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 2/17. 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
$251
Overall average: $326
American Airlines
Sat 1/10Sat 1/17
BOS - HHH • 1 stop
Cheapest one-way
$126
Typical prices: $204-$294
American Airlines
Tue 2/17
BOS - HHH • 1 stop
Video guide: How to find cheap flights to Hilton Head Island
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When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 9% compared to booking last minute.
Insights
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Insights
Insights
When to travel
December
Cheapest • 19% price drop
April
Most popular
Good to know
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+1
+1
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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

Sat, Jan 10 - Sat, Jan 17
American Airlines Logo
6:41 am - 12:20 pm
BOS
-
HHH
5h 39m1 stop
American Airlines Logo
3:29 pm - 10:22 pm
HHH
-
BOS
6h 53m1 stop
$251American Airlines
Wed, Jan 28 - Sat, Jan 31
American Airlines Logo
8:03 pm - 12:20 pm
BOS
-
HHH
16h 17m2 stops
American Airlines Logo
3:29 pm - 8:33 pm
HHH
-
BOS
5h 04m1 stop
$252American Airlines
Sat, Jan 10 - Sat, Jan 17
American Airlines Logo
6:41 am - 12:20 pm
BOS
-
HHH
5h 39m1 stop
American Airlines Logo
3:29 pm - 9:29 am
HHH
-
BOS
18h 00m2 stops
$253American Airlines
Sun, Jan 11 - Sat, Jan 17
American Airlines Logo
7:35 pm - 12:20 pm
BOS
-
HHH
16h 45m2 stops
American Airlines Logo
3:29 pm - 9:29 am
HHH
-
BOS
18h 00m2 stops
$256American Airlines
Wed, Jan 28 - Sat, Jan 31
American Airlines Logo
7:35 pm - 12:20 pm
BOS
-
HHH
16h 45m2 stops
American Airlines Logo
12:54 pm - 8:13 pm
HHH
-
BOS
7h 19m2 stops
$257American Airlines
Sat, Jan 10 - Sat, Jan 17
American Airlines Logo
6:00 am - 12:20 pm
BOS
-
HHH
6h 20m2 stops
American Airlines Logo
3:29 pm - 9:29 am
HHH
-
BOS
18h 00m2 stops
$258American Airlines
Wed, Feb 11 - Sat, Feb 14
American Airlines Logo
6:00 am - 2:59 pm
BOS
-
HHH
8h 59m2 stops
American Airlines Logo
11:02 am - 7:41 pm
HHH
-
BOS
8h 39m2 stops
$261American Airlines
Sun, Jan 11 - Sat, Jan 17
American Airlines Logo
6:43 am - 12:20 pm
BOS
-
HHH
5h 37m1 stop
American Airlines Logo
3:29 pm - 10:22 pm
HHH
-
BOS
6h 53m1 stop
$264American Airlines
Sun, Jan 4 - Wed, Jan 7
American Airlines Logo
5:53 am - 10:44 am
BOS
-
HHH
4h 51m1 stop
American Airlines Logo
3:29 pm - 7:12 am
HHH
-
BOS
15h 43m2 stops
$266American Airlines
Mon, Feb 9 - Sun, Feb 15
American Airlines Logo
8:03 pm - 12:20 pm
BOS
-
HHH
16h 17m2 stops
American Airlines Logo
6:22 pm - 10:41 pm
HHH
-
BOS
4h 19m1 stop
$270American 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’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 $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 $483 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 2 weeks before departure, which saves you about 9% 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 with an average 10% drop 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 $149 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?

    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?

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

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

    The two airlines most popular with KAYAK users for flights from Boston to Hilton Head Island are Delta and American Airlines. With an average price for the route of $399 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $386 and an overall rating of 7.2.

  • 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 3 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 8008 reviews
8.5Crew
7.9Comfort
7.9Entertainment
7.3Food
8.1Boarding
Airline reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

10.0 ExcellentMargaret, Dec 2025
BOS - PIT
Read more Delta reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Did not understand a single word the attendant said on the pa system. I was glad it was not an emergency.

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

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

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

Information on your arrival and departure airports