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$44 Find Cheap Flights to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from the United States to Caribbean Islands departing on 11/10. 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.
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Search hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Caribbean Islands
These are the airlines KAYAK users have selected most often from within our search results for flights to Caribbean Islands

Best Caribbean Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cananonstop$188
Montego Bay
Montego Baynonstop$202
Santo Domingo
Santo Domingo1 stop$237
Oranjestad
Oranjestad1 stop$268
Nassau
Nassaunonstop$238
Simpson Bay
Simpson Bay1 stop$205
Kingston
Kingstonnonstop$236
Providenciales
Providencialesnonstop$280
Bridgetown
Bridgetown1 stop$194
Port of Spain
Port of Spain1 stop$162
George Town
George Townnonstop$236
Willemstad
Willemstad1 stop$392
St. John's
St. John'snonstop$303
Aguadilla
Aguadillanonstop$116
Puerto Plata
Puerto Platanonstop$341

Good to know

Low season

September

High season

December

Cheapest flight

$44
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from Boston to San Juan Airport

FAQs - booking Caribbean Islands flights

  • How long is the flight to Caribbean Islands?

    An average nonstop flight from the United States to Caribbean Islands takes 3h 54m, covering a distance of 1551 miles. The most popular route is New York - San Juan with an average flight time of 3h 50m.

  • What is the cheapest flight to Caribbean Islands?

    The cheapest ticket to Caribbean Islands from the United States found in the last 72 hours was $74. The most popular route is New York John F Kennedy Intl to San Juan Luis Munoz Marin Intl and the cheapest round-trip airline ticket found on this route in the last 72 hours was $117.

  • Which airlines fly to Caribbean Islands?

    JetBlue, Qatar Airways & United Airlines fly the most frequently from the United States to Caribbean Islands. The most popular route is from New York to San Juan, and JetBlue, Qatar Airways and Turkish Airlines fly this route the most.

  • What are the most popular destinations in Caribbean Islands?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (14% of total searches to Caribbean Islands). The next most popular destinations are Santo Domingo (12%) and Montego Bay (10%). Searches for flights to Oranjestad (9%), to Santiago de los Caballeros (7%) and to Nassau (6%) are also popular.

  • How does KAYAK’s flight Price Forecast tool help me choose the right time to buy?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a given destination and date is likely to change within 7 days, so travelers know whether to wait or book now.

See more FAQs

Top tips for finding cheap flights to Caribbean Islands

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Caribbean Islands flight deals.

Flights to Caribbean Islands: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Caribbean Islands 
JoseFlew with United AirlinesIAH-SJUSep 2024
Eat before your boarding. Buy snacks or anything you like before departure, also download a movie, music or an audio book to enjoy during your flight.
YvetteFlew with JetBlueMCO-BQNSep 2024
I liked that they changed there policy for people traveling Blue Basic they now can travel with one carryon and one backpack no extra charge
LuisFlew with SouthwestTPA-SJUJun 2024
Flight with Southwest! The crew is excellent and makes you feel secure during the flight. Only in Southwest you can flight with a carry on and two check bags without charges. Always clean airplanes and confortable.
TaniaFlew with Caribbean AirlinesMIA-POSJun 2024
Caribbean is the choice from Miami to POS. The immigration and TSA line in that area was shorter hence less stress and the flight crew was good. I was happy I chose Caribbean Airlines.
BFlew with JetBlueBOS-AUAJun 2024
Just long enough flight you need to plan on something to occupy your time. A book, a movie etc.
Verified travelerFlew with JetBlueBDL-SJUJul 2024
Bradley International Airport is a convenient and wonderful airport with many flights to San Juan de Puerto Rico.
Maria AlejandraFlew with FrontierJFK-SJUAug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix
BillFlew with DeltaATL-SKBMar 2024
Hope you have a newer plane where comfort plus really is comfort plus. 737-800 needs to retire.
NicoleFlew with United AirlinesEWR-POPApr 2024
Customer service accommodated my family to be seated together prior the flight! Thank God
Verified travelerFlew with United AirlinesEWR-SDQApr 2024
Early check in online, get on time for the flight
TamaraFlew with JetBlueJFK-NASMar 2024
Fly delta if you want a less rude experience.
Verified travelerFlew with Spirit AirlinesFLL-KINApr 2024
Check in very early Eat a complete meal before flying Don't be overweight
JamesFlew with FrontierSTL-PUJFeb 2024
Punta Cana airport- be ready for chaos once you get out of the airport. But it all works out well. A positive- our luggage was on the carousel as we got out of customs (so unlike STL!).
KerryFlew with United AirlinesIAH-POSDec 2023
There was no internet and it seems like there never is. Charge your devices and pre-download your movies or audio.
KarenFlew with Spirit AirlinesFLL-SJUJan 2024
I think spirit is your only nonstop. Just check all your charges first and learn how to do it yourself at the airport.

Top 5 airlines flying to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the United States to Caribbean Islands. 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 the United States 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.
8.0
DeltaOverall score based on 8884 reviews
8.6Crew
8.2Boarding
7.9Entertainment
7.9Comfort
7.3Food
Airline reviews

Flight heavily delayed. No food available despite purchasing an upgrade. No in cabin service.

2.0 MediocreScott, Oct 2024SLC - JFK
Read more Delta reviews

Flight heavily delayed. No food available despite purchasing an upgrade. No in cabin service.

We had a two hour delay in SL but to me the crew was so communicative and descriptive that it made it not a big deal. It was about safety first and I'd rather be way delayed than have a major issue during a flight. Also they automatically booked us on the next flight at our connection due to missing our connection flight. Everything went smoothly it was amazing. We are very pleased with our flights.

The woman in seat 1A was allowed to bring a dachshund dog onboard. It smelled terrible and the odor wafted throughout the first class cabin. This was clearly not a service dog and should be prohibited. I paid for the highest class of service, and this was a disservice. Why is Delta allowing this? I may reconsider my future flight choices.

Wifi did not work and they only served water, coffee, or tea.

The plane was very warm upon entering. This was a bigger problem as the weather was cold so people were dressed accordingly.

The crew was very polite as I have a few handicaps and everything was made pleasant. Check-in was easy as I was brought on board by the wheelchair assistant. One flight attendant did make sure my personal item was carefully stored under the seat in front of me. I was made to feel welcome as a customer as I made my first trip with a few disabilities. Entertainment and wifi worked quite well. The only food service were snacks and drinks. Those were okay. Overall it was a very smooth flight and encouraged me to use Delta again.

Only one side of the heafphone jack work. Crew was friendly and helpful.

Typical flying experience in the US. Nothing particularly good or bad.

Airline lost my luggage and set me back a day worth of travel due to having to stay in Denver to wait on my luggage

Great - This was the last flight before hurricane closures and did a quick turnaround to get the plane heading north. Much appreciated.

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Flight was on time arrived at the destination 10min early they kept in touch via email

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

Did not enjoy this flight at all. All of my coworkers flew delta and I chose JetBlue because I really value how simple the WiFi and entertainment is and this flight I didn’t get either. Crew staff was unsympathetic to my system not working, everyone I asked for help with was extremely bothered by my request for help.

In flight on demand didn't work at our seats. Only a single beverage/snack run.

Little snafu at boarding. Staff communicated with gate poorly. Flight attendant was rude making disembark early. This was an older mint class. Needs an overhaul for sure. Food was good. The male flight attendant was really nice.

My encounter with the entertainment services provided on board was moderate; the functionality of the Wi-Fi connection was either sluggish or nonoperational, while the display screens were antiquated and suffered from poor visibility. On the positive side, the cabin exuded a sense of expansiveness, and the crew exhibited amiable and accommodating behavior throughout the journey.

Everything was great except for some reason crew and ground crew could not figure out how to deal with an electric wheelchair and it delayed us 20-30mins. Was pretty frustrating for passengers and the captain.

Booked a united Air flight with option to pick seat , then found out was on an Air Canada flight with assigned seat , then they wanted a several dollar charge for some 25 cent value entertainment listening ear device

Poor and identical to the first two legs, except for the crew who were patient, professional and of pleasant and jovial disposition!

This was a 5 hour flight with no entertainment and with a snack being provided (pretzels and fruit bar), which are both high in carbs and sugar. Nuts would have been a better choice.

Late out of the gate, late to takeoff. No screens on plane. Uncomfortable window seat.

We were delayed because of ground crew, not because the plane wasn’t ready to go. The food was better than usual!

The plane was so gross and dirty. Literally saw dust layering and flowing out the grey vents. Dust was all over the air vent knobs to the point where I took my sani wipe and cleaned them down so at least it wasn't blowing my my face. Also, I upgraded and paid for Wifi and it's always so spotty. I get we are in the air, but don't charge for it if it's not going to work. I expect so much more from United. They really are giving up.

Liked that we left on time for each flight. Snacks not the best, but we're okay.

Never nice, United Express partners always do an amazing job.

It was fine. The flight attendant appeared to be in a bad mood but everything was fine.

A three (3) hour flight should have meal service in First Class, not just potato chips!

They could have done a better job announcing the boarding groups and asked for more drinks (water) if needed.

No explanation of why there was no snack and drink service (unless requested) when there was service in the other direction.

It was exactly what I expected, actually arriving sooner than scheduled.

One of the reasons I fly American is because the seating is more comfortable than most airlines. Even in the back of the plane.

Everything was ok except that we had to de-ice the plane which took about 20 mins. I realize this is a safety issue, but it caused us to miss a connection in Charlotte by 15 mins which meant a four hour layover. I think the thing that bothered me was American Airlines knew we were only 15 mins late, so couldn’t they have waited for us? There were about 10 of us that had to take alternate planes. I remember recently waiting 15 to 20 mins for passengers connecting with flights we were on. Just wondering why they couldn’t do the same for ours.

Crazy seating issues. We got seated far apart. Offered middle seats at a premium rate. Why is a middle seat now the expensive seat? Baffling.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

Overall boarding and debarking is a joke. I dont even bring luggage anymore on trips because you can never allow them to be place then in the overhead bin or you have to pay or you check them which is even worse having to wait for your luggage on the tarmac.

RE Food: Wish there was a choice for No Rating. Flew from Honolulu to Los Angeles on a Red-Eye flight (11:00 pm to 7:30 am). Other than a package of cookies with a beverage choice offered soon after take-off, and a beverage choice shortly before landing, no other food choices were offered. Everyone slept or rested for most of the trip. Nothing to rate. RE Entertainment: Everyone was sleeping most of the flight. Only saw one passenger watch about 30 minutes of entertainment on his iPad. I never attempted to access any entertainment options.

Very confining seats side to side. Not wide enough for any comfort.

the seats are the hardest I've ever felt; narrower and less leg space and I am small. I could have bid on a comfier seat but the price would have ended up closer to an economy plus seat on a more reliable airline. Only used this airline because of the timing and non-stop. I was afraid from the get-go I wouldn't get there. Apparently, I was lucky

Seamless boarding process, flight was early, crew and passengers nice. Crew was professional as well. Seats are super thing but reasonably comfortable for a 2-3 hrs flight. No on board entertainment, except maybe for paid internet. No water, no snacks. I feel all airlines should offer free water. I didn’t care paying for it, however water is free everywhere in the US and it almost like a basic human right in a civilized society.

Fantastic. Had handicapped traveler and they helped us through security, helped with boarding, helped put wheelchair together, and were all very patient. A pleasant change from previous spirit flights I’ve taken. Highly recommend.

Really nice, flight attendants were so helpful with me and my kids. Extremely grateful, keep up the good work and spirit :)

They lost my luggage on a direct non-stop flight.

I liked the low price. I did not like the cramped passenger seats. As a below average size person I was cramped in the seat; I can only imagine how uncomfortable an average or large size person would be. I guess that is part of the deal with low cost airlines.

Very clean and new airplane. The internet purchase was not worth the money requested

LA to Seattle was a smooth process. Seattle to LA was delayed more Than 6hrs

Spirit's seating does not work for an overnight flight and my back is killing me. This airline does not meet the minimum standards for being an airline.

I could not print my boarding passes and had to see an agent. However, the agents were very friendly and helpful.

Book Cheap Caribbean Islands Plane Tickets

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Caribbean Islands found on KAYAK in the last 72 hours.
11/18Mon
nonstopFrontier
3h 59mBOS-SJU
11/18Mon
1 stopFrontier
21h 37mSJU-BOS
$102
11/18Mon
1 stopFrontier
17h 49mBOS-SJU
11/19Tue
1 stopFrontier
21h 36mSJU-BOS
$105
11/17Sun
nonstopJetBlue
4h 06mBOS-SJU
11/24Sun
nonstopJetBlue
4h 10mSJU-BOS
$194
11/19Tue
nonstopDelta
4h 05mBOS-SJU
12/5Thu
nonstopDelta
4h 22mSJU-BOS
$203
1/5Sun
nonstopJetBlue
3h 58mBOS-SJU
1/14Tue
1 stopJetBlue
7h 15mSJU-BOS
$219
11/3Sun
nonstopDelta
4h 12mBOS-SJU
11/8Fri
nonstopDelta
4h 13mSJU-BOS
$233
1/21Tue
1 stopUnited Airlines
6h 02mPHL-SJU
2/5Wed
2 stopsUnited Airlines
13h 19mSJU-PHL
$264
11/11Mon
1 stopUnited Airlines
6h 17mEWR-SJU
11/13Wed
nonstopUnited Airlines
4h 17mSJU-EWR
$268
1/20Mon
1 stopAmerican Airlines
6h 00mIAD-SJU
1/23Thu
1 stopAmerican Airlines
6h 15mSJU-IAD
$350
10/29Tue
1 stopAmerican Airlines
7h 50mJFK-SDQ
11/6Wed
1 stopAmerican Airlines
8h 56mSDQ-JFK
$360

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Caribbean Islands found on KAYAK in the last 72 hours.
11/10Sun
nonstopFrontier
3h 59mBOS-SJU
$44
1/13Mon
1 stopFrontier
9h 01mBOS-SJU
$51
11/23Sat
nonstopJetBlue
3h 53mBOS-SJU
$93
1/1Wed
1 stopJetBlue
8h 06mJFK-SJU
$109
11/20Wed
nonstopDelta
4h 05mBOS-SJU
$112
11/21Thu
1 stopAmerican Airlines
16h 04mJFK-SJU
$121
10/30Wed
nonstopDelta
4h 12mBOS-SJU
$132
11/20Wed
2 stopsAmerican Airlines
11h 53mJFK-SJU
$146
12/11Wed
1 stopUnited Airlines
7h 40mIAD-SJU
$161
11/19Tue
2 stopsUnited Airlines
14h 06mBOS-SJU
$161

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Last minute flights to Caribbean Islands

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Caribbean Islands that are departing in the next 10 days.
10/27Sun
nonstopFrontier
3h 49mPHL-SJU
12/10Tue
multi-stopFrontier
15h 33mSJU-PHL
$150
10/26Sat
multi-stopSpirit Airlines
11h 33mPHL-SJU
11/1Fri
nonstopSpirit Airlines
4h 07mSJU-PHL
$151
10/27Sun
nonstopDelta
4h 12mBOS-SJU
10/29Tue
nonstopDelta
4h 13mSJU-BOS
$243
10/27Sun
multi-stopUnited Airlines
6h 32mBOS-SJU
11/1Fri
multi-stopUnited Airlines
9h 06mSJU-BOS
$252
10/27Sun
nonstopJetBlue
4h 02mBOS-SJU
11/5Tue
nonstopJetBlue
4h 09mSJU-BOS
$263
10/26Sat
nonstopDelta
4h 12mBOS-SJU
10/31Thu
nonstopDelta
4h 17mSJU-BOS
$273
10/27Sun
multi-stopUnited Airlines
6h 32mBOS-SJU
10/31Thu
multi-stopUnited Airlines
9h 41mSJU-BOS
$282
10/27Sun
nonstopJetBlue
4h 02mBOS-SJU
10/29Tue
nonstopJetBlue
4h 11mSJU-BOS
$283
10/27Sun
multi-stopAmerican Airlines
7h 00mJFK-SJU
10/29Tue
multi-stopAmerican Airlines
6h 42mSJU-JFK
$311
10/26Sat
multi-stopAmerican Airlines
7h 30mJFK-SJU
11/2Sat
multi-stopAmerican Airlines
7h 13mSJU-JFK
$312

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Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to Caribbean Islands
Cabin classes available on flights to Caribbean Islands. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.