$128 Find Cheap Flights from Caribbean to Raleigh - Compare and Save

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Cheap Flights from Caribbean to Raleigh

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Raleigh

Mon, Nov 2 - Mon, Nov 9
Frontier Logo
11:20 am - 9:17 amSJU  San Juan Luis Munoz Marin Intl-RDU Raleigh-Durham
22h 57m1 stop Orlando
Frontier Logo
9:30 pm - 2:43 pmRDU  Raleigh-Durham-SJU San Juan Luis Munoz Marin Intl
16h 13m1 stop Orlando
$128Frontier
Fri, Oct 30 - Thu, Nov 5
Frontier Logo
10:20 am - 12:48 pmSJU  San Juan Luis Munoz Marin Intl-RDU Raleigh-Durham
26h 28m1 stop Orlando
Frontier Logo
11:10 am - 1:25 pmRDU  Raleigh-Durham-SJU San Juan Luis Munoz Marin Intl
25h 15m1 stop Fort Lauderdale
$169Frontier
Sat, Oct 17 - Sat, Oct 24
Multiple Airlines Logo
1:00 pm - 4:34 pmSJU  San Juan Luis Munoz Marin Intl-RDU Raleigh-Durham
3h 34mnonstop
Multiple Airlines Logo
7:08 pm - 10:49 amRDU  Raleigh-Durham-SJU San Juan Luis Munoz Marin Intl
15h 41m1 stop Miami
$210Multiple Airlines
Mon, Nov 2 - Mon, Nov 9
Multiple Airlines Logo
3:55 pm - 6:39 pmSJU  San Juan Luis Munoz Marin Intl-RDU Raleigh-Durham
3h 44mnonstop
Multiple Airlines Logo
9:30 pm - 2:43 pmRDU  Raleigh-Durham-SJU San Juan Luis Munoz Marin Intl
16h 13m1 stop Orlando
$229Multiple Airlines
Thu, Oct 15 - Sun, Oct 18
JetBlue Logo
10:30 am - 5:49 pmSJU  San Juan Luis Munoz Marin Intl-RDU Raleigh-Durham
7h 19m1 stop New York John F Kennedy Intl
JetBlue Logo
5:30 pm - 9:02 pmRDU  Raleigh-Durham-SJU San Juan Luis Munoz Marin Intl
3h 32mnonstop
$278JetBlue
Wed, Nov 4 - Mon, Nov 9
American Airlines Logo
2:26 pm - 11:29 pmSXM  Simpson Bay Princess Juliana-RDU Raleigh-Durham
10h 03m1 stop Charlotte Douglas
American Airlines Logo
5:00 am - 2:26 pmRDU  Raleigh-Durham-SXM Simpson Bay Princess Juliana
8h 26m1 stop Miami
$296American Airlines
Wed, Nov 4 - Mon, Nov 9
American Airlines Logo
3:26 pm - 12:24 amSXM  Simpson Bay Princess Juliana-RDU Raleigh-Durham
9h 58m1 stop Miami
American Airlines Logo
6:00 am - 4:31 pmRDU  Raleigh-Durham-SXM Simpson Bay Princess Juliana
9h 31m2 stops Philadelphia Miami
$296American Airlines
Thu, Oct 29 - Sun, Nov 1
JetBlue Logo
2:23 pm - 6:07 pmSJU  San Juan Luis Munoz Marin Intl-RDU Raleigh-Durham
3h 44mnonstop
JetBlue Logo
7:30 pm - 11:55 pmRDU  Raleigh-Durham-SJU San Juan Luis Munoz Marin Intl
3h 25mnonstop
$298JetBlue
Fri, Nov 13 - Sat, Nov 14
Southwest Logo
3:45 pm - 11:45 pmSTT  Saint Thomas Island Cyril E King-RDU Raleigh-Durham
9h 00m1 stop Baltimore/Washington
Southwest Logo
6:10 am - 1:50 pmRDU  Raleigh-Durham-STT Saint Thomas Island Cyril E King
6h 40m1 stop Baltimore/Washington
$320Southwest
Thu, Dec 3 - Sun, Dec 6
Southwest Logo
10:45 am - 5:40 pmSJU  San Juan Luis Munoz Marin Intl-RDU Raleigh-Durham
7h 55m2 stops Orlando Nashville Intl
Southwest Logo
4:10 pm - 1:05 amRDU  Raleigh-Durham-SJU San Juan Luis Munoz Marin Intl
7h 55m1 stop Baltimore/Washington
$339Southwest
Useful Info

Good to know

Low season

January

Cheapest flight

$128
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from San Juan to Raleigh

FAQs for booking flights from Caribbean to Raleigh

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

    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 Caribbean to Raleigh.

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

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

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

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

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

Reviews of the top 5 airlines serving from Caribbean to Raleigh

 
Need help choosing which airline to fly with from Caribbean to Raleigh? 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
SouthwestOverall score based on 4216 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

I understand the delays caused by the storm, but that doesn’t mean the systems had to be chaotic. The app showed one thing, the screens showed something else, and the gates kept changing every 10 minutes. It was a nightmare trying to figure out where to go.

2.0 MediocreWatimosin, Oct 2026
Read more Southwest reviews

I understand the delays caused by the storm, but that doesn’t mean the systems had to be chaotic. The app showed one thing, the screens showed something else, and the gates kept changing every 10 minutes. It was a nightmare trying to figure out where to go.

It was good. Last flight was delayed but I always say that is in God's plan

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

I liked the boarding by group and numbers. I didn't like my inability to guarantee our seats together. I didn't like the $8/flight for Internet, but I did appreciate the inflight movie options on their app. I didn't like that there were no charging stations on the seats during either of our flights. One flight was over 3 hours.

I never like the fact that if I don't check in exactly 24 hours before the flight time, I get to board C, and that means sitting between 2 individuals. I would like assigned seating in the airplanes.

Flight only half full. Room to spread out. Newer plane. Very satisfied.

Surprisingly the coffee was pretty good and they had a gluten free bar handy!

Delta exceeded my expectations! I am beyond satisfied. Thank you!

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

Smooth boarding, pleasant and professional lady checking us in. Crew service was excellent, again pleasant, but professional. Nice touch-down on landing! Thank you Delta. 💗

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! 💗

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

My overall experience with JetBlue was pretty poor and disappointing. We originally booked a DIRECT flight home from Boston on 9/28 at 8:00pm even though it cost more than the non direct flights. With no reason other than "unforeseen circumstances", our flight home Monday was cancelled and we were rebooked on a 7:00am flight on 9/29 with a layover in JFK. We were traveling with sick kids coming home from a funeral of a loved one and needed to be at work on Tuesday so paying extra for a flight home Monday was something we had to do. The original direct flights were considerably more expensive than the non direct flights- so I don't understand how Jetblue did absolutely NOTHING to compensate or right their mistake. We will not be booking with them in the future because they are not reliable and they showed no remorse nor did they make any attempt to make things right. The least they could have done was credit the difference in cost of flight because I know our original flights cost more than the one we were rebooked on. Once again- we will not be flying with them in the future and will advise family and friends to be aware of the risk you run when giving them your business. Do better.

The flight attendant was snarky and the flight took off very late. I know it was an issue with air traffic control and the runways in Boston, so not really anyone's fault, but very frustrating, I missed an important meeting because of rgr delay. They didn't offer headphones to watch the TV, but luckily I remembered my own and was able to enjoy watching a movie.

Terrible. We originally booked a direct flight from BOS to MCO on 9/28 at 8:00pm and it was cancelled due to unforeseen circumstances and the flight we were rebooked on was on 9/29 at 7:00am with a layover in JFK. We were traveling with sick kids so leaving at such an early hour was absolutely miserable, and on top of that we all missed work which we couldn’t afford. On top of that- we paid a fortune for our flights to be direct without a layover and the flights with layovers were cheaper so at the very minimum we should have been refunded the difference. With absolutely no explanation or sympathy from JetBlue- we will avoid using them in the future due to the fact they aren’t reliable nor do they correct their mistakes.

Experience with JetBlue was poor. We were originally suppose to fly home on a direct flight on Monday the 28th at 8:00pm and we it was canceled due to “unforeseen circumstances” and we were rebooked on a 7am flight on Tuesday the 29th with a layover in JFK. Traveling with sick kids and waking up at an ungodly hour was miserable, and not only that it caused all of us to miss work. We intentionally flew our Monday on a direct flight and the direct flight was far more than the non direct flights on any given day. There was no compensation provided let alone a reasonable explanation. When you are charging people those type of prices for domestic same coast flights- you should be at least refunding the cost difference of the flights if you are rebooking them on a cheaper flight. I will never fly JetBlue again because they are unreliable and don’t correct their mistakes.

Wasn’t very happy with our flight home due to the fact it was cancelled with absolutely no reason. It was a direct flight at 8:00pm on Monday and they rebooked us for a 7am flight on Tuesday with a layover. Traveling with sick kids, getting up that early was miserable and on top of that we all missed a day of work that we couldn’t afford to with absolutely no apology or compensation from JetBlue. The original cost of the flights were astronomical because we flew out on Monday over Tuesday and also we paid extra for the direct flight then we would have for the flight with a layover. Super disappointed Jetblue truly could have cared less. Will avoid them in the future due to the fact they aren’t reliable nor compassionate for the inconvenience these changes cost their clients.

No WiFi, no power to charge phone, confusing boarding, delays

There is a considerable amount of people that use the wheel chair pre boarding along of large groups of family / friends. This is not right should be limited only to the person in need and the airline assistant. Some of these people use overhead bins that do not belong to them. The aircraft had a non functional wifi . The service was bad.

It was so nice! I wish that we can have direct flights to El Salvador 😊😊

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

It was a pretty smooth flight, I tend to get mini anxiety attacks during flights, however, this time was pretty smooth and I was able to relax. The only thing, I was having issues to connect to the Flyfi internet. I was not able to connect at all, I turned off my phone a couple times and didnt work.

Our trip to Spain turned into a stressful ordeal with cockpit issues and FAA air traffic disruptions. Our American Airlines flight from Raleigh to JFK was delayed nearly four hours, causing us to miss our connections to Madrid and Jerez. We were left stranded in New York with children, even running out of diapers while trying to sort everything out. American refused to cover hotels or rental cars, leaving us to arrange and pay for them ourselves. The delays also disrupted our prepaid rental car reservations in Spain. It was a frustrating and expensive start to a family trip we had spent months planning.

Flight was delayed significantly at take off and landing. Confusion of gate assignment with back and forth. Overall, makes for a very unpleasant experience that appears to come down to inept operational management.

Flight was delayed which isn’t the airline’s fault, but the communication around it was terrible. I left the lounge to show up at the gate to board at the time in my app, and the flight in front of mine was still boarding and the inbound plane hadn’t even taken off yet. Delays were slow to show up in my app. Improved communication could have let me have a more pleasant experience in the lounge vs waiting 1.5 hours at the gate.

Horrible experience flying with American. Flight was delayed due to inbound flight delay. Fine, it happens. Then, we were delayed an additional almost 30 minutes due to the paperwork for departure having a "clerical error." Then, upon landing at the destination airport we were stuck on the plane for an HOUR after we landed and pulled up to the gate because apparently there was another plane. An hour waiting for the gate 12:30 AM when the flight has already been delayed due to operational error feels like a complete failure of the ability to do the one thing they need to do apart from actually have the plane takeoff and land. Very disappointing.

Overall a good experience, however Wifi was not working on the flight.

Flight was on-time, boarding was flawless and the crew was friendly.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

It would have been nice if American tried to care.

We arrived 25 minutes early only to be told our gate was occupied and so we sat for close to 30 minutes to pull into a gate. That’s not an early arrival!

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

When I was boarding my departure from Raleigh to Orlando I was inappropriately scolded by a female dog named Mia because I didn’t pay in advance for my carry on bag ($75). Frontiers website is confusing regarding pre-paying for carryons so it was a simple mistake. I also had paid for “upfront plus” meaning me and my son were seated in the front row with no one in the middle seat ($450 upgrade). When we were boarding Mia said “sir, you didn’t pay for your carryon” in a not so polite tone and told me to get out of line and come back to the counter to pay for my carryon. The way they had the retractable rope left me no room to circle back without making the people behind me move so I just stood there and then she said a second time “sir!! Go pay for your carryon” in an embarrassing tone. I then moved their rope so I could get back to the counter when a second female dog then asked “are you done!?!?” because I had said “do you want me to bulldoze the people behind me?” I then said you do realize I paid over $400 for upfront plus so I was certainly not trying to sneak a carryon bag without paying. Long story short, I am soooo done with discount airlines!!! By the time you pay for all the “extras” you might as well have paid for Delta Southwest or American! Frontier airlines sucks and I was embarrassed by a female dog named Mia!!!

Zero issues with this flight. Crew was outstanding and flight was super. Plane was clean and fine. The seats need more padding and water should be provided without cost. I recognize it's Frontier but there are some things that should still be part of the flight. But still very satisfied with the experience and quality.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

One crew member was rude about our bags. Be nice about it. We don’t fly a lot. And the fact that you have to pay for a carry on is ridiculous

The flight attendant was arguing with a passenger before takeoff. The passenger was frustrated but the flight attendant should have handled it with grace, but instead she was nasty and rude. The seats were comfortable and the flight was uneventful. I wish we didn’t have to pay for drinks or snacks but that’s what you get with a budget airline.

Did not get the extra leg room i paid for.

Direct flight I like, Did not like all the delays

Delayed over 2 hours on the way there, and back, no free drinks, no free water, no Wifi, bathroom dirty!

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