYAK customer reviews for airlines flying from Hilton Head Island to Boston. 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 Boston? 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 11207 reviews
6.9Entertainment
8.0Crew
6.4Food
7.5Boarding
7.2Comfort
Airline reviews

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

4.0 OkayBrandle, Jan 2026
DFW - MCO
Read more American Airlines reviews

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

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

Information on your arrival and departure airports

Hilton Head Island (HHH)
Boston (BOS)