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$41 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 10/8. 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
0 bags
Sat 8/17
Sat 8/24

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Best Caribbean Islands Flight Deals

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

Punta Cana
Punta Cana1 stop$161
Montego Bay
Montego Bay1 stop$223
Santo Domingo
Santo Domingo1 stop$167
Oranjestad
Oranjestadnonstop$222
Nassau
Nassaunonstop$238
Kingston
Kingstonnonstop$277
Simpson Bay
Simpson Bay1 stop$181
Providenciales
Providencialesnonstop$308
Bridgetown
Bridgetown1 stop$173
Port of Spain
Port of Spain1 stop$143
George Town
George Townnonstop$300
Willemstad
Willemstad1 stop$325
Aguadilla
Aguadillanonstop$111
St. John's
St. John's2 stops$312

Good to know

Low season

September

High season

December

Cheapest flight

$41
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 Newark Liberty Airport 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 51m, covering a distance of 1532 miles. The most popular route is New York - San Juan with an average flight time of 3h 44m.

  • 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 $75. 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 $156.

  • Which airlines fly to Caribbean Islands?

    JetBlue, Qatar Airways & Delta fly the most frequently from the United States to Caribbean Islands. The most popular route is from New York to San Juan, and Qatar Airways, JetBlue 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 (15% of total searches to Caribbean Islands). The next most popular destinations are Santo Domingo (12%) and Montego Bay (11%). 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.

Top 5 airlines flying to Caribbean Islands

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 9762 reviews
8.6Crew
8.2Boarding
7.4Food
7.9Comfort
8.0Entertainment
Airline reviews

Flight was delayed. Had to get rebooked. Diamond medallion but stuck in a crappy seat. Rebooked flight then got delayed again. Then when we finally boarded, we waited another hour for a new crew. Then landed in JFK and sat for another 40 minutes waiting for a crew to come to the gate to be able to deplane. Hot mess all around, which unfortunately is becoming the norm for Delta

2.0 MediocreDan, Jul 2024AUS - JFK
Read more about Delta reviews

Flight was delayed. Had to get rebooked. Diamond medallion but stuck in a crappy seat. Rebooked flight then got delayed again. Then when we finally boarded, we waited another hour for a new crew. Then landed in JFK and sat for another 40 minutes waiting for a crew to come to the gate to be able to deplane. Hot mess all around, which unfortunately is becoming the norm for Delta

It was terrible! Two hour delays, poor in flight service, made us check our carry on even though there was plenty of overhead storage

Terrible flight Delayed for over an hour without a reason Told all over head storage was full. It was not. Made to check our bags. What a terrible experience. Fly American.

Older plane and it came with Fleas and flea bites!

My seat was moved closer to the front of the cabin since I had requested wheelchair assistance to the gate.

Rough day of travel all the way around. Wrong info given to us multiple times and mistakes in their booking making our trip 10 hours longer than planned. I’m bummed because I fly Delta all the time and love them. Mistakes happen. Just bummed that this was a rare trip our whole family was traveling together.

Still room for improvement in food and beverage selection: bring back Cognac

Flight was canceled so it was not a great experience. Boarded, then deboarded. Delayed, boarded a new plane then deboarded the 2nd plane and flight was canceled. Then booked a fight to Rome and took a train to Venice the next day. Lost an entire day +

My seat was changed at the last minute and I was moved to the last row, right next to the bathroom despite selecting my seat well in advance. I was also made to check my carry on due to space but when I got on the plane there was significant empty overhead space. Picking up my carry on from the luggage carousel added time to my trip which had already been extended due to delay.

All good on Delta's part. Passengers could be a little more courteous to each other.

Over 2 hour delay for a 50-minute flight is unacceptable, especially in normal weather. Very poor communication via app

In-flight staff was very helpful and excellent. However, the flight was delayed by 90 minutes. Also the boarding process should be expedited in case of delayed flights. This will help the passengers trying to make international connections.

They delayed our flight by 45 minutes and then re-updated the departure time back to normal schedule with no notification, email, or app update causing probably 40 people to miss the flight as they left without us.

Kayak sent over to jet blue my account being Mike Callaghan instead of Michael. I have a jet blue account with Michael that was connected

Som delays but overall we almost made it on the original time.

terrible. Because I felt very unwell during the flight. How do they leave a woman alone in the middle of 2 men? an obese man who was falling on top of me.

They put me on a chair in between two men, one overweight who was almost falling on top of me, and the other was even uncomfortable because I was half falling because of what the other was pushing me. I stayed with. my feet were swollen from fluid retention and from being unable to accommodate myself. it was very uncomfortable. I asked for help but they told me that the flight was full and they couldn't help me. I got off the plane almost unable to walk due to the inflammation. and then at FLL airport I asked for help because I couldn't go to my next flight, which was a connection.

The walk from baggage claim to the taxi is very difficult for older people I will never fly into JFK again. It is physically challenging

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

Lufthansa placed a 300 lb passenger in the aisle seat and I was stuck in the middle leaning sideways with no arm rest or ability to sit up straight and fully use my seat (due to encroachment-the seats are very narrow) the entire flight.

My flight was delayed for a whole day, so I lost a day of my vacation.

I was refused to used the toilet closes to my seat and had to go to the back of the plane .. it was difficult for me I’m a wheelchair customer

East Lounge in Denver was terrible. Turning away active military on orders? Really? Sad.

Miserable. Active military on orders turned away from Lounge because not in uniform. This is completely contrary to United’s online lounge access policy. Sad that employees aren’t trained better. This is not the United Airlines my parents used to regularly fly with.

Was a good flight , well served by the flight attendants. Boarding went smoothly, flight was smooth.

Too many canceled flights and kept my wife and I separated on alternate flights. We did not fly out of Denver. We paid a lot of money for the seats we wanted and now that money is gone and we did not sit together. That being said, the many agents were very friendly and did everything possible to help us.

Terrible Initial delay for almost an hour before boarding and departing in Seattle. Then a “customary” wait on the tarmac in Newark after landing for half an hour. I call it customary because it happens almost every time I land in Newark. I do t know if it’s Newark or United airline but it’s a travesty . I use Newark because it’s closer than jfk to where I live but am strongly considering switching because of extremely poor in time performance and Condé and delay after landing

Everything could’ve been better. The boarding process was a little tedious, and then they put me in a seat with the window did not open, which gave me a very uncomfortable feeling considering I had told them that. The entertainment system didn’t work for quite some time and because I had to heavily medicate myself to not have a panic attack I missed dinner and barely ate anything on the flight. Not to mention the religious man next to me, praying mostly and humming the whole flight.

The boarding process was delayed and the miscommunication of what seats are broken

Great flight. The captain did a great job of minimizing some minor turbulence and in general it was a smooth flight. Early departure and early arrival at destination. Great service.

It was the worst experience ever. Cabin temperature cold, for which they did not have any blankets upon my asking. We paid $125 extra for each passenger to get extra space sits; the sits were ridiculously small, tight, and uncomfortable! The flight attendant dropped ice on me and my sister! All in all, American Airlines deserves below zero!

Our flight left on time and we arrived a few minutes early. Great service!

It was the coldest flight I have ever been on

My morning PHX to NY flight was canceled. Not a cloud in the sky. No wind. No weather across the country. My guess is they canceled the flight because they didn’t have enough people or a mechanical issue. Either way really bad. I checked it at midnight and the 830a flight was on time so I was very surprised when I woke up to see the flight canceled and I’ve been rebooked on a flight… An hour earlier than my originally scheduled one. Of course I missed this earlier flight because AA texted at 4 AM when I was sleeping. I was re routed to Miami, boarded a plane, sat in the heat for 40 minutes, then boarded because of mechanical issues and had to wait another hour before finally getting to New York Ironically, the 430 Phoenix to New York flight landed at the same time I did… I could’ve been sitting at the pool all day vs jumping through hoops. never ever will I again fly American Airlines. No offer of a free drink, maybe a few points on my advantage account nothing… As if nothing happened and they did not inconvenienced me at all. I’m so sick of the dumb crackers that they give us on these flights. It’s really like a budget Airlines these days. A far fall for s once mighty company.

I got food poisoning - lasted 4 days after starting medications - someone should check with food delivery.

I like the speed of boarding and deplaning and the fact that everything was on time. The crew (attendants) were probably quite new and did not begin the in cabin service until 30 min before landing even though there was little to no air turbulence for the last 1.5 hours of the flight. It made for a mad scramble at the end to get trash collected and carts stowed before touch down.

Our 9:10 am scheduled flight continued to get delayed all day with no information given from the agents as to why. It wasn’t until I went to the customer service desk and got us switched to another flight at 2:44 pm (that wasn’t nonstop like our booked flight) that the agent finally was able to find out it was due to a fuel leak. I don’t know if our original flight ever took off but I don’t find it acceptable to leave people sitting in an airport all day with no explanation.

Horrible airline! They always got something messed up with their planes. 3 hour delayed made us missed both out flights. Had to wake up early in the morning next morning to get another flight!

If there was enough room for me to bring my carry on luggage with me on the flight.

At LAS airport, bag drop process was hard, you need to pay for a faster drop. There was a long line for a free drop and you need to do it by yourself. No one helped you. Bad experience at LAS airport.

Didn’t board the flight asked for a flight credit for future flights wasn’t given it. One of the children were to scared to board the flight

You get what you pay for, but those tickets weren't cheap, so I expected better, but Spirit is just one of those airlines.

The worse experience ever from flight delays customer service and professionalism.

Spirit's website on mobile did not work. Check-in kiosk would not allow us to check in at 12:09 for a 12:52 departure. Went to front desk, they said we had missed our flight and there was nothing they could do, would not offer a refund, and we're extremely rude and condescending. They said if we had checked in at 12:07 they could have given us our boarding pass. We spent $650 to take a different flight on Southwestern. When we got to the gate and sat down at 12:25, Spirit had delayed their departure time for our original flight to 1:54. I've never been more irritated while flying. I will never book another flight through Spirit again.

We were delayed departing and also it took 40 min before we were able to exit the plane after landing and there was no AC I felt like I’m going to die

My flight was cancelled an hour before take off time.

They charge you for everything. Even water. They accepted my dog as a service dog in my reservation. Then they asked for a DOT form that was impossible to provide. I had to pay $175 for my service to fly with me, that would protect me from death if I ate peanuts. They did not however, serve peanuts on the plane.

Everything was on time. Several passengers were rude/impatient when deplaneing at both FLL and PNS - but this is our society today w/ no common courtesy.

Checking one bag in after we already got our boarding passes and tag for the bag was ridiculous. Only two agents working the counter. It took forever! Second, the all male flight attendant staff was rude by yelling at those of us on the plane, being short with flyers, and speaking so fast that it was hard to understand what they were saying.

Book Cheap Caribbean Islands Plane Tickets

Recent round-trip flight deals

9/10Tue
nonstopFrontier
4h 25mEWR-SJU
9/18Wed
nonstopFrontier
4h 25mSJU-EWR
$96
9/21Sat
nonstopFrontier
4h 05mEWR-SJU
9/25Wed
nonstopFrontier
4h 08mSJU-EWR
$100
9/11Wed
2 stopsAmerican Airlines
8h 59mJFK-SJU
9/16Mon
1 stopAmerican Airlines
17h 39mSJU-JFK
$234
9/25Wed
1 stopAmerican Airlines
8h 35mJFK-SJU
10/1Tue
1 stopAmerican Airlines
6h 39mSJU-JFK
$239
9/11Wed
1 stopJetBlue
6h 42mJFK-SJU
9/25Wed
1 stopJetBlue
8h 00mSJU-JFK
$244
8/21Wed
1 stopJetBlue
8h 19mJFK-SJU
8/23Fri
1 stopJetBlue
9h 40mSJU-JFK
$248
12/13Fri
nonstopDelta
4h 04mJFK-SJU
12/15Sun
nonstopDelta
4h 04mSJU-JFK
$283
9/7Sat
nonstopDelta
4h 04mJFK-STI
9/16Mon
nonstopDelta
3h 45mSTI-JFK
$296
8/31Sat
1 stopUnited Airlines
10h 15mEWR-AUA
9/5Thu
nonstopUnited Airlines
4h 54mAUA-EWR
$318
9/6Fri
1 stopUnited Airlines
18h 10mEWR-AUA
9/13Fri
nonstopUnited Airlines
4h 54mAUA-EWR
$398

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Recent one-way flight deals

10/8Tue
nonstopFrontier
4h 05mEWR-SJU
$41
8/20Tue
nonstopFrontier
4h 23mEWR-SJU
$47
10/6Sun
1 stopAmerican Airlines
15h 03mMCO-SJU
$92
9/4Wed
1 stopJetBlue
9h 08mJFK-SJU
$112
9/17Tue
2 stopsAmerican Airlines
8h 59mJFK-SJU
$117
9/1Sun
nonstopJetBlue
4h 45mEWR-AUA
$119
9/16Mon
nonstopDelta
4h 04mJFK-PUJ
$141
11/25Mon
nonstopDelta
4h 04mJFK-SJU
$142
7/29Mon
nonstopUnited Airlines
4h 46mEWR-AUA
$169
10/27Sun
1 stopUnited Airlines
6h 35mEWR-AUA
$173

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Last minute flights to Caribbean Islands

Last minute flight, train and bus deals

7/20Sat
nonstop
2h 58mMCO-SJU
7/31Wed
multi-stop
9h 54mSJU-MCO
$168
7/23Tue
nonstopFrontier
3h 54mJFK-SJU
8/24Sat
nonstopFrontier
4h 27mSJU-JFK
$171
7/20Sat
multi-stopAmerican Airlines
15h 11mJFK-SJU
7/27Sat
multi-stopAmerican Airlines
16h 35mSJU-JFK
$311
7/22Mon
multi-stopAmerican Airlines
14h 47mLGA-SJU
7/29Mon
multi-stopAmerican Airlines
15h 30mSJU-LGA
$311
7/18Thu
nonstopUnited Airlines
4h 46mEWR-AUA
7/22Mon
nonstopUnited Airlines
5h 02mAUA-EWR
$314
7/23Tue
nonstopJetBlue
4h 01mJFK-SJU
8/3Sat
multi-stopJetBlue
6h 47mSJU-JFK
$316
7/18Thu
multi-stopUnited Airlines
6h 25mEWR-AUA
7/22Mon
nonstopUnited Airlines
5h 02mAUA-EWR
$318
7/19Fri
nonstopJetBlue
3h 02mMCO-SJU
7/22Mon
nonstopJetBlue
3h 09mSJU-MCO
$339
7/20Sat
nonstopDelta
4h 20mJFK-SJU
11/30Sat
nonstopDelta
4h 04mSJU-JFK
$399
7/22Mon
nonstopDelta
4h 20mJFK-SJU
7/23Tue
nonstopDelta
3h 54mSJU-JFK
$438

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Flights to Caribbean Islands

Return flight deals:

Caribbean Islands - United States

Cabin classes:

$94
$83
$49
$24

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