$85 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 3/23. 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 23% 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 Cana2 stops$273
Santo Domingo
Santo Domingononstop$211
Montego Bay
Montego Bay1 stop$244
Nassau
Nassaunonstop$267
Kingston
Kingstonnonstop$302
Providenciales
Providenciales1 stop$337
Port of Spain
Port of Spainnonstop$284
Bridgetown
Bridgetown1 stop$314
Willemstad
Willemstad2 stops$213
Puerto Plata
Puerto Plata2 stops$325
St. John's
St. John'snonstop$369
Aguadilla
Aguadillanonstop$163
Punta Cana
Punta Cana2 stops$273
Santo Domingo
Santo Domingononstop$211
Montego Bay
Montego Bay1 stop$244
Nassau
Nassaunonstop$267
Kingston
Kingstonnonstop$302
Providenciales
Providenciales1 stop$337
Port of Spain
Port of Spainnonstop$284
Bridgetown
Bridgetown1 stop$314
Willemstad
Willemstad2 stops$213
Puerto Plata
Puerto Plata2 stops$325
St. John's
St. John'snonstop$369
Aguadilla
Aguadillanonstop$163

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

Sun, May 3 - Sun, May 10
Frontier Logo
8:39 pm - 12:29 am
PHL
-
SJU
3h 50mnonstop
Frontier Logo
6:30 am - 10:41 am
SJU
-
PHL
4h 11mnonstop
$168Frontier
Tue, Apr 14 - Sat, Apr 18
Spirit Airlines Logo
6:48 am - 6:55 pm
PHL
-
SJU
12h 07m
1 stop
Spirit Airlines Logo
2:09 am - 6:12 am
SJU
-
PHL
4h 03mnonstop
$169Spirit Airlines
Fri, Apr 10 - Thu, Apr 16
Frontier Logo
7:00 pm - 2:01 am
PHL
-
SJU
7h 01m
1 stop
Frontier Logo
6:00 am - 1:59 pm
SJU
-
PHL
7h 59m
1 stop
$176Frontier
Tue, Apr 21 - Tue, Apr 21
Frontier Logo
6:50 am - 5:59 pm
PHL
-
SJU
11h 09m
1 stop
Frontier Logo
3:08 am - 10:38 am
SJU
-
PHL
7h 30m
1 stop
$181Frontier
Fri, Apr 17 - Thu, Apr 23
Multiple Airlines Logo
9:02 pm - 12:54 am
PHL
-
SJU
3h 52mnonstop
Multiple Airlines Logo
1:59 am - 6:08 am
SJU
-
PHL
4h 09mnonstop
$182Multiple Airlines
Sun, Apr 26 - Wed, Apr 29
Frontier Logo
2:17 pm - 6:07 pm
PHL
-
SJU
3h 50mnonstop
Frontier Logo
4:35 pm - 8:44 pm
SJU
-
PHL
4h 09mnonstop
$183Frontier
Sat, May 2 - Sat, May 9
Multiple Airlines Logo
8:39 pm - 12:29 am
PHL
-
SJU
3h 50mnonstop
Multiple Airlines Logo
2:09 am - 6:12 am
SJU
-
PHL
4h 03mnonstop
$184Multiple Airlines
Thu, Apr 16 - Mon, Apr 20
Spirit Airlines Logo
9:02 pm - 12:54 am
PHL
-
SJU
3h 52mnonstop
Spirit Airlines Logo
2:09 am - 6:12 am
SJU
-
PHL
4h 03mnonstop
$186Spirit Airlines
Mon, Apr 20 - Tue, Apr 21
JetBlue Logo
9:59 pm - 9:58 am
JFK
-
PUJ
11h 59m
1 stop
JetBlue Logo
7:20 pm - 11:22 pm
PUJ
-
JFK
4h 02mnonstop
$319JetBlue
Tue, May 19 - Tue, May 19
JetBlue Logo
10:55 am - 2:49 pm
JFK
-
PUJ
3h 54mnonstop
JetBlue Logo
5:13 pm - 1:56 am
PUJ
-
JFK
8h 43m
1 stop
$321JetBlue
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 $131 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 $131.

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 $382 on average. The cheapest price found on KAYAK in the last 2 weeks was $54 for the route Atlanta (ATL) to Oranjestad (AUA). The most popular routes on KAYAK are Boston to Oranjestad which costs $516 on average, and Hartford to Punta Cana, which costs $401 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 $337 respectively.

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

The average price for all round-trip flights from the United States to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $934 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $934.

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 $146.

Good to know

Low seasonSeptember
Cheapest flight$82
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Baltimore to San Juan

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 $421. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $471 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 Washington, D.C. Reagan-National $454, from Newark $472, from Chicago O'Hare Intl $494
  • 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 8303 reviews
7.2Food
8.1Boarding
7.8Entertainment
7.9Comfort
8.5Crew
Airline reviews

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

2.0 MediocreJaka, Mar 2026
MSP - SEA
Read more Delta reviews

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Business class seats felt very cramped compared to other airlines.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Both flights were significantly delayed. The flight experience itself was great.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

Perhaps this is an airport issue, but being in a takeoff queue for over an hour in the taxiing lane is unacceptable. We will definitely be seeking alternative avenues for air travel in the future.

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

Mostly good. The WiFi wasn’t working so that was not great.

I rated the experience "mediocre" because of the 2 hour delay in take off. This is the 4th flight from DFW on AA where there was a delay and in one of the instances (after 13 delays), the flight was cancelled. I understand weather but for the March 18th flight, there was no weather issue in Dallas or Detroit. I called Concierge Key and they were wonderful, booking me on a later flight in case my flight was cancelled. I have flown with American for many years and never has there been this consistent pattern of delays. Very disappointing.

They put me on an earlier and I got home sooner

Not good. One of my luggage is missing. And until now they can’t find it

Horrible experience upon landing. Probably more due to DCA utter incompetence than AA.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

My 9:50AM flight was delayed to 3:40PM "due to incoming aircraft delay". No aircraft is "delayed" that long. Found out once we did board (after several changes in times) that the aircraft had a maintenance issue and we had to wait for another aircraft. Just tell us that. The aircraft we did get was old and the seats need to be updated. I have been traveling for several weeks with AA and you should refresh your entertainment content as frequent flyers have gone through most of your new content. I have Celiac and a shellfish allergy and continue to have struggles with meals on business and first class flights. Please keep this in mind. Sorry - was a long travel day yesterday and a bit cranky this morning with my experience comments. Still an AA fan.

I was in the airport when I'll check the status of my flight and it was canceled and without any reason. The worst of the worst ...

I never had an opportunity to experience them! They cancelled my flight TWICE!!!

Return flight was canceled. Needed to reschedule with another airline the next day. Cost an an additional $84. At another airport 45 miles further away

Spent seven hours in the airport with spirit pushing he flight time back two hours every two hours only to then have it canceled without explanation. The employees said, “They’ve been doing this for the last five days.” Would have been great if they told us to expect that when we arrived.

Seat do not reclined and tight space. Flight changed so many times hard to keep up.

Bad airline to travel with my flight was delayed for more than 3 hours they act like it’s normal

No WiFi, no outlets to charge phones, no complimentary beverages on a 6 hour flight

Length of flight was fine Delay of over 3 hours was very bad!! Flight down was delayed 1.5 hours

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Absolutely terrible, flight was cancelled and we missed our cruise. Will never fly Spirit again.

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.