$99 Find Cheap Flights from Raleigh to Caribbean Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Raleigh to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
San Juan
3h 32mNonstop
from $206per person
Saint Thomas Island
6h 13m2 stops
from $259per person
Simpson Bay
6h 13m2 stops
from $278per person
Nassau
4h 45m2 stops
from $306per person
Montego Bay
4h 58m2 stops
from $340per person
Oranjestad
6h 10m2 stops
from $343per person
George Town
5h 04m2 stops
from $367per person
Punta Cana
3h 25mNonstop
from $372per person
Explore the map
Booking Insights

KAYAK's insights & trends for Raleigh to Caribbean Islands flights

Get data-powered insights and trends into flights from Raleigh to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Raleigh to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Raleigh found in the last 5 days was to Montego Bay, at $147 round-trip. The most popular route is from Raleigh (RDU) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $184.

What is the cheapest time of day to fly to Caribbean Islands?

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $351 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $381.

Can I save money by flying with a layover from Raleigh to Caribbean Islands?

No, with an average price for the route of $402, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Raleigh to Caribbean Islands?

The cheapest month for flights from Raleigh to Caribbean Islands is January, when tickets cost $444 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $597 and $594 respectively.

What’s the cheapest day of the week to fly from Raleigh to Caribbean Islands?

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Raleigh to Caribbean Islands. For your return ticket, we recommend flying on a Friday and avoiding Mondays for the best deals.

How far in advance should I book a flight from Raleigh to Caribbean Islands?

To get a below average price on the flight from Raleigh to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low season

September

Cheapest flight

$99
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Raleigh to Nassau

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Raleigh to Caribbean Islands?

    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 Raleigh to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Raleigh to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Raleigh to Caribbean Islands 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 Raleigh to Caribbean Islands?

    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 from Raleigh to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Raleigh to Caribbean Islands?

    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 from Raleigh to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between Raleigh and Caribbean Islands per day?

    There is a maximum of 1 nonstop flight a day that takes off from Raleigh and lands in Caribbean Islands, with an average flight time of 3h 32m. The most common departure time is 5:00 pm and most flights take off in the afternoon. Each week, there are 5 flights.

Reviews of the top 5 airlines serving from Raleigh to Caribbean Islands

 
Need help choosing which airline to fly with from Raleigh to Caribbean Islands? 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.
8.2
Breeze AirwaysOverall score based on 322 reviews
8.8Crew
8.2Comfort
8.4Boarding
6.8Food
6.8Entertainment
Airline reviews

I thought I paid for a round trip for carry-on and my ticket only had one way when I purchased a round trip Didn't make sense to me .Not what you want to hear when it's time to go home.

8.0 ExcellentMark, Sep 2026
Read more Breeze Airways reviews

I thought I paid for a round trip for carry-on and my ticket only had one way when I purchased a round trip Didn't make sense to me .Not what you want to hear when it's time to go home.

Support for wheel chair was not good. Desk did not open until 2 hours before takeoff not check in time.

Boarding process was super smooth and the staff and crew were wonderful. Seats made me feel like I was being bent forward. Might be because I'm shorter and the puffy head rest pushes my head down. I would have liked to have been able to remove it

What entertainment!? Snack i bought was unusual and in very small quantity. Very limited selection of snacks to buy. Taste was mediocre.

It was easy and very comfortable! The crew was accommodating and cheerful. I enjoyed myself!

Our flight was delayed 7 hours. Due to a change in equipment we were downgraded from "Nicest" to "Nicer," even having to pay for a soft drink. Disappointing. To Breeze's credit that issued a $100 flight credit. A refund would have been more appreciated.

Lady at check in counter helped me get a seat in the cut row all to myself.

Our gate was changed twice, but since they were super close it wasn't an issue. We were delayed 90 mins or so, which wasn't great, but sometimes that's just what happens. Communication was the issue. We weren't kept informed about delays--with more information I would have gotten a real meal, taken a "bio break" and purchased a new book. Because another. flight was being updated more frequently about their delays, I thought ours would be shorter and stayed close by. It left me feeling more frustrated than was necessary.

The flight was rescheduled and canceled. I had to go with another airline last minute to honor my school commitment. The reimbursement is a joke -$150 for a one way plane ticket.

The flight itself was A+ but boarding sucked. They boarded all passengers at once, and as a result I did not get to put my carryon in an overhead bin near me so I had to wait till near the end to deplane.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

No food or drink, Not much conversation with crew. They didn't come through to check on people. There were no charging stations or wifi to watch movies. It was like being on a bus in the air.

This flight was originally delayed by ~45 minutes; which is fine. However, there were additional delays due to late offboarding of the prior flight, unclear issues with the boarding process, delays on the tarmac, and exceptionally long taxiing. None of these issues were communicated proactively. Additionally, the flight had exceptionally rough turbulence, which led to a very uncomfortable flight and no traditional beverage service. Again, this is understandable, but it was not communicated up-front by the flight team.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Two delays on two separate planes with parts they could not easily find and replace.

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

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Flight was 3 hours late so only had an OK experience

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Staff and flight attendants were very polite. Flight was smooth. My seat on the plane was a bit broken so it would not stay in upright position but it was fine for the most part.

I didn’t have a seat assignment and my seat was very dirty on the flight from Frankfurt to Budapest.

Turbulent taking off & landing to Dulles from Raleigh. Flight from Dulles to Tokyo very good!!

Food is terrible. Flight is outdated and seats are not comfy.

Good flight. On time. Boarding and seating was easy. Crew were really friendly, yet professional. Bathroom (by cockpit) was small but serviceable. Some the seats were showing some notable wear & tear, but were comfy. Very happy UA customer. TY! 🤛🏽💗

Boarding was easy. RDU gates can get crowded, be prepared to be patient. Flight was smooth, with excellent service. Pilots really provided a lot of visibility into flight details. Plane and seats were clean and serviceable. TY!

All flights were on time and boarding was issue free

Water service would be great. The way they board is terrible. Slow passengers first😂😂 They need to smart up a bit

Got automatically assigned middle seats unless you fork out extra money for a seat assignment, not impressed.

Late by nearly 2 hours due to taking that long to change a tire on the plane.

It’s love good long way travel!! I always want more give me price down i want ever month travel I miss travel only North Carolina to Thailand in my love her !!

I found the seats ergonomically uncomfortable forcing the body to seat slightly hunched. For a short flight I worked on adjustments but for a longer flight, it would be difficult.

For some unknown reason, my checked bag didn't arrive at the same time. I got to my destination about 30 minutes late (5pm) and my bag was delivered to my hotel at 2:06am.... in the past 4 flights with AA, they been delayed and I've missed connections and my bags. Poor service.

Check in for 5am flight at RDU was hampered by American check in counters being seriously understaffed , was told even supervisor called out. Took so long in line for special services check in that we missed our 5am departure even after arriving at 3:30am. Had to be rescheduled to later flight from Charlotte to St Thomas.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

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

This flight never occurred because AA couldn’t get their act together.

Everything was great except boarding for the flight from Charlotte to Raleigh and seating from New Orleans to Charlotte.

For an over three hour long flight one pack of cookies was not enough.

KUDOS TO ALL THE CREW PROVIDING ASSISTANCE WITH PASSENGERS ON A WHEELCHAIR. ON BOTH FLIGHTS THEY HUSTLED TO TAKE MY RELATIVE TO CONNECTION ON TIME. THEY DESERVE A LOT OF CREDIT!

Good experience with this flight. Boarding was smooth with no issues. The short flight was good with quick drink & snack service. Nice easy way to get back from DC.

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

It's not JetBlues fault but there was a smell on the plane (possibly other travelers) and 3 children behind me that never quit whining. Soccor fans that were very loud. Pilot brought the plane down from high altitude quickly, dropping us hu dress of feet at a time. I've never felt that intense of dropping on other airlines (usually fly Southwest Airlines). But I arrived safely and I'm thankful for that.

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

I liked that boarding and take off were timely despite a 15 minute delay due to weather. The pilot communicated with us the entire flight keeping us informed re: turbulance and slight delays on the runway after we landed.

I didn't like the 2 hour delay and then mechanical issue once we were on board.

Realize ahead of a 6:30 am flight that you have a completely flat tire that needs replacement. They should have never boarded everyone. They kept us at the gate with the door closed for ALMOST but not quite 3 hours. The plane had been sitting there from the night before. At the 2 hour mark of sitting there, they came through with a bottle of water and cups. Never offered snacks. Never offered a real apology. People missed connecting flights completely. Absolutely no apology. Just yep you are going to miss your connection completely. I don’t know if you can get to your destination today. The new boy time there was a seemingly heartfelt apology was when they said they were sorry and then fifer everyone an opportunity for a credit card. It was so poor. Lucky for us, our funeral was not the same day as our flight or we would have missed it. All for an avoidable repair that could have been done before we even set foot on the plane.

Boarding and take off from airport was on time. The crew and pilot were great!

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental