BOS - HHH

$119 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 11/18. 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

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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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

Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
6:00 am - 10:59 amBOS-HHH
4h 59m1 stop
American Airlines Logo
11:30 am - 4:24 pmHHH-BOS
4h 54m1 stop
$217American Airlines
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Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
7:00 am - 2:57 pmBOS-HHH
7h 57m2 stops
American Airlines Logo
3:27 pm - 10:33 pmHHH-BOS
7h 06m1 stop
$222American Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
American Airlines Logo
11:04 am - 6:33 pmBOS-HHH
7h 29m2 stops
American Airlines Logo
12:52 pm - 7:54 pmHHH-BOS
7h 02m2 stops
$227American Airlines
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Mon, Feb 9 - Sun, Feb 15
American Airlines Logo
8:30 am - 2:59 pmBOS-HHH
6h 29m1 stop
American Airlines Logo
4:19 pm - 10:30 pmHHH-BOS
6h 11m1 stop
$233American Airlines
Find Deal
Mon, Feb 9 - Sun, Feb 15
American Airlines Logo
6:00 am - 2:59 pmBOS-HHH
8h 59m2 stops
American Airlines Logo
4:19 pm - 10:30 pmHHH-BOS
6h 11m1 stop
$238American Airlines
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Mon, Oct 20 - Fri, Oct 24
Delta Logo
6:00 am - 11:37 amBOS-HHH
5h 37m1 stop
Delta Logo
4:10 pm - 9:27 pmHHH-BOS
5h 17m1 stop
$297Delta
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Mon, Oct 20 - Fri, Oct 24
United Airlines Logo
6:00 am - 11:16 amBOS-HHH
5h 16m1 stop
United Airlines Logo
11:57 am - 4:18 pmHHH-BOS
4h 21m1 stop
$317United Airlines
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Mon, Oct 20 - Fri, Oct 24
Delta Logo
6:00 am - 11:37 amBOS-HHH
5h 37m1 stop
Delta Logo
12:17 pm - 10:20 pmHHH-BOS
10h 03m2 stops
$327Delta
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Mon, Mar 30 - Wed, Apr 8
United Airlines Logo
8:30 am - 3:12 pmBOS-HHH
6h 42m1 stop
United Airlines Logo
4:00 pm - 11:17 pmHHH-BOS
7h 17m1 stop
$398United Airlines
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Mon, Oct 20 - Fri, Oct 24
United Airlines Logo
6:00 am - 11:16 amBOS-HHH
5h 16m1 stop
United Airlines Logo
11:57 am - 6:56 pmHHH-BOS
6h 59m2 stops
$407United Airlines
Find Deal

Everything you should know

Top airlines
American Airlines
Cheapest • from $217 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Video guide: How to find cheap flights to Hilton Head Island
Watch video
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When to travel
December
Cheapest • 31% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$217
Overall average: $248
American Airlines
Wed 12/3Wed 12/10
BOS - HHH • 1 stop
Cheapest one-way
$119
Typical prices: $270-331
American Airlines
Tue 11/18
BOS - HHH • 1 stop
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We hope you love your trip to Hilton Head Island!
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’s the cheapest day of the week to fly from Boston to Hilton Head Island?

The average price of all round-trip flights from Boston to Hilton Head Island clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Hilton Head Island on a Saturday and more expensive on a Thursday. On your return trip to Boston, you should consider flying back on a Thursday, and avoid Tuesdays for better deals.

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 $248 (return) on average. On the other hand, the most expensive months are February and April, where the average cost of round-trip tickets is $507 and $453 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 1 stop layover the cheapest option at $316 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonDecember
Cheapest flight$119
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 26% 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 $119 for a one-way ticket and $217 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 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 $618 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 7967 reviews
8.5Crew
7.3Food
7.9Entertainment
7.9Comfort
8.2Boarding
Airline reviews

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

2.0 MediocrePatricia Lynn, Oct 2025ATL - EYW
Read more Delta reviews

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

Cramped seating for me. Luckily it wasn’t a long flight

Lounge in Lagos is terrible, food on board from Lagos to Atlanta was horrible. Only bright spot the cabin crew were awesome.

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

Late FA meant slow boarding. WiFi did not work. I’m a medium plus sized passenger. The seatbelt was for the first time ever barely fitting. And we delayed on the tarmac 40 min

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

Flight is clean and ontime. Crew is friendly. Snack can be better and the internet connection is poor

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

My husband and I had boarded the flight from Denver to Chicago, and one of the last passengers to get on the plane opened the overhead bin above my husband's seat and threw his bag out of the bin to make space for his own. He said, "Mine is bigger!" The flight attendant supported the new passenger. They didn't care that my husband has two artificial knees and must have the foot room in front of his seat to be able to fit his legs in -- and to be able to stand, much less walk, at the end of the flight. I have never seen this happen before, and it was a disaster.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

I was in first class. The outlets at my seat did not work. The plane was shabby and run down. I had prepurchsed a day subscription for internet that was not redeemable. I had to repurchase the internet for my flight and then it didn’t work anyway. Quite disappointed in what was supposed to be the launch of a great vacation.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

We were delayed for a “couple of maintenance issues.” They were resolved rather quickly but a computer glitch caused someone in the airport to have to bring a physical copy of the paperwork so we could leave. I don’t know where they had to drive from to get to our plane but it took forever & we were 1 1/2 hrs late in leaving. The flight itself was fine.

You can plug your phone in & use their wifi to watch movies, etc, but the plane’s wifi was disconnected for most of the flight.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Very below average , plane from Dallas to Toyko was very poor designed plane. I had to sit for 13 hours next to fat man. Really bad seat and entertainment screen sucked

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

The Phildalphia to Allentown portion was a BUS, not a plane. All was as expected.

Very crowded flight but what can you expect these days?? Crew was accommodating.

We didn't take off until an hour after we boarded.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

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

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