Find cheap flights from Caribbean Islands to Hilton Head Island

Find cheap flights from Caribbean Islands to Hilton Head Island

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Boston (BOS)
Hilton Head Island
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Fri 12/11
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Top airlines flying Caribbean Islands to Hilton Head Island

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,809 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Had a great professional crew even the pilot walked through the plane to answer questions"
Cons: "Nothing delta returns to the top"

Pros: "Getting to know the crew who served me in delta one was great! Food service was done pretty quickly and good snacks available."

Pros: "Super friendly staff, great service and delicious food. The competition has nothing compared to Delta. We’re switching"

Pros: "Crew not so much!"
Cons: "A bit friendlier ...had no ice??"

Pros: "Everything"
Cons: "Nothing"

Cons: "Superb service on board and at kiosk!"

Pros: "Flight attendant coughed in my face twice without covering her mouth while I was seated and she was passing out drinks and snacks"

Pros: "Smooth, efficient and timely."
Cons: "Seats weren’t assigned until at the gate even though checked in 18 hours before. Bag drop was horrible. No self service. Was inline for about 45 minutes."

Pros: "Crew was great"
Cons: "Thermostat broke, wi fi didn’t work. Temp 60 degrees entire trip. Sucked"

Pros: "The check in process was smooth and the flight crew were pleasant"
Cons: "some of the TSA crew were rude/seemed to be doing a lazy job with helping load items on the belt"

Cons: "Boarding process was really poor. Long line for just dropping a bag off that I already paid for."

Pros: "Quick board, quick flight and everything went smoothly."
Cons: "Someone to rub my feet, but that’s wishful thinking."

Pros: "Boarding and crew were professional and courteous."
Cons: "Media interface system and Gogo inflight app are not synced and I could not listen to the movie I was watching. No subtitles offered for in flight movies. Someone farted before we deplaned and it was quite unpleasant. Also I wish the automatic seat assignments took my height into account."

Pros: "Crew was so friendly and helpful!"
Cons: "My suitcase arrived damaged."

Pros: "For me the boarding was of fast"
Cons: "The food"

Pros: "Quick flight"
Cons: "I wish there was a way to access the delta movies in small planes that don’t have seat back entertainment"

Cons: "Snacks"

Pros: "Crew was good. It was great to be able to watch a movie, TV, or play a game to pass the time."
Cons: "More let room when someone puts back their seat."

Pros: "Emergency exit window seat"
Cons: "Punctuality 7hrs delays over 2 flights is unacceptable Ruined the first day of my trip"

Pros: "Friendly crew"
Cons: "No food was served"

Pros: "the worst thing that I've traveled in my life I do not travel again by delta 3 hours without food and without taking or water we were not given that service is the worst its employees are a disaster"
Cons: "the worst thing that I've traveled in my life I do not travel again by delta 3 hours without food and without taking or water we were not given that service is the worst its employees are a disaster"

Pros: "Left on time, landed early"
Cons: "Asked a crèw member to put my bag in the overhead , didn't like his attitude,also asked him for a soda, didn't get it, got it from another attendant"

Cons: "Flighted delayed due to mechanical issues. Missed connecting 400pm flight. Next flight was 10:25 pm."

Pros: "Delta cramps people into these planes and forces you to put your bags under a seat because they stuff at the overhead spaces. They nickel and dime you for every single thing. There was even one person I saw who had to pay for his headphones to listen to the onboard entertainment. I think Delta should quit being so cheap with the profits they make and give it back to your flying customers. It borders on gouging."
Cons: "Delta cramps people into these planes and forces you to put your bags under a seat because they stuff at the overhead spaces. They nickel and dime you for every single thing. There was even one person I saw who had to pay for his headphones to listen to the onboard entertainment. I think Delta should quit being so cheap with the profits they make and give it back to your flying customers. It borders on gouging."

Cons: "Na"

Pros: "No issues"

Pros: "Crew was good, plane was clean. We left on time and got in a bit early."
Cons: "Don't like the Comfort plus seats that have the dividers vs basic arm rests. TSA is a JOKE, got the random strip search where they pulled apart every nook and cranny of my personal bag and carry on item. Relieved me of my PLASTIC corkscrew that I've traveled with for 15 years. Almost missed the flight and I was there plenty early."

Pros: "Good flight overall"
Cons: "Although I have priority status -The ground crew in Amsterdam gave me hard time with 7 extra Pounds, and I was trying to take it out of the suitcase to no avail. Eventually the agent I was checking in with got busy, I went to a new agent, and with a flick of a keyboard he approved the extra rate based on my status, without even have my to request it."

Pros: "I love flying Delta and my flight to Australia was incredible. I like the fact that I can check two bags free and the free inflight messaging and entertainment. Some of the staff were very polite and friendly."
Cons: "The seat I was in was broken. It moved and I was stuck sitting on metal. There was no leg room. The plane used going to Australia was a lot roomier this plane was old. Some of the flight attendants were very unfriendly and seemed to be bothered by the fact they had to do their job. The entertainment system had to be rebooted multiple times and the usb on the seats didn’t work. They ran out of food during lunch."

Cons: "The attitude of the employees."

Pros: "The flight entertainment and crew were great. They had a lot of the latest movies available to watch, though I'm not sure you'd be able to watch if you didn't have your own headphones (I did). The crew were friendly and helpful. I got a cold cup of coffee when it should have been hot, and they corrected it immediately."
Cons: "They charge you for everything: sitting in an aisle or window seat ($15); checking one piece of luggage ($25); for food, even on a five hour flight, save for complementary snacks like a granola bar or pretzels. I paid $11 for a tiny sandwich (it fit in the palm of my already small hands). I will definitely get good at the airport next time. It may be just as expensive, but at least it will be filling."

Cons: "Z"

Pros: "Comfortable seats"

Pros: "Humor"
Cons: "Pasta on board is heavy, lighter meal option is preferred"

Cons: "The flight was quite smooth."

Pros: "No food or entertainment on short flight"

Pros: "It landed safely"
Cons: "Delayed take-off, one plane for hour or so."

Pros: "Seats were comfortable"

Cons: "It was announced that there would be lunch shortly after takeoff and then a snack about 2 hours before landing. The lunch was ok, but then the snack (multiple small items) was offered about 4 hours before landing and then an additional snack (mini pot pie) was offered about 2 hrs before landing. This is too much action for people who are trying to get some sleep. Also, abrupt and hard landing."

Pros: "The flight was very quick."
Cons: "They didn't serve us water."

Pros: "Service from the crew."
Cons: "Quality and comfort of seats. Quality of food. The TV screen was from the 80s."

Pros: "Business as usual and we actually arrived abit earlier than projected. Cudos to the pilot and crew."

Pros: "Good service and food"
Cons: "My non-reclining first class seat was a disappointment on this long flight. The flight was full, so there was no re-seating option."

Pros: "I would like the airline service to do more for our veterans. Especially the 100% disabled veterans"
Cons: "Seats not comfortable enough"

Pros: "Overall this was a great flight. The entertainment system wasn't always working, but I was reading and its a short flight, so I didn't really care."

Pros: "Read above"
Cons: "Read above"

Pros: "Plane was clean and staff were friendly"
Cons: "The snack options were quite average"

Pros: "The crew was really fantastic the service was very good."

Pros: "Everything"
Cons: "No complaints"

Cons: "Very full flight when covid cases are at all time highs. Not possible to social distance in these conditions."

Cons: "Flight left on time."

Cons: "Flight was late for no apparent reason"

Cons: "We were delayed because we were waiting on a crew member. It was kind of ridiculous"

Pros: "Quick smooth flight"
Cons: "No entertainment available"

Pros: "Direct flight, quick and easy. Dinner, breakfast and complimentary drinks were nice."
Cons: "The plane for this flight was lacking current amenities such as power supplies for devices and individual tv screens. The gate crew was a bit rude commenting on my tardiness to board although it was due to my flight arriving late from Denver which I feel they should have known was not my fault."

Cons: "Have coach passengers prepay for meals"

Pros: "All was good"
Cons: "Nothing to complain about."

Pros: "It was quick, on time."
Cons: "Beverage service did not exist."

Pros: "I flew business so it made a difference in the overall experience. Crew was pleasant and served beverages as soon as I boarded. Also, received a pillow and blanket as it was chilly on the plane."
Cons: "No complaints, everything was perfect. It's worth it to spend the extra cash and fly business."

Pros: "It was the most uncomfortable flight I can remember"

Cons: "It’s an absurd to pay so dearly on airline tickets is not to have a booster snack, and no blanket, that’s very cold!"

Pros: "The movie selection was great!"

Pros: "I liked the arts and craft show that was showing on the plane."
Cons: "As I came into the airport I went to a kiosk to check in and the attendant at the kiosk basically took over my passport and started pushing buttons that I never asked her to push. I eventually got my boarding passes only to find I wasn’t assigned a seat for the first flight and I will get it later at the gate. After getting through security my name was called for a extra security screening which I thought was interesting since I have Global Entry and am an American citizen. Weird. Because my name was called I had to get to the gate early. Upon arriving to the gate the gate agent confirmed I have extra security screening and she would assign my seat soon. After waiting some time she assigned me to a middle seat in the last row of the plane! After boarding someone came and sat next to me that was overweight and should have been charged for 2 seats. With such a long flight it’s the least American can do."

Pros: "Pilot was informative."

Pros: "The crew handled the emergency very professionally"

Pros: "The crew made a real effort to make everyone comfortable."

Pros: "We were on a new plane and each seat had power."
Cons: "I was in the window seat near the back and there was a steel box (guessing for the electricity to the seat-back) that took up a third of the width for my feet."

Pros: "Nothing"
Cons: "Nothing was good! Horrible horrible airline!"

Cons: "Going to aircraft by bus in the cold with long wait for bus departure"

Cons: "The flight was delayed an hour, which would have made us miss our connecting flight back to our home destination. We switched flights in order to make it home at a decent hour and not spend our entire day and night in an airport. We arrived home and they did not transfer two of our three checked bags to our flight, thus making it highly inconvenient upon our arrival home with no luggage."

Pros: "Everyone was nice. Flight left on time an landed early."
Cons: "The front row for the exit is too small. The diagram i looked at said it was an exit row on the 2nd leg of my flight. It wasnt!! Uncomortable for my legs. Im 6'3"

Pros: "The crew was friendly."
Cons: "Boarding is chaotic. They don't check the group number when passengers board."

Pros: "Flight was not completely full so I got an empty seat next to me."
Cons: "We were delayed due to some balance issues."

Pros: "I was not seated with my husband when we were given our tickets and they were gracious enough to give us exit row seats by each other."
Cons: "As we were boarding the plane they told us that we needed to check our bags. No other explanation was given. I brought a carry on so that I didn’t have to check my bag. I thought maybe it was because there wasn’t enough overhead space, but as we got on the plane the overhead bins were very large and extra space was left as they began to close up the bins for take off. It was extremely annoying and I felt I was given no choice."

Pros: "VERY GOOD"

Pros: "Lo siento. No habla ingles. Me muy guapo."
Cons: "No entertainmento."

Pros: "Direct service, legroom in main cabin"
Cons: "Flight bought by American Airlines. Not the same quality as British airlines flight."

Pros: "Flight crew kept us advised of the weather situation (thunderstorms/turbulence). Did a good job of finding a route that was fairly smooth. Overall very pleasant flight and crew."
Cons: "It's an MD-80. Need old cigarette-lighter style plug to be able to charge anything. No inflight entertainment unless you use snail-speed Go-Go internet service."

Cons: "Horrible delays. Delta doesn't have these problems."

Pros: "The crew was nice."
Cons: "We had to walk outside to board the plane. My husband has two bad hips and we had to walk up a flight of stairs to board the plane. The plane was extremely small and our sits were located in the rear of the plane. The bathroom had an unpleasant odor."

Pros: "Movies"
Cons: "As always, just too many damn people on the plane. Who are all of these people? What are they doing?"

Cons: "No headset for entertainment"

Pros: "One hour delay caused a missing of a connect flight"

Pros: "Clean and new airplane. Crew was very nice"
Cons: "People in front of us were reclining the entire time and our seats right behind them were tight. Did not like having to pay extra for seats"

Pros: "Crew members and staff taking tickets were courteous"
Cons: "Tiny seats - actually flight was cancelled just before boarding time. I flew AA from State College to Philadelphia then."

Pros: "They were accommodating to my boot on my foot in the boarding process."
Cons: "Comfort and room in the seats. The temperature was very hot as well."

Pros: "Companion in flight nice Korean girl... We chatted trough all flight time"
Cons: "Arrived and luggage did not arrive and had to open a claim and had to go back to pick my luggage next day, not pleasant considering I live in Juarez Mexico and had to cross the border all tired and fed up with this incident"

Pros: "The crew relax and smile"
Cons: "very small seats"

Pros: "Delayed 2 hours out of charlotte. Missed flight to Madrid. Newark people are rude"
Cons: "Look above"

Pros: "I liked that the plane was clean, that the staff consisted of somewhat normal, more mature people, and that water and carry-ons are free."
Cons: "I felt that having to pay $50 extra for a seat when I checked in was pretty deceptive and unethical. I think most people would agree that when they purchase a boarding pass, it is assumed that it includes a seat. Having to pay extra for a seat was something I did not plan for and it was out of my budget, but I had no choice, because I had to get home somehow! I'll be going without groceries this week due to this unplanned expense."

Pros: "Ease of checking in by agent. Courteous and friendly staff. On time departure"

Pros: "Crew attitude to work in a plane model that should be retired."
Cons: "Insane for AA to still use a 757 for a intercontinental flight."

Pros: "Great movie selection, including ones currently in theaters."
Cons: "Only received pretzels for snacks, while others received cookies."

Pros: "Service is excellent"
Cons: "I didn't like the seats are to small"

Pros: "Crew on flight to Charleston was nice"
Cons: "I was supposed to make the trip from BNA to CHS at 2:30, we were delayed over 1.5 hours, making me miss this flight by 5 mins. Then I was put on 10pm flight which was cancelled! They couldn't get me to HHH until 6pm the following day. I would have missed my entire conference. The closest they could get me was a 10pm flight to charleston, then I had to rent (AND PAY FOR) a car and drive 2 hours to HHH in the middle of the night. The customer service people were less than helpful. They aren't allowed to help you make car reservation. My flight on the way back from HHH to BNA was a similar story. Thankfully my connecting flight was delayed an hour or there was no way I would have made it."

Pros: "Poor"
Cons: "No food chips chips very POOR POOR"

Pros: "The single flight attendant was very friendly and down to earth, and was keen to share her experience with us."
Cons: "De Havilland Dash-8's can be a bit noisy, and they seem to be the only planes they fly into Hilton Head. However, that isn't to say you're unable to get sleep on them, because my partner and I both slept the entire flight- the vibrations are only slightly disconcerting. Departure was about 15 minutes late out of Charlotte."

Cons: "delay , i am of the opinion that american airline will be late every time . it took two days to go to kingston jamaica from miami intl on 8-4-16 this should be 1. 30 hrs. that was verry poor and return on 8-28-16 flight was delay , i could understand this but two days is a bit too long . ,this happen to me so i not happy . frankie arboine"

Cons: "The flight never happened. Our outgoing flight from HHI to Charlotte was delayed until it was eventually canceled with no reason given and we were rerouted through Savannah, an hour away with no notification and so the return flight had to be changed too because our car was in Savannah"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Caribbean Islands to Hilton Head Island

Airlines flying from Caribbean Islands to Hilton Head Island have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters

Mandatory masks

Masks required on board, masks provided

Social distancing seating

Middle seats unavailable to book

Pre-flight testing

Testing for antibodies, testing for symptoms

Book cheap flights from Caribbean Islands to Hilton Head Island

Recent round-trip flight deals

2/5
Fri
1 stop
Delta
7h 24m
KIN - HHH
2/9
Tue
1 stop
Delta
6h 35m
HHH - KIN
2/5
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2 stops
American Airlines
28h 21m
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2/9
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American Airlines
41h 57m
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3/31
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Delta
24h 37m
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4/4
Sun
1 stop
Delta
12h 21m
HHH - KIN
2/23
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American Airlines
9h 53m
PLS - HHH
2/27
Sat
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American Airlines
8h 36m
HHH - PLS
2/23
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American Airlines
7h 40m
PLS - HHH
2/27
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American Airlines
4h 42m
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3/31
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American Airlines
20h 20m
KIN - HHH
4/4
Sun
2 stops
American Airlines
12h 31m
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2/5
Fri
2 stops
American Airlines
26h 46m
ANU - HHH
2/9
Tue
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American Airlines
43h 17m
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1/2
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American Airlines
27h 30m
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1/4
Mon
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American Airlines
43h 42m
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3/31
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Multiple Airlines
11h 22m
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Multiple Airlines
8h 40m
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Multiple Airlines
11h 37m
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Multiple Airlines
8h 30m
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5/3
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American Airlines
25h 14m
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5/4
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American Airlines
19h 03m
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5/3
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American Airlines
23h 25m
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American Airlines
17h 26m
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5/3
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American Airlines
6h 25m
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American Airlines
6h 31m
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