$104 Find Cheap Flights to Caribbean - Compare and Save

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Cheap Flights to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$329
Santo Domingo
Santo Domingononstop$279
Montego Bay
Montego Baynonstop$351
Nassau
Nassaunonstop$287
Kingston
Kingston1 stop$386
Providenciales
Providenciales1 stop$312
Port of Spain
Port of Spain1 stop$252
Bridgetown
Bridgetown1 stop$370
Willemstad
Willemstad2 stops$266
Aguadilla
Aguadillanonstop$185
St. John's
St. John's1 stop$430
Puerto Plata
Puerto Plata1 stop$399
Punta Cana
Punta Cana1 stop$329
Santo Domingo
Santo Domingononstop$279
Montego Bay
Montego Baynonstop$351
Nassau
Nassaunonstop$287
Kingston
Kingston1 stop$386
Providenciales
Providenciales1 stop$312
Port of Spain
Port of Spain1 stop$252
Bridgetown
Bridgetown1 stop$370
Willemstad
Willemstad2 stops$266
Aguadilla
Aguadillanonstop$185
St. John's
St. John's1 stop$430
Puerto Plata
Puerto Plata1 stop$399
Booking Insights

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?

The cheapest ticket to Caribbean from the United States found in the last 5 days was to San Juan Luis Munoz Marin Intl Airport, at $105 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 5 days was $105.

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

The cheapest month for flights from the United States to Caribbean is January, when tickets cost $187 (return) on average. On the other hand, the most expensive months are July and December, when the average cost of round-trip tickets is $285 and $259 respectively.

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

To get a below average price on the flight from the United States to Caribbean, you should book around 4 weeks before departure, which saves you about 17% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 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 Freeport Grand Bahama Intl Airport (FPO), with an average flight price of $152.

Good to know

Low season

September

Cheapest flight

$104
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Chicago O'Hare Airport to San Juan

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

Insights shared by verified travelers who flew to Caribbean 
SteveFlew with Spirit Airlines-Apr 2026
Earlier is better for accuracy. Later is better to avoid crowds
SephanyahFlew with Caribbean Airlines-Nov 2025
Reach on time for you check-in or use web check-in.
Verified travelerFlew with Frontier-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-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-Aug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix
Verified travelerFlew with Spirit Airlines-Apr 2024
Check in very early Eat a complete meal before flying Don't be overweight
Verified travelerFlew with United Airlines-Apr 2024
Early check in online, get on time for the flight
NicoleFlew with Spirit Airlines-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-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 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 $473. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $515 on average.

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 $389, from Newark $594, from Chicago O'Hare Intl $628
  • 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.

Reviews of the 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.
7.8
DeltaOverall score based on 8500 reviews
7.8Comfort
8.1Boarding
8.5Crew
7.2Food
7.8Entertainment
Airline reviews

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

4.0 OkayJeff, Aug 2026
Read more Delta reviews

The plane was a rather tired 737-800, with old style small luggage bins. Poor air flow. USB charger in the infotainment system was not functioning. The flight was 2 hours late due to crew rest requirements (not their fault). On arrival in Seattle, waited on the tarmac for 30 minutes with very few updates from the crew.

Flight was delayed and we were on the runway after landing for 30 mins

The plane is old. There was water dripping fown from the air cooling system. The toilets were mot that clean

We were delayed so pilots can rest and had no WiFi the whole trip. First class seats are small compared to other planes

The experience was bad. Flight was delayed to handle maintenance (understandable) but still there was some dew forming and dropping as droplets on few seats. Internet at best was allowing some browsing but at a snail pace.

We were delayed 2 hours because of a broken seat. Other than that it was a very nice flight.

There needs to be better accommodations for waiting passengers. A a designated standing space that is separated and away from concourse traffic.

My seats are comfortable because I choose to fly in the exit rows and this time upgraded to first class with minimum sky miles. Otherwise, I would not be happy in regular seats or even middle comfort seats. Onboarding on the return flight from Nashville to Atlanta was hot and very uncomfortable for over 30 minutes due to extreme hot weather. However, Delta should provide some other air flow option as it was almost unbearable until 10 minutes after take-off. First class seats should be equipped with cup holders. Currently, the middle console is used and is flat and prone to spilling drinks.

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

wifi too slow or would not connect and entertainment kept on freezing

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Very Poor. Significant delays getting to Chicago and then very poor communication on delays in Chicago to Cleveland. We could have rented a car and driven there faster than the delays ended up being.

A little more friendliness from that crew of the day.

The app logs you out right when you are boarding requiring all passwords and reservation number for the flight. Super annoying

The pre-order only approach for fresh food is really challenging

This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.

Staff didn't seem confident about the ingredients in my lactose intolerance meal

the seat has a problem. the back had a hole.

The back to back mechanical delays from Denver to San Diego and then on my return flight from Denver to Great Falls it added extra time both ways

Really old place. Not as clean as it should be, tray tables needed better cleaning. The items, trays and some other items need to b6 engineered. Anything task you or crew may do is incredibly load, seriously engineer for quiet smooth, easy. Just opening and closing the tray table is actually dangerous and can easily injure a finger. I'm sure it happens as it happened to me! First time I used United and likely will be the last!

Luggage handling and communication is extremely poor. I landed in india 15th and recived luggage today. Based on my itag the luggage was in Germany. They kept me in dark. Etihad num er in india was non operatuonal. Had to call USA etihad. It should not be so difficullt. I came for 1 week business trip everything was screwed . This is the first and also will be last for me

There was no service on the flight even though there was no turbulence or any other issues on the flight. Nobody greeted at the entry or leaving the airplane, staff crew looked annoyed and not helpful at all.

mechanical problem delayed more than 2 hours on the run way.

I paid extra for a seat up front and at last minute was moved to the 2nd to last row - which I could have had for free. No reason and no refund. Really great customer service American

You guys broke my bag so not good, and that was the cherry on top after a 4 hour delay, change of gates, etc.

I have to sit in the middle for more than five hours because the first flight was delayed. Terrible experience. No more American Airlines.

The first flight was delayed by an hour and a half, so we missed the second flight. They rebooked us on the later flight and I have to sit in the middle for more than 5 hours. Terrible experience. No more American Airlines.

I paid extra for what I thought was leg room and it certainly was not. I had a very cramped experience on my flight from Dallas to Detroit and it was the section right behind first class section. I did however have an amazing flight from Atlanta to Dallas on the initial outbound flight.

The boarding process was slow and we had a delay on the tarmac, not the fault of the airline. They had ZERO food options available for purchase which shouldn't happen.

Once again the staff of American Airlines is kind, helpful, efficient, and professional.

My screen didn’t work, my seat didn’t recline, the flight attendant was rude and completely dismissive, the airplane was freezing, the seats are way old, slanted and uncomfortable. I payed for a full ticket and got a horrific experience, with a flight attendant who dismissed me even though I was calm respectful and polite.

Very poor help no one answering a question regarding seating. Very rude staff. They don’t care, as if it’s not part of their job. Flight was delayed for no good reason and no apologies given.

It was my worse flying experience. It was my first time and last time flying with Jet Blue.

The wifi didn't work and I needed to do some work. This was a business trip.

It was my first time in Jetblue flight in 10+ years(?) and the experience was horrible. You were better before. There were ATC delays sitting/waiting in the tarmac for 2 hours, I understand that this isn't Jetblue's problem but how the matter was handled poorly is. Cabin was so warm and hot couldn't get it to cool down for the entire waiting period worse, even during cruise flight. Start, the passengers were spoken to and treated like a little children with no respect. Constant/multiple annoying tone/voice PA announcements of mentioning "... only big/large suitcases are for the bin and small ones need to be placed under the seat, etc,..." I see that flight was delayed and crew were trying to get the plane ready to board as soon as they can but the way they presented was lack of better word, condesending and scolding tone to cattle. It was definite unpleasant, unwelcoming flight experience I have ever had with Jetblue. Whatever happen to smiles and fun employees , pleasant/helpful gate agents, flight attendants, crews, where have they gone? It was dissapointing flight experience overall from everyone. Sorry for the direct transparency.

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

JetBlue cancelled the flight. We had to rebook on another airline.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

Frontier is good until they cancel your flight. Way too many cancellations.

I know Frontier is a “no-frills” airline. I understand the concept. However, I jumped on some tickets for our family vacation, expecting to play a bit of a game to figure out the family bags and not over spend. In the end, I got the short end of this deal by far. 1. I did not expect them to charge the baggage fee for each direction. It makes the fee look high-ish at a glance, but reasonable. Then when you get to checkout and realize you have to pay it twice to come home with your luggage, it becomes ridiculous. 2. The low checked bag weight limit. I am used to packing a 50lb bag with my preferred airline. Frontier’s artificially low 40lb limit more quickly triggers the extra weight fee, which almost DOUBLES the price of the bag if you go over ($79 for the bag/$75 for the next 10 lbs) 3. The fee for a carry-on bag is the same as a checked bag but with a lower size and weight limit. Make it make sense! 4. The seats are terrible. My 2.5 hour flight almost had me losing my mind. I’m 6’3” and my femurs barely fit in the space provided. My knees had to wiggle just right to jam into the crack next to the armrest of the seat in front of me. The cushioning was thin and inadequate. I am tall but I’m not a freak. These seats are unacceptable. 5. I overheard the woman next to me speaking with the gate agent about being charged a $25 fee for not checking in online - she checked in at the airport counter when she arrived. That’s ridiculous. She was old and in a wheelchair. She had a paper boarding pass, and was obviously not tech savvy. She should not be punished for that. 6. They do not have good placement in the terminals. It was always out on the end or down on a subfloor, and we had to walk out on the tarmac almost every time. In Denver. Their home airport! 7. Every time I loaded a new page on the website while buying my tickets or my bags, it was constantly trying to upsell me on some esoteric bundle. Like, a pop-up every time. Very annoying. 8. No screens in the boarding area (at least where we were) to confirm you’re in the right place. Just static gate number signs. I am sure these are standard practices for Frontier, and I should have read more about them before I purchased tickets, but as a result of this single round trip, I do not plan to ever use this cut-rate airline again. I would rather pay the normal amount for a ticket and be treated like a customer instead of a mark.

Our flight was delayed 2 hours and when they changed the the time to 1 hour I wasn't alerted and when I checked the gate the plane was still there but they already shut the doors so I had to buy another flight.

Great except upon arrival it took them a long time to open the doors

Frontier feels like a family I Worked for Eastern Airlines back in the day and I felt the family vibe that I had then. Thank you

Terrible. Delayed my family flight for several hours affecting family plans

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Tiny seats, no entertainment, no amenities, delays, they charge for carry on and their allowed personal item is smaller than in other airlines.

The seats are tiny and they don’t recline. The planes are dirty and very small. You have to pay for carry on and even the personal item that you’re allowed is smaller than with other airlines. Flights are usually delayed and there’s no screens or any amenities or entertainment.

Flight was delayed but it was very smooth. Crew was very nice. Seats are uncomfortable but ok.

Everything you need to know for your flight to Caribbean

Cabin class types available on flights to Caribbean