$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
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 Cananonstop$236
Santo Domingo
Santo Domingononstop$244
Montego Bay
Montego Bay1 stop$250
Nassau
Nassaunonstop$264
Kingston
Kingstonnonstop$355
Providenciales
Providenciales1 stop$347
Port of Spain
Port of Spainnonstop$282
Bridgetown
Bridgetown1 stop$304
Willemstad
Willemstad2 stops$271
Aguadilla
Aguadillanonstop$169
Puerto Plata
Puerto Plata1 stop$312
St. John's
St. John'snonstop$413
Punta Cana
Punta Cananonstop$236
Santo Domingo
Santo Domingononstop$244
Montego Bay
Montego Bay1 stop$250
Nassau
Nassaunonstop$264
Kingston
Kingstonnonstop$355
Providenciales
Providenciales1 stop$347
Port of Spain
Port of Spainnonstop$282
Bridgetown
Bridgetown1 stop$304
Willemstad
Willemstad2 stops$271
Aguadilla
Aguadillanonstop$169
Puerto Plata
Puerto Plata1 stop$312
St. John's
St. John'snonstop$413

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

Thu, May 7 - Sun, May 10
Frontier Logo
6:15 am - 12:21 am
MCO
-
SJU
18h 06m
1 stop
Frontier Logo
6:09 pm - 9:30 pm
SJU
-
MCO
3h 21mnonstop
$166Frontier
Fri, May 8 - Thu, May 14
Frontier Logo
6:15 am - 12:21 am
MCO
-
SJU
18h 06m
1 stop
Frontier Logo
3:03 am - 6:10 am
SJU
-
MCO
3h 07mnonstop
$167Frontier
Fri, May 8 - Fri, May 15
Frontier Logo
6:15 am - 12:21 am
MCO
-
SJU
18h 06m
1 stop
Frontier Logo
7:20 am - 9:53 pm
SJU
-
MCO
14h 33m
1 stop
$168Frontier
Tue, Jun 2 - Tue, Jun 16
JetBlue Logo
9:30 pm - 1:38 am
JFK
-
SJU
4h 08mnonstop
JetBlue Logo
1:12 pm - 5:20 pm
SJU
-
JFK
4h 08mnonstop
$244JetBlue
Tue, Jun 23 - Tue, Jun 30
JetBlue Logo
6:15 pm - 10:31 pm
JFK
-
SJU
4h 16mnonstop
JetBlue Logo
7:25 am - 11:28 am
SJU
-
JFK
4h 03mnonstop
$252JetBlue
Tue, Jun 23 - Tue, Jun 30
Delta Logo
7:25 pm - 11:43 pm
JFK
-
SJU
4h 18mnonstop
Delta Logo
5:45 pm - 10:01 pm
SJU
-
JFK
4h 16mnonstop
$257Delta
Tue, Aug 11 - Wed, Aug 12
American Airlines Logo
8:30 pm - 9:43 am
JFK
-
SJU
13h 13m
1 stop
American Airlines Logo
1:38 pm - 9:30 pm
SJU
-
JFK
7h 52m
1 stop
$261American Airlines
Tue, May 12 - Wed, May 13
American Airlines Logo
2:30 pm - 8:51 pm
JFK
-
SJU
6h 21m
1 stop
American Airlines Logo
7:25 am - 10:16 pm
SJU
-
JFK
14h 51m
1 stop
$265American Airlines
Tue, May 5 - Wed, May 13
Delta Logo
8:30 am - 12:40 pm
JFK
-
PUJ
4h 10mnonstop
Delta Logo
1:48 pm - 6:00 pm
PUJ
-
JFK
4h 12mnonstop
$353Delta
Sun, May 3 - Wed, May 6
United Airlines Logo
11:21 am - 3:12 pm
EWR
-
STI
3h 51mnonstop
United Airlines Logo
6:00 am - 10:00 am
STI
-
EWR
4h 00mnonstop
$422United Airlines
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 Boston (BOS) 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 $476 on average, and Boston to Oranjestad, which costs $526 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 $443 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$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 $428. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $477 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 $310, from Chicago O'Hare Intl $510, from Newark $523
  • 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 8438 reviews
8.5Crew
7.9Comfort
7.8Entertainment
7.2Food
8.1Boarding
Airline reviews

Everything was great. The only issue is unfixable. Seats are too small. 😁🤪

10.0 ExcellentAnonymous, Apr 2026
ATL - AMS
Read more Delta reviews

Everything was great. The only issue is unfixable. Seats are too small. 😁🤪

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

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.

They told us yesterday APR21st that they were cleaning the plane and we got delayed. After that they said they didn't had any crew for the flight so they cancelled the flight till next day.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Flight itself excellent, but delayed so missed connection & got to destination 2 hrs later

The flight crew on this leg of my trip was very friendly and pleasant. Every one of them was humorous, as well as helpful and accommodating. This group was BY FAR the best crew I’ve flown with. They deserve kudos.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was delayed from take off because only one runway was operational in San Francisco.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Really hard landing... as in slammed into the runway then hit the brakes really hard ...

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

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.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

Entertainment and wifi were very sub-par - audio issues and no wifi

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

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

As we approached Denver, we encountered quite a bit of turbulence. I know this can sometimes be the case as I frequently fly this route but not on American. My gripe: Usually a pilot or co-pilot alerts passengers to the possibility of turbulance ahead of time. This did not occur nor did he communiucate during what was a pretty rough ride.

The staff was nice. I appreciated that I was able to take an earlier flight, even though it was last minute. The boarding process felt rather chaotic.

Overall a good experience, however Wifi was not working on the flight.

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

Airlines should be prohibited from using the seats they get away with.

My flight got delayed a total of five times. And the boarding gate changed four times. most of the time the platform was not up-to-date with the changes taking place. The most discouraging part of the entire trip by far.

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

American delayed the flight for a crew rest period. The delay occurred late in the evening - the earliest i can find is 10:20 pm. With a 6 am flight anyone on the flight would have already have been asleep (unless you are insane, a vampire or on drugs) and at least for me i was already on the way to the airport at 445 am the next morning when i discovered they delayed the flight until 9 am. Given the incoming flight was in the air at 6 pm the evening before this should have been figured out a lot more timely that was there only crew to use. Just frustrating given there is no consideration for customer experience anymore in flying.

Returned home with a blood clot from flight homes and the uncomfortable aircraft I was on.

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.

We were surprised to be charged $99 for a personal item. And of course everything offered on the flight was an additional charge. Other than that the pilot flew and landed the plane well and the attendants and fellow passengers were nice enough.

baggage drop off was a bit much. I felt like I worked for spirit airlines since I did all the work.

Gate changed multiple times. The staff seemed annoyed that we asked for water. We had to pay for the water as well.

It was a full Spirit experience. Got to witness police officers having to deboard a passenger and cost us about an hour of delay. Front seat was spacious and better than expected.

Broke my bag and offered no support or solution afterwards

We didn't get on the flight, they canceled our flight and said there was no flights leaving this weekend and sent me our money back.

Horrible company: canceled flights and delayed flights. Spirit canceled my flight from Miami to Philadelphia the day before we were supposed to leave from Philadelphia to Miami, with no explanation. I had to rebook another flight, spending more money and instead of flying from Miami, I had to choose a flight from Fort Lauderdale because there were no direct flights available from Miami. That created additional cost. The flight with Spirit from Fort Lauderdale was scheduled to depart at 6am, so I had to wake up my 3 and 6 years old at 3am to get to the airport in time and then, at 5am while we were at the gate the delayed the flight until 7:45am with again no explanation.

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.