BOS - HHH

$179 Find Cheap Flights from Boston to Hilton Head Island

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Hilton Head Island departing on 5/20. 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 Hilton Head Island

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

Cheapest round-trip
$329
Overall average: $433
United Airlines
Thu 4/16Tue 4/21
BOS - HHH • 1 stop
Cheapest non-stop
$500
American Airlines
Sat 5/30Sat 6/6
BOS - HHH • Non-stop
Nonstop flights
Sat
You can fly direct with American Airlines. Average duration is 0
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
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Top airlines
Cheapest • from $329 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $396 (round-trip)
Shortest trip • 4h 28m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 7% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 19% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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We hope you love your trip to Hilton Head Island!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Hilton Head Island 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 Boston to Hilton Head Island

Thu, Apr 16 - Tue, Apr 21
United Airlines Logo
7:00 am - 2:16 pm
BOS
-
HHH
7h 16m
1 stop
United Airlines Logo
3:05 pm - 9:59 pm
HHH
-
BOS
6h 54m
1 stop
$329United Airlines
Tue, Apr 7 - Tue, Apr 14
United Airlines Logo
10:05 am - 3:30 pm
BOS
-
HHH
5h 25m
1 stop
United Airlines Logo
4:11 pm - 9:54 pm
HHH
-
BOS
5h 43m
1 stop
$334United Airlines
Tue, Apr 7 - Tue, Apr 14
United Airlines Logo
5:45 am - 3:30 pm
BOS
-
HHH
9h 45m
2 stops
United Airlines Logo
4:11 pm - 9:54 pm
HHH
-
BOS
5h 43m
1 stop
$339United Airlines
Tue, Apr 7 - Tue, Apr 14
United Airlines Logo
5:45 am - 2:16 pm
BOS
-
HHH
8h 31m
2 stops
United Airlines Logo
4:11 pm - 11:59 pm
HHH
-
BOS
7h 48m
2 stops
$344United Airlines
Sat, May 9 - Wed, May 13
United Airlines Logo
10:00 am - 3:41 pm
BOS
-
HHH
5h 41m
1 stop
United Airlines Logo
3:08 pm - 11:59 pm
HHH
-
BOS
8h 51m
2 stops
$348United Airlines
Fri, May 8 - Tue, May 12
United Airlines Logo
8:30 am - 3:41 pm
BOS
-
HHH
7h 11m
1 stop
United Airlines Logo
4:39 pm - 11:59 pm
HHH
-
BOS
7h 20m
2 stops
$349United Airlines
Mon, Apr 20 - Thu, Apr 23
Delta Logo
5:10 pm - 3:20 pm
BOS
-
HHH
22h 10m
2 stops
Delta Logo
4:00 pm - 7:25 am
HHH
-
BOS
15h 25m
1 stop
$356Delta
Thu, Sep 10 - Mon, Sep 14
Delta Logo
6:00 am - 11:23 am
BOS
-
HHH
5h 23m
1 stop
Delta Logo
4:00 pm - 10:27 pm
HHH
-
BOS
6h 27m
1 stop
$357Delta
Thu, Sep 10 - Mon, Sep 14
Delta Logo
6:00 am - 3:20 pm
BOS
-
HHH
9h 20m
2 stops
Delta Logo
4:00 pm - 9:31 pm
HHH
-
BOS
5h 31m
1 stop
$362Delta
Tue, Apr 28 - Thu, Apr 30
Delta Logo
9:30 am - 3:20 pm
BOS
-
HHH
5h 50m
1 stop
Delta Logo
4:00 pm - 8:21 am
HHH
-
BOS
16h 21m
1 stop
$364Delta
Booking Insights

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Hilton Head Island, 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 Boston to Hilton Head Island is December, where tickets cost $292 (return) on average. On the other hand, the most expensive months are February and April, where the average cost of round-trip tickets is $456 and $433 respectively.

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

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 2 stops layover the cheapest option at $342 on average.

How far in advance should I book a flight from Boston to Hilton Head Island?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Hilton Head Island, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Hilton Head Island, you should book around 2 weeks before departure, which saves you about 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$179
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Boston to Hilton Head Island

When to book flights from Boston to Hilton Head Island

Are your dates flexible? Find out the best times to travel from Boston to Hilton Head Island 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 Boston to Hilton Head Island

  • Are there lounges at Boston Logan International Airport?

    There are lounges in the airport that you can access regardless of the class of service you are flying. Air France Lounge is in Terminal E at the airside around gate 4. Admirals Club by American Airlines is located in terminal B, at the airside near gate B4. If you are in Terminal B, visit the United club situated at the airside on Level 3 near gate 24. The lounge in Terminal C and The Club in Terminal E are other lounge options.

  • Are there pet relief areas at the airport?

    Boston Airport has a pet relief area if you travel with your furry friend. Use the pet relief area in Terminal E across from gate E7. Hilton Head International Airport has two outdoor relief areas at the baggage claim area's south and north ends.

  • Can I get assistance at Boston Logan International Airport?

    If you have any concerns or questions, you need not stress. Visit the Boston Logan Airport information booth. The public service booths are located near the baggage claim area at the arrivals of every Terminal.

  • How can I get downtown from Hilton Head Airport?

    The means of transport you choose will determine how much you are likely to spend. If you are late for your appointment, use a taxi as a transfer mode. However, if you are on a budget, use a bus as a public means of transport.

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

    In the last 3 days, the lowest price for a flight from Boston to Hilton Head Island was $179 for a one-way ticket and $329 for a round-trip.

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

    A passport is not required to fly from Boston to Hilton Head Island.

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

    On your way to Hilton Head Island, you’ll fly out from Boston Logan Intl. You’ll be landing at Hilton Head Island.

  • Which airlines offer Wi-Fi service onboard planes from Boston to Hilton Head Island?

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Boston to Hilton Head Island flight route.

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

    The Embraer 175 is the aircraft model that flies most regularly on the Boston to Hilton Head Island flight route.

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

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Boston and Hilton Head Island, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Boston to Hilton Head Island, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Boston to Hilton Head Island are Delta and United Airlines. With an average price for the route of $362 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $527 and an overall rating of 7.4.

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

    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 Boston to Hilton Head Island.

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

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

    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 Hilton Head Island with an airline and back to Boston with another airline. Booking your flights between Boston and HHH 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 Boston to Hilton Head Island?

    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 Hilton Head Island from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Boston to Hilton Head Island

  • Looking for a cheap flight? 25% of our users found flights on this route for $383 or less round-trip.
  • Spend your night at Boston Logan International Airport (BOS) if you have an early flight. At the airport, you can book your room at Hilton Boston Logan Airport, connected by a sky bridge to Terminals A and E. There are nearby hotels with free airport shuttle service. Hyatt Regency Boston Harbor, Courtyard by Marriott Boston Logan Airport, Comfort Inn & Suites, and Embassy Suites by Hilton Boston at Logan Airport are some of the recommended hotels.
  • Boston International Airport has shower facilities for travelers who would love to freshen up before their flight. Admirals Club by American Airlines has a shower facility. The lounge is located in Terminal B at the airside near gate B4. United Club in Terminal B, at the airside near gate 24, is another option.
  • Two major airports serve the Boston region. Rhode Island T.F. Green International Airport (PVD) is 48 miles away, while Boston Logan International Airport is 1 mile away from the city center. PVD airport always has short security lines and cheaper flights than BOS, with long security lines and insane traffic. However, Boston-Logan has better amenities and several flight options.
  • If you lose your property at Hilton Head Airport (HHH), you need not worry. If you lose your items at the Terminal, visit the baggage claim area. For items lost at the security checkpoint, visit the security department. If you forget your items on board, contact your airline. Alternatively, you can call the Lost and Found department directly or complete the online form indicating the type of item lost, the date, and the place you last traced the item.
  • Boston Logan has eight designated baby care facilities for mothers traveling with their toddlers. If you are in Terminal A, use the rooms at the landside and the airside. Alternatively, use the Mamava Suites in Terminals B, C, and E. These suites offer changing tables, chairs, a power outlet, and sinks.

Prefer to fly direct from Boston to Hilton Head Island?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Boston Logan Intl to Hilton Head Island.
Find which airlines fly direct from Boston Logan Intl Airport to Hilton Head Island Airport, which days they fly and book direct flights.

Direct departures

Boston Logan Intl to Hilton Head Island

Saturday

American Airlines

American Airlines

See more direct flights

Direct returns

Hilton Head Island to Boston Logan Intl

Saturday

American Airlines

American Airlines

See more direct flights

Reviews of the top 4 airlines serving from Boston to Hilton Head Island

 
See real verified KAYAK customer reviews for airlines flying from Boston to Hilton Head Island. 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 Boston to Hilton Head Island? 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.
7.9
DeltaOverall score based on 8321 reviews
8.1Boarding
7.9Comfort
7.8Entertainment
7.2Food
8.5Crew
Airline reviews

The cabin temperature was nice and cool. The wifi was not working.

8.0 ExcellentMatt, Mar 2026
SEA - SJC
Read more Delta reviews

The cabin temperature was nice and cool. The wifi was not working.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

As previously noted, this flight was great: departure was timely, the crew was friendly and attentive, and wifi connectivity was seamless. In particular, I appreciated that the flight attendant just told me to stow the laptop right before takeoff/landing, and trusted me to do so (which I did!).

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

I will never fly ANA again. They lost one of my large pieces of checked luggage, the heaviest one with the most valuable items in it, and they said they will not send me an email unless they can't find it, even though the paper they gave me to track the status of my lost luggage requires a code from an email they are supposed to send me so I can do baggage tracing. They claim to be an international airline, but they also insist on calling a Japanese telephone number to confirm where to send the lost baggage if they find it. It is impossible to find an actual contact email address for customer support on their website, and their AI chatbot is unhelpful, directing you to a webpage that says it is for contact information but does not have any actual email addresses or phone numbers listed on it. My seat in economy did not recline at all, even though I was not sitting in an exit row nor the very back row. I had to sit in the fully upright position for over ten hours of international travel. Awful experience overall.

My flight was canceled a few hours before boarding. I was rebooked on Copa airlines and missed an important meeting .

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Delays with no explanation. It could have been handled better.

Ceiling fell down and had to have maintenance come and duct tape it up. No WiFi on the flight.

A first class seat should fit a fat person, and this doesn't. The trays in the armrest are less functional than an ordinary tray in the back of the seat.

The flight attendant was friendly and efficient. The temperature was kept nice and cool. The plane was nice, but filthy. There were visible spills on my tray table. The gate agent was somewhat rude with her announcements and in speaking with other customers.

I appreciate that I finally got the seat I paid extra for this time. Thank you

I would have liked vegetarian and gluten free options for evening dinner time flight. I would have like a pillow on the international overnight flight . The veg wrap and oaten desert on the international flight was good

The experience at checkin for my American Airlines flight from Sacramento to LAX was very good including the assistance I received in getting my bags checked in and boarding passes printed. Was pleasantly surprised the my bags were checked through all the way to my destination at Clark International Airport in Angeles, Philippines.

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

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

Information on your arrival and departure airports