$77 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 9/25. 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
1 adult, Economy

KAYAK searches 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
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Flight Deals

Cheap Flights to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$206
Santo Domingo
Santo Domingononstop$199
Montego Bay
Montego Baynonstop$211
Nassau
Nassaunonstop$251
Kingston
Kingstonnonstop$241
Providenciales
Providencialesnonstop$319
Port of Spain
Port of Spainnonstop$282
Bridgetown
Bridgetown1 stop$320
Willemstad
Willemstad1 stop$253
St. John's
St. John'snonstop$334
Puerto Plata
Puerto Platanonstop$320
Aguadilla
Aguadillanonstop$122
Punta Cana
Punta Cananonstop$206
Santo Domingo
Santo Domingononstop$199
Montego Bay
Montego Baynonstop$211
Nassau
Nassaunonstop$251
Kingston
Kingstonnonstop$241
Providenciales
Providencialesnonstop$319
Port of Spain
Port of Spainnonstop$282
Bridgetown
Bridgetown1 stop$320
Willemstad
Willemstad1 stop$253
St. John's
St. John'snonstop$334
Puerto Plata
Puerto Platanonstop$320
Aguadilla
Aguadillanonstop$122

Book Cheap Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Caribbean Islands

Fri, Oct 24 - Wed, Oct 29
Frontier Logo
11:30 am - 3:24 pmJFK-SJU
3h 54mnonstop
Frontier Logo
9:00 am - 1:03 pmSJU-JFK
4h 03mnonstop
$132Frontier
Find Deal
Wed, Sep 24 - Wed, Sep 24
Frontier Logo
6:00 am - 9:56 amJFK-SJU
3h 56mnonstop
Frontier Logo
9:26 pm - 1:25 amSJU-JFK
3h 59mnonstop
$133Frontier
Find Deal
Sun, Sep 28 - Sat, Oct 4
JetBlue Logo
6:15 am - 10:10 amEWR-SJU
3h 55mnonstop
JetBlue Logo
5:00 pm - 9:04 pmSJU-EWR
4h 04mnonstop
$167JetBlue
Find Deal
Tue, Oct 7 - Mon, Oct 13
JetBlue Logo
5:25 pm - 9:24 pmJFK-SJU
3h 59mnonstop
JetBlue Logo
3:03 am - 7:00 amSJU-JFK
3h 57mnonstop
$170JetBlue
Find Deal
Tue, Oct 14 - Wed, Oct 22
United Airlines Logo
6:00 am - 12:34 pmLGA-SJU
6h 34m1 stop
United Airlines Logo
4:55 pm - 11:43 pmSJU-LGA
6h 48m1 stop
$211United Airlines
Find Deal
Wed, Oct 1 - Fri, Oct 31
United Airlines Logo
9:55 am - 8:38 pmLGA-SJU
10h 43m1 stop
United Airlines Logo
4:50 pm - 11:30 pmSJU-LGA
6h 40m1 stop
$214United Airlines
Find Deal
Tue, Oct 21 - Tue, Nov 4
American Airlines Logo
11:00 am - 10:10 pmLGA-SJU
11h 10m1 stop
American Airlines Logo
7:15 am - 4:01 pmSJU-LGA
9h 46m1 stop
$215American Airlines
Find Deal
Wed, Oct 22 - Wed, Oct 29
American Airlines Logo
6:00 am - 3:55 pmLGA-SJU
9h 55m1 stop
American Airlines Logo
2:35 pm - 11:45 pmSJU-LGA
9h 10m1 stop
$235American Airlines
Find Deal
Mon, Dec 8 - Wed, Dec 10
Delta Logo
6:00 am - 2:10 pmIAD-SJU
7h 10m1 stop
Delta Logo
7:00 am - 5:01 pmSJU-IAD
11h 01m1 stop
$245Delta
Find Deal
Wed, Oct 29 - Tue, Nov 4
Delta Logo
8:30 am - 12:28 pmJFK-PUJ
3h 58mnonstop
Delta Logo
2:53 pm - 5:59 pmPUJ-JFK
4h 06mnonstop
$282Delta
Find Deal
Booking Insights

KAYAK's insights & trends for flights to Caribbean Islands

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

What is the cheapest flight to Caribbean Islands?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

The cheapest ticket to Caribbean Islands from the United States found in the last 72 hours was to Nassau, at $89 round-trip. The most popular route is Atlanta (ATL) to San Juan Luis Munoz Marin Intl Airport (SJU) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $106.

How much is a flight to Caribbean Islands?

The average and cheapest price for all round-trip flights to Caribbean Islands from each origin found by users searching on KAYAK in the last month.

A flight to Caribbean Islands costs $376 on average. The cheapest price found on KAYAK in the last 2 weeks was $53 for the route New Haven (HVN) to San Juan Luis Munoz Marin Intl Airport (SJU). The most popular routes on KAYAK are Orlando to Oranjestad which costs $405 on average, and New York to Oranjestad, which costs $455 on average.

See prices from:

What is the cheapest month to fly from the United States to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from the United States to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from the United States to Caribbean Islands is February, when tickets cost $291 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $475 and $452 respectively.

How far in advance should I book a flight from the United States to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from the United States to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Which is the cheapest airport to fly into in Caribbean Islands?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Caribbean Islands is Ponce Mercedita Airport (PSE), with an average flight price of $126.

Good to know

Low seasonSeptember
Cheapest flight$77
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Newark Liberty Airport to San Juan Airport

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

Insights shared by verified travelers who flew to Caribbean Islands 
Verified travelerFlew with FrontierRDU-SJUMay 2025
If you are in the first group to board, stay standing early next to the gate entrance so you really enter first. Otherwise you end up entering all groups at the same time and will loose your carry on space over your seat.
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.
Maria AlejandraFlew with FrontierJFK-SJUAug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix
Verified travelerFlew with Spirit AirlinesFLL-KINApr 2024
Check in very early Eat a complete meal before flying Don't be overweight
Verified travelerFlew with United AirlinesEWR-SDQApr 2024
Early check in online, get on time for the flight
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.
NicoleFlew with Spirit AirlinesTPA-SJUFeb 2024
Follow the rules on the backpack and will not have any trouble, the payment for the bag at the gate is $99 almost the price of the ticket, is not worth it.
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.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from the United States 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 the United States to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from the United States 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 the United States 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 the United States 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 the United States 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 the United States to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Caribbean Islands?

    Based on KAYAK data, the cheapest day to fly to Caribbean Islands is Tuesday where round-trip tickets can be as cheap as $469. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $532 on average.

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

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $388 on average. Morning departures are around 100% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $481.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for cheap airfare to Caribbean Islands? 25% of our users found round-trip tickets to Caribbean Islands for the following prices or less: From Miami $303, from Newark $550, from Chicago O'Hare Intl $623
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Caribbean Islands flight deals.

Reviews of the 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.
7.9
DeltaOverall score based on 7957 reviews
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
8.2Boarding
Airline reviews

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

8.0 ExcellentTarun, Sep 2025MCO - LHR
Read more Delta reviews

Passengers need to check in big baggage instead of bringing on the plane. That cause inconvenience for everyone. Otherwise flight was good.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

We had to deboard 2 times due to maintenance issues. They changed the plane, and then we got deviated to LAX due to maibtenance issues on the other plane, had to sleep at LAX and los a full day.

Everything was good, except the seats in economy were so close together, you could barely get out when the seat in front of your was reclined. If the airlines keep jamming in more and more seats, it will become intolerable. I will look for another airline that considers customer comfort and does not keep adding more rows of seats for more profit.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

IAD with the archaic people movers is just a place to be avoided.

Great service on board. Boarding a bit slow due to process. Food was pretty average.

Tastless food and too obvious lack of enthusiasm for service in the economy vesus business class

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Spirit rescheduled a 4:30 PM flight to 8:52 AM. That's ridiculous and borderline fraud.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The terminal crew is so rude cabin crew is extremely rude flight is very good

Spirit is low fare air line. Food also cost you. No free food.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

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.

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