$57 Find Cheap Flights to Caribbean

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 departing on 5/27. 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.
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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cananonstop$223
Santo Domingo
Santo Domingononstop$212
Montego Bay
Montego Baynonstop$220
Nassau
Nassaunonstop$248
Kingston
Kingstonnonstop$232
Providenciales
Providencialesnonstop$328
Bridgetown
Bridgetownnonstop$327
Port of Spain
Port of Spainnonstop$273
Willemstad
Willemstad2 stops$253
St. John's
St. John's1 stop$273
Puerto Plata
Puerto Plata1 stop$290
Aguadilla
Aguadillanonstop$202
Punta Cana
Punta Cananonstop$223
Santo Domingo
Santo Domingononstop$212
Montego Bay
Montego Baynonstop$220
Nassau
Nassaunonstop$248
Kingston
Kingstonnonstop$232
Providenciales
Providencialesnonstop$328
Bridgetown
Bridgetownnonstop$327
Port of Spain
Port of Spainnonstop$273
Willemstad
Willemstad2 stops$253
St. John's
St. John's1 stop$273
Puerto Plata
Puerto Plata1 stop$290
Aguadilla
Aguadillanonstop$202

Cheap Flight Deals to Caribbean

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Caribbean 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.

Recent round-trip flight deals to Caribbean

Recommended round-trip deals departing in the coming months from the most popular airlines that fly to Caribbean.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
10:01 pm - 2:01 amEWR-SJU
4h 00mnonstop
 Logo
8:12 pm - 9:07 amSJU-EWR
12h 55m1 stop
Mon, May 26 - Thu, May 29
 Logo
10:01 pm - 2:01 amEWR-SJU
4h 00mnonstop
 Logo
8:12 pm - 9:07 amSJU-EWR
12h 55m1 stop
Sat, May 24 - Thu, May 29
Frontier Logo
10:01 pm - 2:01 amEWR-SJU
4h 00mnonstop
Frontier Logo
4:58 pm - 9:00 pmSJU-EWR
4h 02mnonstop
$163Frontier
Find Deal
Wed, May 28 - Wed, Jun 4
Frontier Logo
9:26 pm - 12:32 amMCO-SJU
3h 06mnonstop
Frontier Logo
9:30 am - 12:37 pmSJU-MCO
3h 07mnonstop
$164Frontier
Find Deal
Mon, Aug 11 - Wed, Aug 13
JetBlue Logo
3:00 pm - 6:58 pmJFK-SJU
3h 58mnonstop
JetBlue Logo
3:33 am - 7:30 amSJU-JFK
3h 57mnonstop
$201JetBlue
Find Deal
Wed, May 28 - Wed, May 28
JetBlue Logo
7:29 pm - 11:50 pmJFK-SJU
4h 21mnonstop
JetBlue Logo
3:23 am - 7:24 amSJU-JFK
4h 01mnonstop
$206JetBlue
Find Deal
Sat, Jun 14 - Mon, Jun 16
American Airlines Logo
5:25 am - 2:40 pmJFK-SJU
9h 15m1 stop
American Airlines Logo
5:30 pm - 10:09 amSJU-JFK
16h 39m1 stop
$210American Airlines
Find Deal
Sat, May 10 - Sat, May 10
Delta Logo
7:29 pm - 11:42 pmJFK-SJU
4h 13mnonstop
Delta Logo
6:10 pm - 10:29 pmSJU-JFK
4h 19mnonstop
$211Delta
Find Deal
Thu, May 15 - Wed, May 21
Delta Logo
8:05 am - 12:03 pmJFK-SJU
3h 58mnonstop
Delta Logo
5:24 pm - 9:32 pmSJU-JFK
4h 08mnonstop
$216Delta
Find Deal
Thu, Sep 25 - Sun, Sep 28
American Airlines Logo
5:25 am - 12:39 pmJFK-SJU
7h 14m1 stop
American Airlines Logo
3:50 pm - 11:00 pmSJU-JFK
7h 10m1 stop
$220American Airlines
Find Deal
Sat, May 10 - Sat, May 10
Useful Info

KAYAK's insights & trends for flights to Caribbean

Get data-powered insights and trends for flights to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Caribbean?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

The cheapest ticket to Caribbean from the United States found in the last 72 hours was to San Juan Luis Munoz Marin Intl Airport, at $93 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 $93.

What is the cheapest month to fly from the United States to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from the United States to Caribbean, 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 is September, when tickets cost $411 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $681 and $642 respectively.

How far in advance should I book a flight from the United States to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Caribbean, 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, you should book around 2 weeks 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?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Caribbean is San Juan Luis Munoz Marin Intl Airport (SJU), with an average flight price of $170.


Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$57
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from Orlando Airport to San Juan Airport

Flights to Caribbean: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Caribbean 
JoseFlew with United AirlinesIAH-SJUSep 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.
YvetteFlew with JetBlueMCO-BQNSep 2024
I liked that they changed there policy for people traveling Blue Basic they now can travel with one carryon and one backpack no extra charge
LuisFlew with SouthwestTPA-SJUJun 2024
Flight with Southwest! The crew is excellent and makes you feel secure during the flight. Only in Southwest you can flight with a carry on and two check bags without charges. Always clean airplanes and confortable.
BFlew with JetBlueBOS-AUAJun 2024
Just long enough flight you need to plan on something to occupy your time. A book, a movie etc.
Maria AlejandraFlew with FrontierJFK-SJUAug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix
BillFlew with DeltaATL-SKBMar 2024
Hope you have a newer plane where comfort plus really is comfort plus. 737-800 needs to retire.
NicoleFlew with United AirlinesEWR-POPApr 2024
Customer service accommodated my family to be seated together prior the flight! Thank God
Verified travelerFlew with United AirlinesEWR-SDQApr 2024
Early check in online, get on time for the flight
TamaraFlew with JetBlueJFK-NASMar 2024
Fly delta if you want a less rude experience.
Verified travelerFlew with Spirit AirlinesFLL-KINApr 2024
Check in very early Eat a complete meal before flying Don't be overweight
JamesFlew with FrontierSTL-PUJFeb 2024
Punta Cana airport- be ready for chaos once you get out of the airport. But it all works out well. A positive- our luggage was on the carousel as we got out of customs (so unlike STL!).
KerryFlew with United AirlinesIAH-POSDec 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 flights

  • What are the passport and visa requirements when traveling from the United States to the Bahamas?

    As a citizen of the United States, you need to have a valid passport to travel to the Bahamas and make sure that your passport remains valid during your entire length of stay in the country. It is also important to remember to keep two blank pages in your passport for entry and exit stamps from the country. If you're traveling to the Bahamas on vacation and you do not plan on staying for more than 90 days, you do not need to obtain a visa before your trip.

  • If I would like to go see the Panama Canal, what is the best way to get there from the United States?

    Most travelers want to start the journey from the United States to this world-famous landmark by flying to the Tocumen International Airport Panama (PTY). From John F. Kennedy International Airport, for example, you will find nonstop flights to this airport. Once you arrive at the airport, they are plentiful taxi options that can take you to the Panama Canal in only about 25 minutes.

  • If I would like to fly to the Caribbean and take a cruise ship back to the United States, what would be a good city to fly to?

    One of the most popular cruise ship destinations is in the eastern part of Mexico on the island of Cozumel. To travel to this area from a city in the United States like Atlanta and the Atlanta Hartsfield-Jackson International Airport (ATL), you will find nonstop flights aboard both American Airlines and United Airlines to the Cozumel Airport (CZM).

  • If I plan on traveling to Saint Lucia in July for Carnival, what are some of the best ways to get there from the United States?

    Many travelers making their way to this part of the Caribbean for this event will fly to the George F. L. Charles Airport (SLU). If you plan on making your way here from a major city like New York and John F. Kennedy International Airport, you will find one-stop flights here aboard Caribbean Airlines.

  • If I would like to travel from the United States to the Dominican Republic, what is the best airport to utilize in that country?

    One of the most popular airports in this country is the Las Américas International Airport SDQ, which has a location in the city of Santo Domingo on the southern coast of the country. When traveling from a west coast airport like Los Angeles International Airport, you will find one-stop flights aboard Spirit Airlines, American Airlines, JetBlue, and Aeromexico.

  • If I plan on traveling to Aruba, what type of travel documentation is necessary?

    Citizens of the United States need to have a valid passport that remains valid for the entire time in Aruba, and they also need to make sure they have a blank page for an entry stamp. There is no need to obtain a visa before traveling here, so long still plan on staying for more than 30 days.

  • How does KAYAK find such low prices on flights from the United States to Caribbean?

    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.

  • 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from the United States to Caribbean 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?

    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 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?

    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 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?

    Based on KAYAK data, the cheapest day to fly to Caribbean is Tuesday where round-trip tickets can be as cheap as $455. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $526 on average.

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

    The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost $351 on average. Morning departures are around 30% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean 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

  • Looking for cheap airfare to Caribbean? 25% of our users found round-trip tickets to Caribbean for the following prices or less: From Miami $359, from Chicago O'Hare Intl $650, from Newark $657
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Caribbean flight deals.
  • By far, one of the most popular destinations in the Caribbean is the city of Nassau in the Bahamas, and travelers often fly to the Lynden Pindling International Airport (NAS). From John F. Kennedy International Airport (JFK) passengers will find nonstop flights to this airport or JetBlue and Delta Airlines.
  • One destination that is quite often overlooked in the Caribbean that is a beautiful place for a vacation is Bermuda. One of the best features of this island nation is that the L.F. Wade International Airport (BDA) has one-stop flights available from airports in the United States, such as Philadelphia International Airport (PHL) and Washington Dulles International Airport (IAD).
  • A popular destination in the Caribbean for travelers from the United States is Luis Munoz Marin International Airport (SJU) because Puerto Rico is a territory of the United States, making it quite easy to travel here without any immigration and customs hassles.
  • Maybe one of the best-known tropical destinations in the Caribbean is Montego Bay, and when traveling from large airports like John F. Kennedy International Airport (JFK), passengers will find nonstop flights aboard both JetBlue and Caribbean airlines to Sangster International Airport (MBJ) in Montego Bay.
  • A unique destination in the Caribbean is Turks and Caicos and when passengers want to travel here from the central portion of the United States and airports like Chicago O' Hare International Airport (ORD), they can find very convenient one-stop flights aboard American Airlines.
  • A popular destination for the spring break crowd heading away from college in the United States is to travel to Cancun on the eastern coast of the Yucatán peninsula. Travelers on the west coast of the United States leaving from airports like Los Angeles International Airport (LAX) will find one-stop flights aboard American Airlines to Cancun International Airport (CUN).
  • Parents that will be traveling with children to the Dominican Republic who plan on renting a car should know that children up to the age of six need to travel in a forward-facing car seat, and then up to the age of 12 need to travel in a booster seat. All children 12 years of age and younger need to travel in the rear seat.

Top 5 airlines flying to Caribbean

Need help choosing which airline to fly with from the United States to Caribbean? 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.
8.0
DeltaOverall score based on 7936 reviews
7.9Comfort
7.3Food
8.2Boarding
7.9Entertainment
8.5Crew
Airline reviews

Our bag was lost so that made unnecessary chaos On our trip

6.0 GoodBarbara, Apr 2025JFK - FCO
Read more Delta reviews

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

Everything is good except the dinner and breakfast. The sandwich is very delicious. Toilet is clean, I only use one of them. Flight attendants are very nice. 👍👍

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Multiple delays and not straight answer from the United team

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

I didn’t get on plane. Passport being processed by consulate with visa application. Tried to cancel through underpricer after purchasing cacelling for any reason. No dice, they are thieves.

Electric plugs didn't work. Entertainment system wasn't working

Excellent from start to finish. All staff members were amazing!

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Everything you need to know for your flight to Caribbean

Cabin class types available on flights to Caribbean

Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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