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Find cheap flights to Caribbean from $39

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 6/4. 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
0 bags
Sat 6/15
Sat 6/22

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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 Cana1 stop$165
Montego Bay
Montego Baynonstop$199
Santo Domingo
Santo Domingononstop$165
Oranjestad
Oranjestad2 stops$257
Nassau
Nassaunonstop$228
Kingston
Kingstonnonstop$268
Simpson Bay
Simpson Baynonstop$174
Providenciales
Providencialesnonstop$280
Port of Spain
Port of Spain1 stop$203
Bridgetown
Bridgetown1 stop$217
George Town
George Townnonstop$296
Aguadilla
Aguadillanonstop$134
Willemstad
Willemstad1 stop$353
St. John's
St. John'snonstop$319

Good to know

Low season

September

High season

December

Cheapest flight

$39
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Orlando Airport to San Juan Airport

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 long is the flight to Caribbean?

    An average nonstop flight from the United States to Caribbean takes 3h 56m, covering a distance of 1550 miles. The most popular route is Newark - San Juan with an average flight time of 3h 52m.

  • What is the cheapest flight to Caribbean?

    The cheapest ticket to Caribbean from the United States found in the last 72 hours was $35 one-way, and $73 round-trip. The most popular route is Newark to San Juan Luis Munoz Marin Intl and the cheapest round-trip airline ticket found on this route in the last 72 hours was $133.

  • Which airlines fly to Caribbean?

    JetBlue, Qatar Airways & Delta fly the most frequently from the United States to Caribbean. The most popular route is from New York to San Juan, and Air Canada, United Airlines and JetBlue fly this route the most.

  • What are the most popular destinations in Caribbean?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (28% of total searches to Caribbean). The next most popular destinations are Santo Domingo (20%) and Montego Bay (16%). Searches for flights to Santiago de los Caballeros (12%), to Oranjestad (12%) and to Nassau (4%) are also popular.

  • How does KAYAK’s flight Price Forecast tool help me choose the right time to buy?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a given destination and date is likely to change within 7 days, so travelers know whether to wait or book now.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • 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.
See more tips

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 10673 reviews
7.4Food
8.2Boarding
8.6Crew
8.0Entertainment
7.9Comfort
Airline reviews

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

4.0 OkayReginald, May 2024MCI - LGA
Read more about Delta reviews

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

The plane was FREEZING SEATS UNCOMFORTABLE Otherwise smooth Thank you

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

Delayed departure. Delayed after landing pulling into gate. Delay due to sky bridge malfunction

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

at the time for boarding the lady just call Group A and no other goups and everybody from A to F go inside without the right turn,and when we get in theres no more spsce for carry on , the ones that get in at not correct group from the back occupy our space !!!!! a mess !!!!

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

I had back trouble prior to my flight and everyone was great about helping me.

Jetblue needs to improve on Onboarding as it seems to always be behind on departing. It never leaves on time. I would recommend to have an earlier Onboarding in order to leave on time and respect your customers time as well.

Not a fan of the diagonal partially enclosed business class seats or how they have to be converted to beds manually by crew. I prefer more isolation and user control for switching to lie flat.

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

We ended up with seats in the very back. So they did not recline. Have no idea why, we reserved and checked in very early. The isles were very narrow and the seats had very little leg room. But they did give us water, and a snack.

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

Check in etc was very good. As for on the plane, it was like flying in a freezer. It was so cold, i have flown for years and never been so cold on a plane. Staff on board said its always cold when flying which is a load of rubbish. They wouldnt put any heating on and now i have the flu because of this .

I’ve had a couple flights this week on United that were delayed by an hour or more

Flight was delayed 2.5 hours - a big deal on an overnight when you plan to sleep.

I feel like they have upgraded the app since I last flew United and I found it to be super helpful. I had stopped flying United unless absolutely necessary and my experience on this trip indicates they have been working hard to improve their services.

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

Tray table was filthy when I sat down. I needed to have someone come clean it because there was food and stains on it WiFi didn’t work after paying for in flight WiFi Food was terrible and was not filling at all Chicken was rubbery Flight attendant had an attitude, interrupted me and wasn’t able to answer basic questions about the food selection such as “does the chicken have red sauce in it”. If your flight attendants are not going to know what is in the meals so we can make an educated decision based on dietary restrictions, they shouldn’t be on the plane. My 1.5 year old niece was sleeping and dropped her binkie. I went on the ground under the chairs looking for it. It was at that time that she came up to me as I’m CLEARLY on all 4s with a flashlight and said “I need to get by”. I said one moment please I’m getting something from under the seat (while my head was literally under the seat). Her reply was “no you need to move now” and proceeded to almost push me out of the way. I looked up and all I saw was her toes under my eyes. When I looked in front of me, her private parts were inches away from my face. I then made a comment “you couldn’t waited 2 seconds?” and her response was, “no I need to use the bathroom”. I understand that and would never want to be the reason someone couldn’t get to the bathroom but I was under the seat. She could’ve gone around the other way instead of harassing me, basically placing her private parts on my head and borderline pushing me out of the way. You don’t pay (especially this much) for this deplorable experience. This was by far the worst experience I have ever had on American. I will be absolutely thinking twice and thrice about flying American Airlines again. I would rather pay more to fly delta because at least I know their WiFi will work and their flight attendants won’t have a terrible attitude for no reason, nor will they act the way this woman did. Unacceptable.

Tray table was filthy when I sat down. I needed to have someone come clean it because there was food and stains on it WiFi didn’t work after paying for in-flight WiFi. Food was terrible and was not filling at all Chicken was rubbery Flight attendant had an attitude, interrupted me and wasn’t able to answer basic questions about the food selection such as “does the chicken have red sauce in it”. If your flight attendants are not going to know what is in the meals so we can make an educated decision based on dietary restrictions, they shouldn’t be on the plane. My 1.5 year old niece was sleeping and dropped her binkie. I went on the ground under the chairs looking for it. It was at that time that she came up to me as I’m CLEARLY on all 4s with a flashlight and said “I need to get by”. I said one moment please I’m getting something from under the seat (while my head was literally under the seat). Her reply was “no you need to move now” and proceeded to almost push me out of the way. I looked up and all I saw was her toes under my eyes. When I looked in front of me, her private parts were inches away from my face. I then made a comment “you couldn’t waited 2 seconds?” and her response was, “no I need to use the bathroom”. I understand that and would never want to be the reason someone couldn’t get to the bathroom but I was under the seat. She could’ve gone around the other way instead of harassing me, basically placing her private parts on my head and borderline pushing me out of the way. You don’t pay that much for this deplorable experience. This was by far the worst experience I have ever had on American. I will be absolutely thinking twice and thrice about flying American Airlines again. I would rather pay more to fly delta because at least I know their WiFi will work and their flight attendants won’t have a shitty attitude for no reason, nor will they act the way this woman did. Unacceptable.

Liked - nothing. Disliked - delayed 35+ min sitting on the plane. Caused me to miss my connection in Charlotte. American Airlines is the worst US Air Carrier company with atrocious customer service.

Worst situation ever! I booked my tickets for this trip on Alaska Airlines. I guess AA is a partner and we flew nonstop from Eugene to PHX on an AA jet. I had to pay for luggage from PHX to EUG. And this was an Alaska Airlines reservation paid for with Alaska airlines credit card! Got to the PHX airport and was not able to check bags because of some weird issue with the AA software. My reservation had to be the-entered by the agent. I will never pick another American Airlines flight on the Alaska Airlines website. While on vacation, I tried to upgrade our seats for the trip home. The request just buffered and never went through. I tried four times and was charged four times on my credit card. The card was charged but the seats were never changed. What a wreck!

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

I like the boarding process, it was fast. The seat doesn’t have a TV for a long flight and food wasn’t served, just snacks.

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

My experience with Spirit was perfect. Did not expect it to be this good

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

Hated it I would not use Kayak or Spirit ever again.

They stuck us with multiple extra fees. I will never fly spirit again

Book Cheap Caribbean Plane Tickets

Recent round-trip flight deals

10/15Tue
nonstopFrontier
2h 57mMCO-SJU
10/29Tue
nonstopFrontier
3h 26mSJU-MCO
$94
10/15Tue
nonstopFrontier
2h 57mMCO-SJU
10/29Tue
nonstopFrontier
3h 26mSJU-MCO
$95
5/29Wed
1 stopSpirit Airlines
5h 25mMCO-SJU
6/5Wed
1 stopSpirit Airlines
12h 16mSJU-MCO
$120
5/28Tue
1 stopSpirit Airlines
14h 45mMCO-SJU
6/1Sat
1 stopSpirit Airlines
4h 57mSJU-MCO
$123
9/6Fri
nonstopDelta
4h 19mJFK-SJU
9/9Mon
nonstopDelta
4h 04mSJU-JFK
$165
6/11Tue
nonstopJetBlue
4h 01mJFK-SJU
6/19Wed
nonstopJetBlue
3h 58mSJU-JFK
$177
8/20Tue
1 stopAmerican Airlines
17h 11mJFK-SJU
8/27Tue
1 stopAmerican Airlines
14h 22mSJU-JFK
$183
7/17Wed
1 stopAmerican Airlines
16h 36mJFK-SJU
7/23Tue
1 stopAmerican Airlines
12h 59mSJU-JFK
$185
6/14Fri
nonstopJetBlue
2h 56mMCO-SJU
6/21Fri
nonstopJetBlue
3h 15mSJU-MCO
$193
9/6Fri
1 stopDelta
11h 59mJFK-SJU
9/10Tue
nonstopDelta
4h 04mSJU-JFK
$235

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Recent one-way flight deals

6/4Tue
1 stopSpirit Airlines
13h 04mMCO-SJU
$39
6/4Tue
1 stopSpirit Airlines
4h 28mMCO-SJU
$47
9/22Sun
nonstopJetBlue
2h 49mMCO-SJU
$87
6/19Wed
nonstopJetBlue
4h 07mJFK-SJU
$89
6/16Sun
1 stopAmerican Airlines
9h 19mJFK-SJU
$93
6/16Sun
1 stopAmerican Airlines
9h 19mJFK-SJU
$95
5/26Sun
nonstopDelta
3h 56mJFK-STI
$136
9/22Sun
1 stopDelta
6h 27mMCO-SJU
$137
6/5Wed
nonstopUnited Airlines
3h 55mEWR-PUJ
$174
8/11Sun
1 stopUnited Airlines
15h 25mEWR-PUJ
$178

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Last minute flights to Caribbean

Last minute flight, train and bus deals

5/21Tue
nonstopFrontier
3h 00mMCO-SJU
5/25Sat
nonstopFrontier
3h 17mSJU-MCO
$132
5/21Tue
nonstop
3h 00mMCO-SJU
5/28Tue
multi-stop
14h 09mSJU-MCO
$134
5/21Tue
multi-stopSpirit Airlines
14h 07mEWR-SJU
5/29Wed
nonstopSpirit Airlines
4h 16mSJU-EWR
$152
5/21Tue
multi-stopSpirit Airlines
6h 24mMCO-SJU
5/25Sat
nonstopSpirit Airlines
3h 10mSJU-MCO
$160
5/19Sun
nonstopDelta
4h 06mJFK-SJU
6/20Thu
nonstopDelta
4h 01mSJU-JFK
$250
5/20Mon
multi-stopAmerican Airlines
14h 16mJFK-SJU
5/21Tue
multi-stopAmerican Airlines
16h 04mSJU-JFK
$253
5/20Mon
multi-stopAmerican Airlines
15h 12mEWR-SJU
5/21Tue
multi-stopAmerican Airlines
15h 37mSJU-EWR
$253
5/21Tue
nonstopDelta
3h 56mJFK-STI
6/7Fri
nonstopDelta
4h 01mSTI-JFK
$269
5/20Mon
nonstopJetBlue
4h 01mJFK-SJU
5/31Fri
multi-stopJetBlue
6h 50mSJU-JFK
$284
5/20Mon
nonstopJetBlue
3h 53mJFK-STI
6/5Wed
nonstopJetBlue
3h 39mSTI-JFK
$290

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Flights to Caribbean

Return flight deals:

Caribbean - United States

Cabin classes:

$184
$277
$219
$59

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