BOS - HHH

$126 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 5/23. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$251
Typical prices: $501-$282
American Airlines
Sat 5/30Sat 6/6
BOS - HHH • Non-stop
Cheapest one-way
$126
Typical prices: $278-$539
American Airlines
Sat 5/23
BOS - HHH • Non-stop
Nonstop flights
Sat
You can fly direct with American Airlines. Average duration is 2h 59m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top airlines
Cheapest • from $251 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Top layover airports
Cheapest • Avg $396 (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 27% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 21% price drop
Most popular
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

Sat, May 30 - Sat, Jun 6
American Airlines Logo
8:47 am - 11:46 am
BOS
-
HHH
2h 59mnonstop
American Airlines Logo
3:39 pm - 6:17 pm
HHH
-
BOS
2h 38mnonstop
$251American Airlines
Sat, Jun 13 - Wed, Jun 17
American Airlines Logo
12:10 pm - 3:09 pm
BOS
-
HHH
2h 59mnonstop
American Airlines Logo
11:40 am - 3:55 pm
HHH
-
BOS
4h 15m
1 stop
$261American Airlines
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 - 11:22 pm
HHH
-
BOS
7h 22m
1 stop
$271Delta
Mon, Jun 8 - Tue, Jun 16
Delta Logo
6:00 am - 11:31 am
BOS
-
HHH
5h 31m
1 stop
Delta Logo
4:15 pm - 10:28 pm
HHH
-
BOS
6h 13m
1 stop
$273Delta
Tue, Jul 7 - Fri, Jul 10
Delta Logo
6:00 am - 11:29 am
BOS
-
HHH
5h 29m
1 stop
Delta Logo
12:11 pm - 10:43 pm
HHH
-
BOS
10h 32m
2 stops
$276Delta
Sat, Jul 4 - Wed, Jul 8
American Airlines Logo
11:41 am - 2:26 pm
BOS
-
HHH
2h 45mnonstop
American Airlines Logo
2:48 pm - 8:10 pm
HHH
-
BOS
5h 22m
1 stop
$281American Airlines
Thu, Jul 9 - Fri, Jul 10
Delta Logo
6:00 am - 3:29 pm
BOS
-
HHH
9h 29m
2 stops
Delta Logo
12:11 pm - 10:43 pm
HHH
-
BOS
10h 32m
2 stops
$282Delta
Sat, May 30 - Thu, Jun 4
American Airlines Logo
8:47 am - 11:46 am
BOS
-
HHH
2h 59mnonstop
American Airlines Logo
5:21 pm - 12:40 am
HHH
-
BOS
7h 19m
1 stop
$285American Airlines
Sat, Jun 6 - Mon, Jun 8
American Airlines Logo
12:10 pm - 3:09 pm
BOS
-
HHH
2h 59mnonstop
American Airlines Logo
2:43 pm - 8:59 pm
HHH
-
BOS
6h 16m
1 stop
$286American Airlines
Thu, May 28 - Wed, Jun 3
Delta Logo
8:00 am - 3:33 pm
BOS
-
HHH
7h 33m
1 stop
Delta Logo
4:16 pm - 10:25 pm
HHH
-
BOS
6h 09m
1 stop
$291Delta
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 May.

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 February, where the average cost of round-trip tickets is $574 and $456 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 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$126
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 54% 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 $126 for a one-way ticket and $251 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 $352 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 $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 $194 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 8452 reviews
8.5Crew
7.8Comfort
7.2Food
7.8Entertainment
8.1Boarding
Airline reviews

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

6.0 GoodAnonymous, May 2026
PDX - MSP
Read more Delta reviews

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

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

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

No screens or meal options. Freezing cold. Dirty seats. Left late.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

There was a screen but no earphones that could use the older input so I could listen to anything.

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

The small flights with Valet Luggage has a poor service

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

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

Information on your arrival and departure airports