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 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 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% 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.

Everything you should know

Cheapest round-trip
$317
Overall average: $357
American Airlines
Tue 3/10Tue 3/17
BOS - HHH • 1 stop
Cheapest one-way
$126
Typical prices: $148-$247
American Airlines
Tue 3/3
BOS - HHH • 1 stop
Video guide: How to find cheap flights to Hilton Head Island
Watch video
Watch video
Watch video
Watch video
Top airlines
American Airlines
Cheapest • from $317 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 29% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
December
Cheapest • 19% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
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

Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
12:15 pm - 4:44 pm
BOS
-
HHH
4h 29m
1 stop
American Airlines Logo
12:23 pm - 5:57 pm
HHH
-
BOS
5h 34m
1 stop
$317American Airlines
Wed, Apr 1 - Wed, Apr 8
American Airlines Logo
8:00 am - 3:41 pm
BOS
-
HHH
7h 41m
1 stop
American Airlines Logo
6:39 pm - 11:07 pm
HHH
-
BOS
4h 28m
1 stop
$321American Airlines
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
8:35 am - 3:01 pm
BOS
-
HHH
6h 26m
1 stop
American Airlines Logo
3:31 pm - 10:48 pm
HHH
-
BOS
7h 17m
2 stops
$322American Airlines
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
6:00 am - 3:01 pm
BOS
-
HHH
9h 01m
2 stops
American Airlines Logo
3:31 pm - 10:48 pm
HHH
-
BOS
7h 17m
2 stops
$327American Airlines
Wed, Apr 1 - Tue, Apr 7
American Airlines Logo
8:00 am - 3:41 pm
BOS
-
HHH
7h 41m
1 stop
American Airlines Logo
2:54 pm - 11:52 pm
HHH
-
BOS
8h 58m
2 stops
$360American Airlines
Wed, Mar 4 - Sat, Mar 7
American Airlines Logo
7:15 am - 11:53 am
BOS
-
HHH
4h 38m
1 stop
American Airlines Logo
6:20 pm - 10:40 pm
HHH
-
BOS
4h 20m
1 stop
$365American Airlines
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
9:00 am - 3:41 pm
BOS
-
HHH
6h 41m
1 stop
American Airlines Logo
3:31 pm - 8:21 pm
HHH
-
BOS
4h 50m
1 stop
$387American Airlines
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
6:00 am - 3:01 pm
BOS
-
HHH
9h 01m
2 stops
American Airlines Logo
4:11 pm - 10:22 pm
HHH
-
BOS
6h 11m
1 stop
$392American Airlines
Wed, Apr 1 - Wed, Apr 8
American Airlines Logo
6:00 am - 2:22 pm
BOS
-
HHH
8h 22m
2 stops
American Airlines Logo
11:03 am - 3:34 pm
HHH
-
BOS
4h 31m
1 stop
$394American Airlines
Sat, Apr 4 - Wed, Apr 8
American Airlines Logo
9:57 am - 4:01 pm
BOS
-
HHH
6h 04m
1 stop
American Airlines Logo
11:03 am - 3:34 pm
HHH
-
BOS
4h 31m
1 stop
$395American Airlines
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.

Find cheap flights to Hilton Head Island
Find cheap flights to Hilton Head Island

Planning a trip from Boston to Hilton Head Island? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

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 $408 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 3 weeks before departure, which saves you about 29% 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$126
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 13% 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 $317 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?

    JetBlue, American Airlines, 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 Airbus A220-300 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 $413 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

  • 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.

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 8162 reviews
8.5Crew
8.1Boarding
7.9Comfort
7.8Entertainment
7.2Food
Airline reviews

Prior to takeoff, the pilot told us there was a possibility of not being able to land and going to Portland. Well that happened, we took off and then did 8 loops around Spokane before the pilot told us we ran out of fuel and had to go to Portland. So for a 35 minute flight we have now been on the plane for 3 hours (boarded at 6:50 am and landed in Portland at 10:30). Then, we just sat in Portland's airport with no updates of when we can start heading back. All of a sudden, our pilots and crew just left, leaving us stranded in a different city and state. We continued to sit in Portland until we finally got a new crew assigned and boarded the plane (This was from 10:30-2). We then sat on the plane for an additional hour before take off because they had to count us multiple times. We finally landed in Spokane at 3:55 PM. So a flight that should have taken at max an hour took us 10 hours and we missed the majority of the recruiting event we went for.

2.0 MediocreKeenan, Feb 2026
GEG - SEA
Read more Delta reviews

Prior to takeoff, the pilot told us there was a possibility of not being able to land and going to Portland. Well that happened, we took off and then did 8 loops around Spokane before the pilot told us we ran out of fuel and had to go to Portland. So for a 35 minute flight we have now been on the plane for 3 hours (boarded at 6:50 am and landed in Portland at 10:30). Then, we just sat in Portland's airport with no updates of when we can start heading back. All of a sudden, our pilots and crew just left, leaving us stranded in a different city and state. We continued to sit in Portland until we finally got a new crew assigned and boarded the plane (This was from 10:30-2). We then sat on the plane for an additional hour before take off because they had to count us multiple times. We finally landed in Spokane at 3:55 PM. So a flight that should have taken at max an hour took us 10 hours and we missed the majority of the recruiting event we went for.

It was delayed but other than that it was great.

Got on the plane and sat there for an hour before departure.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

They double booked seats, the gate staff changed my ticket as I was boarding she went over to the computer and changed it without telling me. She messed up an entire three row section for me and others. Other travelers were outraged but the gate staff were so rude, so condescending saying it wasn't their problem to solve. I would rate this a zero if I could. Will not fly Delta again I'll stick with United and American.

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

Everything except the food and entertainment. It was a great experience though

Bad food, bad service, cold cabin with no additional blankets when asked for (they told me they don’t provide additional blankets). I’m a frequent traveler and this is one of the worst companies I traveled with (by the way I thought that I booked my ticket with Lufthansa but I didn’t see that the flights were handled by United).

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

The attendant on board was amazing. She should be doing business/first international long haul.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

the plane was so hot!! the air-conditioning was barely blowing. The flight was delayed, and we had to sit on the hot plane before take off for an extended amount of time, waiting on international passengers. Would not have been so bad if it was not so hot. They said it would get better after take off, but it did not.

They are always late and seats was also not having working charger

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

did not have enough meal for first class passengers so offer us snack

Arrived 40 min early which was great - sat in runway for 35 min so no gain. Then waited for luggage 45 min. They need to staff accordingly knowing its one of the busiest week in Phx

My flight got rerouted due to crew rest. I was sent to Dallas customer service was not very polite. Was given a $40 room voucher for Motel 6 and $12 to eat with. It delayed me by a day. Where if I would have just stuck with my original flight Arizona was delayed to Cleveland and I could have made it home. They put me on a 9:00 flight out of Dallas to Cleveland without my knowledge or consent. When originally I was told it would be 8:45 a.m. on February 1st. I told them I could not take the 9:00 flight because I did not have anybody to pick me up from the airport at that time. I'm extremely disappointed in how I was treated. And I will not fly American Airlines again.

I am very appreciative of the help provided to me by Dennis and Whitney. I had lost my phone at EWR airport and they were very kind in assisting me. This included advice on how to file a report and also helping me connect with family. The pilot was also great about keeping passengers updated on the flight progress with regular communications over the system.

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

Old equipment, needs upgrade and seat comfort. Internet didn't work 75% or the time.

The screens were inoperable for movies and such, but everything else was just fine

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

No included food for a 5 hour flight and the entertainment was only accessible if you had wired headphones (not provided). Otherwise though, great and smooth flying and customer service.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

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

Information on your arrival and departure airports