$75 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 5/25. 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, 0 bags

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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 Cana1 stop$252
Santo Domingo
Santo Domingononstop$239
Montego Bay
Montego Bay1 stop$263
Nassau
Nassaunonstop$258
Kingston
Kingstonnonstop$324
Providenciales
Providencialesnonstop$382
Port of Spain
Port of Spainnonstop$287
Bridgetown
Bridgetown1 stop$296
Willemstad
Willemstad2 stops$277
Aguadilla
Aguadillanonstop$182
Puerto Plata
Puerto Plata1 stop$322
St. John's
St. John'snonstop$434
Punta Cana
Punta Cana1 stop$252
Santo Domingo
Santo Domingononstop$239
Montego Bay
Montego Bay1 stop$263
Nassau
Nassaunonstop$258
Kingston
Kingstonnonstop$324
Providenciales
Providencialesnonstop$382
Port of Spain
Port of Spainnonstop$287
Bridgetown
Bridgetown1 stop$296
Willemstad
Willemstad2 stops$277
Aguadilla
Aguadillanonstop$182
Puerto Plata
Puerto Plata1 stop$322
St. John's
St. John'snonstop$434

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

週二, 5月 12 - 週四, 5月 14
Frontier Logo
11:20 pm - 2:08 am
MCO
-
SJU
2h 48mnonstop
Frontier Logo
5:15 pm - 6:40 am
SJU
-
MCO
13h 25m
1 stop
$166Frontier
週一, 5月 11 - 週三, 5月 13
Frontier Logo
7:52 pm - 10:43 pm
MCO
-
SJU
2h 51mnonstop
Frontier Logo
7:30 am - 9:53 pm
SJU
-
MCO
14h 23m
1 stop
$167Frontier
週三, 5月 27 - 週四, 6月 4
Spirit Airlines Logo
6:42 pm - 10:42 pm
EWR
-
SJU
4h 00mnonstop
Spirit Airlines Logo
7:30 am - 11:43 am
SJU
-
EWR
4h 13mnonstop
$215Spirit Airlines
週日, 5月 24 - 週四, 5月 28
Spirit Airlines Logo
6:42 pm - 10:42 pm
EWR
-
SJU
4h 00mnonstop
Spirit Airlines Logo
8:04 pm - 9:04 am
SJU
-
EWR
13h 00m
1 stop
$216Spirit Airlines
週一, 8月 17 - 週三, 8月 19
American Airlines Logo
8:00 am - 11:59 pm
JFK
-
SJU
15h 59m
1 stop
American Airlines Logo
10:33 am - 9:30 pm
SJU
-
JFK
10h 57m
1 stop
$266American Airlines
週二, 6月 9 - 週三, 6月 17
JetBlue Logo
1:50 pm - 5:51 pm
JFK
-
SJU
4h 01mnonstop
JetBlue Logo
5:07 am - 9:00 am
SJU
-
JFK
3h 53mnonstop
$267JetBlue
週二, 7月 14 - 週二, 7月 21
JetBlue Logo
8:00 pm - 12:10 am
JFK
-
SJU
4h 10mnonstop
JetBlue Logo
1:30 pm - 5:23 pm
SJU
-
JFK
3h 53mnonstop
$268JetBlue
週三, 8月 19 - 週三, 8月 26
American Airlines Logo
6:30 am - 4:03 pm
JFK
-
SJU
9h 33m
2 stops
American Airlines Logo
7:14 pm - 9:14 am
SJU
-
JFK
14h 00m
1 stop
$271American Airlines
週六, 7月 4 - 週三, 7月 8
Delta Logo
7:25 pm - 11:43 pm
JFK
-
SJU
4h 18mnonstop
Delta Logo
1:10 pm - 5:19 pm
SJU
-
JFK
4h 09mnonstop
$277Delta
週四, 5月 14 - 週四, 5月 28
Delta Logo
9:00 pm - 12:59 am
JFK
-
STI
3h 59mnonstop
Delta Logo
6:00 am - 9:45 am
STI
-
JFK
3h 45mnonstop
$417Delta
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 San Juan Luis Munoz Marin Intl Airport, at $124 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 $124.

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 $403 on average. The cheapest price found on KAYAK in the last 2 weeks was $56 for the route Fort Lauderdale (FLL) to Oranjestad (AUA). The most popular routes on KAYAK are Orlando to Oranjestad which costs $477 on average, and Philadelphia to Oranjestad, which costs $616 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 October, when tickets cost $250 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $442 and $340 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 2 weeks before departure, which saves you about 8% compared to booking last minute. 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 Georgetown Exuma Intl Airport (GGT), with an average flight price of $162.

Good to know

Low seasonSeptember
Cheapest flight$75
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Philadelphia 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 
SteveFlew with Spirit Airlines
FLL
-
STI
Apr 2026
Earlier is better for accuracy. Later is better to avoid crowds
Verified travelerFlew with JetBlue
MCO
-
SJU
Dec 2025
Always arrive at your schedule, no matter if say that the flight is delay. Orlando Airport most of the time have a lot of passenger and is better to be on time just in case
SephanyahFlew with Caribbean Airlines
FLL
-
POS
Nov 2025
Reach on time for you check-in or use web check-in.
Verified travelerFlew with Frontier
RDU
-
SJU
May 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 Airlines
IAH
-
SJU
Sep 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 Frontier
JFK
-
SJU
Aug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix
Verified travelerFlew with Spirit Airlines
FLL
-
KIN
Apr 2024
Check in very early Eat a complete meal before flying Don't be overweight
Verified travelerFlew with United Airlines
EWR
-
SDQ
Apr 2024
Early check in online, get on time for the flight
KarenFlew with Spirit Airlines
FLL
-
SJU
Jan 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 Airlines
TPA
-
SJU
Feb 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 Airlines
IAH
-
POS
Dec 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 $430. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $478 on average.

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 $315, from Newark $499, from Chicago O'Hare Intl $578
  • 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 8463 reviews
8.1Boarding
7.2Food
8.5Crew
7.9Comfort
7.8Entertainment
Airline reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

6.0 GoodSilvestre, Apr 2026
MCO - GRU
Read more Delta reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

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.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Some crew were unfriendly or in some cases just straight up rude.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

United Airline crews were very friendly and very attentive. 12 hours flight was gone like in a shorter one.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

Food was surprisingly delicious. Space in the seat is horrible when the seating front is reclined. Movie offerings were terrible. Crew was friendly and helpful.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

Not having an assigned seat until boarding and then having to check my bag.

Flight emergency landed in Chicago due to “Odor” in back of plane . Had to buy ANOTHER TICKET to get to Boston cash out of my own pocket . Then they would notchange my return flight time without a 400. Charge!!!! Insulting.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Flight was as expected. But it was delayed an hour. Also, my luggage got damaged. So that sucked especially since the damage made navigating the airport difficult. Walking to get ground transportation is sooo far away now and my checked bag was difficult to carry.

we were an hour delayed after boarding and given no reason. Headsets cost money. Also there were openrows with no one setting in them but we were told we were not allowed to swtich.

Crew was very friendly. Did not like being jammed in the back middle seat. Don’t understand why I can not select an aisle for free based on first come first serve. Also first time I’ve been on a flight which attempted land then circled Detroit airport multiple times.

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

On time departure and early arrival. Flight attendant very nice.

Wonderful! Very polite crew that was dedicated to excellent customer service

Everyone was nice but it's budget. There's nothing free and no entertainment

The flight was delayed for over an hour. No one at the gate said anything about the flight being delayed. I had to rely on my phone for updates. Absolutely no communication at the gate.

The AC broke and we were onboard for 2 hrs waiting for them to fix it. It was so hot and we could not get any water or anything to drink. They finally let us off the plane after the second attempt and we boarded a new plane. We didn't land till 12:15am!

The boarding process was simple but the seats were very uncomfortable. The staff lady was also very hard to understand when she spoke over the intercom about procedures and updates. Other staff members seemed like they were just tired and didnt want to be on the plane. Im used to happy attendants and being able to understand what is said over the speakers.

There was no flight. Call the airline and confirmed. I have no idea why you think that I flew on the days that you say I did.

They canceled my flight and never told me. There was no follow up email. I had to buy another ticket the day of.

Easy to get our TSA pre check #added. Flight crew was great and entertaining and we landed early!

Flight was delayed 6plus hours Did not take flight Customer service was terrible Will never fly again and will spread how terrible you are You stink

I didnt have a flight. Kayak must be on drugs because I confirmed with spirit that I had no booked flight.

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.