BOS - HHH

$154 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 7/18. 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
$299
Typical prices: $295-$426
American Airlines
Sa 7/18Mi 7/22
BOS - HHH • Non-stop
Cheapest non-stop
$289
American Airlines
Sa 8/29Sa 9/5
BOS - HHH • Non-stop
Nonstop flights
Sat
You can fly direct with American Airlines. Average duration is 2h 45m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
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Top airlines
Cheapest • from $299 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
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Top layover airports
Cheapest • Avg $340 (round-trip)
Shortest trip • 4h 53m (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 26% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
Good to know
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Good to know
Good to know
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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

Sa, Jul 18 - Mi, Jul 22
American Airlines Logo
11:30 am - 2:15 pm
BOS
-
HHH
2h 45mnonstop
American Airlines Logo
11:47 am - 6:04 pm
HHH
-
BOS
6h 17m
1 stop
$299American Airlines
Mi, Jul 29 - Mi, Aug 5
American Airlines Logo
10:13 am - 4:25 pm
BOS
-
HHH
6h 12m
1 stop
American Airlines Logo
5:16 pm - 10:13 pm
HHH
-
BOS
4h 57m
1 stop
$309American Airlines
Mi, Jul 29 - Mi, Aug 5
Delta Logo
5:30 am - 3:29 pm
BOS
-
HHH
9h 59m
2 stops
Delta Logo
4:18 pm - 9:47 pm
HHH
-
BOS
5h 29m
1 stop
$314Delta
Di, Jul 14 - Di, Jul 21
American Airlines Logo
10:13 am - 4:25 pm
BOS
-
HHH
6h 12m
1 stop
American Airlines Logo
11:47 am - 6:04 pm
HHH
-
BOS
6h 17m
1 stop
$318American Airlines
Mi, Jul 29 - Mi, Aug 5
Delta Logo
5:30 am - 3:29 pm
BOS
-
HHH
9h 59m
2 stops
Delta Logo
12:15 pm - 9:47 pm
HHH
-
BOS
9h 32m
2 stops
$319Delta
Di, Jul 14 - Di, Jul 21
Delta Logo
5:30 am - 3:29 pm
BOS
-
HHH
9h 59m
2 stops
Delta Logo
4:14 pm - 10:33 pm
HHH
-
BOS
6h 19m
1 stop
$323Delta
Do, Jul 9 - Do, Jul 16
Delta Logo
9:05 am - 3:29 pm
BOS
-
HHH
6h 24m
1 stop
Delta Logo
4:14 pm - 10:33 pm
HHH
-
BOS
6h 19m
1 stop
$324Delta
Do, Jul 9 - Mo, Jul 13
American Airlines Logo
10:13 am - 4:25 pm
BOS
-
HHH
6h 12m
1 stop
American Airlines Logo
11:47 am - 6:04 pm
HHH
-
BOS
6h 17m
1 stop
$327American Airlines
Sa, Jul 25 - Sa, Aug 1
American Airlines Logo
11:30 am - 2:15 pm
BOS
-
HHH
2h 45mnonstop
American Airlines Logo
2:45 pm - 5:21 pm
HHH
-
BOS
2h 36mnonstop
$328American Airlines
Mi, Jul 8 - Fr, Jul 17
Delta Logo
6:00 am - 3:29 pm
BOS
-
HHH
9h 29m
2 stops
Delta Logo
4:14 pm - 11:31 pm
HHH
-
BOS
7h 17m
1 stop
$329Delta
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.

How much is a round-trip flight from Boston to Hilton Head Island?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Boston to Hilton Head Island departing in July.

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 April and August, where the average cost of round-trip tickets is $576 and $460 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.

No, with an average price for the route of $308, prices are generally cheapest when you fly direct.

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 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$154
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 51% 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.

  • How many flights are there between Boston and Hilton Head Island per day?

    There is a maximum of 1 nonstop flight a day that takes off from Boston and lands in Hilton Head Island, with an average flight time of 2h 45m. The most common departure time is 11:00 am and most flights take off in the morning. Each week, there are 1 flights.

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

    In the last 5 days, the lowest price for a flight from Boston to Hilton Head Island was $154 for a one-way ticket and $299 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?

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

  • On which days can I fly direct from Boston to Hilton Head Island?

    You can catch a nonstop flight from Boston to Hilton Head Island on on Saturday.

  • 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 $363 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $408 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 $299 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.
7.8
DeltaOverall score based on 8442 reviews
7.8Comfort
7.2Food
8.1Boarding
8.5Crew
7.8Entertainment
Airline reviews

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

8.0 ExcellentAnonymous, Jun 2026
BOS - RDU
Read more Delta reviews

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

The flight was smooth, the crew was great but the plane was quite old

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

No complaints - left 20 minutes later than planned but still arrived on time.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

The flight was delayed, they didn’t even have water for the toilets or for drinks

It’s always a great time flying with united airlines.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

Attendants zipped through cabin so fast hardly anyone got the water they told us we could have in the short flight. Nothing else was offered.

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

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.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

Great experience. Good dinner and service. FA's were very nice and attentive.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

The business steward was absolutely amazing! Smiles and kindness! Wish all AA flights are like this one!

Never going to fly your airline again if it can be avoided.

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

Flight left 2 hours late with no explanation as to the delay

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

I was seated next to an autistic child who was out of control and had a child behind me kicking my seat for most of the trip. I will never fly JetBlue again. Ever. I don't care how cheap it is. It's terrible.

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

All airline travel outside of First or Business class is an ordeal to be endured. This trip was ok, small o, small k.

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

Information on your arrival and departure airports