$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 1/17. 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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Cheap Flights to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$205
Santo Domingo
Santo Domingononstop$221
Montego Bay
Montego Baynonstop$221
Nassau
Nassaunonstop$249
Kingston
Kingstonnonstop$252
Providenciales
Providenciales1 stop$245
Port of Spain
Port of Spain1 stop$235
Bridgetown
Bridgetownnonstop$327
Willemstad
Willemstad2 stops$221
St. John's
St. John'snonstop$305
Puerto Plata
Puerto Plata1 stop$324
Aguadilla
Aguadillanonstop$136
Punta Cana
Punta Cananonstop$205
Santo Domingo
Santo Domingononstop$221
Montego Bay
Montego Baynonstop$221
Nassau
Nassaunonstop$249
Kingston
Kingstonnonstop$252
Providenciales
Providenciales1 stop$245
Port of Spain
Port of Spain1 stop$235
Bridgetown
Bridgetownnonstop$327
Willemstad
Willemstad2 stops$221
St. John's
St. John'snonstop$305
Puerto Plata
Puerto Plata1 stop$324
Aguadilla
Aguadillanonstop$136

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, Jan 24 - Mon, Jan 26
Frontier Logo
1:00 pm - 5:58 pm
JFK
-
SJU
3h 58mnonstop
Frontier Logo
4:36 pm - 3:27 pm
SJU
-
JFK
23h 51m1 stop
$148Frontier
Tue, Jan 20 - Thu, Feb 5
Spirit Airlines Logo
7:30 am - 6:49 pm
LGA
-
SJU
10h 19m1 stop
Spirit Airlines Logo
11:52 am - 7:00 pm
SJU
-
LGA
8h 08m1 stop
$148Spirit Airlines
Tue, Jan 20 - Thu, Jan 22
JetBlue Logo
7:45 am - 6:07 pm
ORD
-
SJU
8h 22m1 stop
JetBlue Logo
11:06 am - 7:36 pm
SJU
-
ORD
10h 30m1 stop
$196JetBlue
Fri, Feb 27 - Fri, Mar 6
JetBlue Logo
12:41 pm - 12:29 am
ORD
-
SJU
9h 48m1 stop
JetBlue Logo
3:05 pm - 10:56 pm
SJU
-
ORD
9h 51m1 stop
$202JetBlue
Fri, Jan 9 - Wed, Jan 14
Delta Logo
11:25 am - 4:21 pm
JFK
-
PUJ
3h 56mnonstop
Delta Logo
2:55 pm - 6:15 pm
PUJ
-
JFK
4h 20mnonstop
$283Delta
Thu, Jan 22 - Thu, Jan 29
American Airlines Logo
3:44 pm - 4:26 pm
JFK
-
PUJ
23h 42m1 stop
American Airlines Logo
6:02 pm - 10:04 am
PUJ
-
JFK
17h 02m1 stop
$284American Airlines
Sat, Feb 28 - Wed, Mar 4
American Airlines Logo
7:00 pm - 2:58 pm
JFK
-
PUJ
18h 58m1 stop
American Airlines Logo
5:57 pm - 9:57 am
PUJ
-
JFK
17h 00m1 stop
$285American Airlines
Thu, Jan 29 - Sun, Feb 1
Arajet Logo
11:59 pm - 11:05 am
EWR
-
PUJ
10h 06m1 stop
Arajet Logo
7:10 pm - 10:30 pm
PUJ
-
EWR
4h 20mnonstop
$286Arajet
Tue, Mar 3 - Sat, Mar 7
Delta Logo
11:25 am - 4:21 pm
JFK
-
PUJ
3h 56mnonstop
Delta Logo
3:05 pm - 6:25 pm
PUJ
-
JFK
4h 20mnonstop
$288Delta
Sun, Mar 22 - Sat, Mar 28
Arajet Logo
12:00 pm - 4:26 pm
EWR
-
PUJ
4h 26mnonstop
Arajet Logo
7:15 pm - 11:35 pm
PUJ
-
EWR
4h 20mnonstop
$293Arajet
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 $103 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 $110.

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 $372 on average. The cheapest price found on KAYAK in the last 2 weeks was $49 for the route New York LaGuardia Airport (LGA) to Oranjestad (AUA). The most popular routes on KAYAK are Hartford to Montego Bay which costs $370 on average, and Orlando to Oranjestad, which costs $431 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 March, when the average cost of round-trip tickets is $452 and $363 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 2 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 $164.

Good to know

Low seasonSeptember
Cheapest flight$78
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 19% 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 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 $471. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $530 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 $261, from Chicago O'Hare Intl $480, from Newark $483
  • 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 8018 reviews
8.1Boarding
7.9Comfort
7.9Entertainment
8.5Crew
7.3Food
Airline reviews

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

10.0 ExcellentNguyen, Dec 2025
DCA - SEA
Read more Delta reviews

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

Sat next to a one year old. She crawled all over the place and made me laugh.

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

They did the one thing that really matters - got to Chicago early.

I liked the snacks and the flight attendants were friendly.

Gate agent at Frankfurt was terrible. She denied PRE boarding even as it was printed on the boarding pass. Refused to look at the boarding pass and literally shouting for no reason. Frankfurt airport has horrible and rude staff who avoids trying to answer any question at all. Overall, horrible experience.

The Crew and the food was the worst I ever had in Business Class. First they told us there were no space for carry on. It was plenty of space over our 2 row seats, we had to ask to let us travel with it which was accepted. They were aware that we had to run for the connection due to the previous flight delay. Have us one hour waiting for more customers and not even offer a glass of water. Then started the service and they started to serve other passengers drinks in business and did not offer any drinks until they serve our pre ordered meal and I ask for something to drink. I had to wait until they finished to serve all passengers until Inget something. The crew was the worts I ever had for Business Class in my life.

Very turbulent trip made it pretty bearable, plus the lack of refreshments served and the lack of any air conditioning before takeoff which took an hour or more.

Flight was late - I was downgraded from first class to coach

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Not a pleasant experience, service was poor. Didn't like it

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

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

A flight attendant was extremely friendly and offered to move me to a row that was less crowded

Awful!!! Spirit cancelled my flight just 4 hours before departure- with no alternative flights available. I ended up missing a huge family gathering because I wasn’t able to get out. Such An awful experience. And on top of that, all the buckle and dime-ing for bags. I will never book with Spirit EVER

Spirit has improved a lot since I flew with it in 2011. I give the airline a huge thumbs up!!

My flight was cancelled for “weather”. There was absolutely no bad weather along the course of my flight track. I missed my entire vacation with my family. I will never book a flight with spirit again

Flight was cancelled 2.5 before departure without warning. Staff was rude and lied to us pre-security.

I'd have like to check my bag and not toss my hair products.sears are very uncomfortable. And that even water isn't free really sucks. The ticket was almost $400

Terrible. They cancelled the flight at the last minute after I had checked in at the airport and then told me they could only put me on a flight after 7 days. Pathetic.

Terrible they canceled the flight very sheepishly and ended up costing me 1200 dollars and kayak and xcover are doing nothing

It’s Spirit need I say more? Thank this little airline because without it the other airlines would raise their prices so much I wouldn’t be able to fly anywhere. It’s affordable and gets you where you need to go! I’m not flying to get a free bag of chips, y’know?

Spirit cancelled the flight very late last night, I was on the way to the airport when I found out

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.