$78 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 5/11. 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
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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 Cana1 stop$260
Santo Domingo
Santo Domingononstop$244
Montego Bay
Montego Baynonstop$272
Nassau
Nassaunonstop$258
Kingston
Kingstonnonstop$325
Providenciales
Providenciales1 stop$346
Port of Spain
Port of Spain1 stop$308
Bridgetown
Bridgetown1 stop$304
Willemstad
Willemstad2 stops$262
Aguadilla
Aguadillanonstop$202
Puerto Plata
Puerto Plata1 stop$322
St. John's
St. John's1 stop$430
Punta Cana
Punta Cana1 stop$260
Santo Domingo
Santo Domingononstop$244
Montego Bay
Montego Baynonstop$272
Nassau
Nassaunonstop$258
Kingston
Kingstonnonstop$325
Providenciales
Providenciales1 stop$346
Port of Spain
Port of Spain1 stop$308
Bridgetown
Bridgetown1 stop$304
Willemstad
Willemstad2 stops$262
Aguadilla
Aguadillanonstop$202
Puerto Plata
Puerto Plata1 stop$322
St. John's
St. John's1 stop$430

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

Sat, May 16 - Wed, May 20
Frontier Logo
11:20 pm - 2:08 am
MCO
-
SJU
2h 48mnonstop
Frontier Logo
7:30 am - 9:53 pm
SJU
-
MCO
14h 23m
1 stop
$166Frontier
Tue, Jun 2 - Sat, Jun 6
Frontier Logo
6:15 am - 3:50 pm
MCO
-
SJU
9h 35m
1 stop
Frontier Logo
8:13 pm - 11:29 pm
SJU
-
MCO
3h 16mnonstop
$169Frontier
Tue, Jun 2 - Wed, Jun 10
Frontier Logo
6:15 am - 3:50 pm
MCO
-
SJU
9h 35m
1 stop
Frontier Logo
6:05 pm - 9:19 pm
SJU
-
MCO
3h 14mnonstop
$170Frontier
Sun, May 17 - Sat, May 23
Spirit Airlines Logo
7:00 am - 10:44 am
PHL
-
SJU
3h 44mnonstop
Spirit Airlines Logo
1:30 am - 5:35 am
SJU
-
PHL
4h 05mnonstop
$180Spirit Airlines
Tue, May 26 - Fri, May 29
Spirit Airlines Logo
6:42 pm - 10:42 pm
EWR
-
SJU
4h 00mnonstop
Spirit Airlines Logo
12:59 am - 5:06 am
SJU
-
EWR
4h 07mnonstop
$218Spirit Airlines
Sun, Aug 23 - Wed, Aug 26
American Airlines Logo
5:14 pm - 11:07 pm
ORD
-
SJU
4h 53mnonstop
American Airlines Logo
7:14 pm - 7:34 am
SJU
-
ORD
13h 20m
1 stop
$222American Airlines
Wed, Aug 19 - Wed, Sep 2
Delta Logo
11:10 am - 10:23 pm
ORD
-
SJU
10h 13m
1 stop
Delta Logo
5:45 pm - 11:57 pm
SJU
-
ORD
7h 12m
1 stop
$226Delta
Wed, Aug 19 - Wed, Sep 2
American Airlines Logo
5:14 pm - 11:07 pm
ORD
-
SJU
4h 53mnonstop
American Airlines Logo
6:51 am - 2:15 pm
SJU
-
ORD
8h 24m
1 stop
$227American Airlines
Mon, Jun 8 - Wed, Jun 17
JetBlue Logo
6:40 pm - 10:53 pm
JFK
-
SJU
4h 13mnonstop
JetBlue Logo
7:25 am - 11:28 am
SJU
-
JFK
4h 03mnonstop
$264JetBlue
Tue, Jun 9 - Tue, Jun 23
JetBlue Logo
9:30 pm - 1:38 am
JFK
-
SJU
4h 08mnonstop
JetBlue Logo
5:01 am - 8:54 am
SJU
-
JFK
3h 53mnonstop
$265JetBlue
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 $125 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 $125.

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 $396 on average. The cheapest price found on KAYAK in the last 2 weeks was $55 for the route Jacksonville (JAX) to San Juan Luis Munoz Marin Intl Airport (SJU). The most popular routes on KAYAK are Hartford to Punta Cana which costs $387 on average, and New York to Oranjestad, which costs $540 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 $342 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 Georgetown Exuma Intl Airport (GGT), with an average flight price of $142.

Good to know

Low seasonSeptember
Cheapest flight$78
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 $432. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $481 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 $347, from Newark $473, from Chicago O'Hare Intl $590
  • 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 8458 reviews
8.5Crew
8.1Boarding
7.2Food
7.9Comfort
7.8Entertainment
Airline reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

8.0 ExcellentMatthew, May 2026
OKC - ATL
Read more Delta reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

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.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Cree was organized and pleasant. Plane had good seating but as it’s a shuttle toilets hadn’t been thoroughly cleaned (eg. bins too full)

I liked that my son and I were reseated next to each other (we had different bookings). I liked that it was a directg flight and mostly on time. I liked that you provided pillows and blankets. Flight attendants were generally courteous. The messaging through wifi did not work well. The food was not good. Seats are very narrow and I felt slightly claustraphobic in the window seat.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

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.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

The crew was very attentive through out the flight. Seats were comfortable, nice flight bag with pillow and blanket. Food was okay, since it was a overnight flight seemed to go by fast.

The flight attendant on my side of business class seemed like a novice and did not provide good service. Otherwise the flight was good and the entertainment system was very good. No free WiFi.

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

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

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

There was a screen but no earphones that could use the older input so I could listen to anything.

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

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.

Had a flight change had to get a credit.will I get my money back.

Shut down without prior notice End up with spending lots of extra $$$

There was a crack in my window seal. And Spirit is now closed forever.

The company went out of business and now I'm stuck in Ft. Lauderdale. Would not recommend.

Spirit changed flight times by 12 hours with coming and going so I refunded tickets and drove

The airline cancel mi flight, lost a lot of money!!!

They closed the doors earlier than posted. I missed my flight with a slim 5 minutes bc they closed the doors earlier than earlier. My luggage never made it onto the flight and I had to find a new flight to Dallas bc the only option they could rebook me on was for leaving miami.

The agent cancel my flight without my consent. So the situation generate me a lot of troubles, specially because we were traveling with a baby

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

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.