$69 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 11/10. 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

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
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Cheap Flights to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$206
Santo Domingo
Santo Domingononstop$208
Montego Bay
Montego Baynonstop$213
Nassau
Nassaunonstop$256
Kingston
Kingstonnonstop$244
Providenciales
Providencialesnonstop$300
Port of Spain
Port of Spain1 stop$277
Bridgetown
Bridgetown1 stop$331
Willemstad
Willemstad1 stop$303
St. John's
St. John'snonstop$305
Puerto Plata
Puerto Platanonstop$323
Aguadilla
Aguadillanonstop$148
Punta Cana
Punta Cananonstop$206
Santo Domingo
Santo Domingononstop$208
Montego Bay
Montego Baynonstop$213
Nassau
Nassaunonstop$256
Kingston
Kingstonnonstop$244
Providenciales
Providencialesnonstop$300
Port of Spain
Port of Spain1 stop$277
Bridgetown
Bridgetown1 stop$331
Willemstad
Willemstad1 stop$303
St. John's
St. John'snonstop$305
Puerto Plata
Puerto Platanonstop$323
Aguadilla
Aguadillanonstop$148

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

Mon, Nov 17 - Fri, Nov 21
Frontier Logo
6:00 am - 4:10 pmJFK-SJU
9h 10m1 stop
Frontier Logo
7:11 am - 10:05 amSJU-JFK
3h 54mnonstop
$129Frontier
Find Deal
Mon, Nov 17 - Thu, Nov 20
Frontier Logo
1:00 pm - 5:54 pmJFK-SJU
3h 54mnonstop
Frontier Logo
7:11 am - 10:05 amSJU-JFK
3h 54mnonstop
$130Frontier
Find Deal
Mon, Mar 2 - Thu, Mar 5
JetBlue Logo
8:05 am - 1:00 pmEWR-SJU
3h 55mnonstop
JetBlue Logo
2:05 pm - 5:28 pmSJU-EWR
4h 23mnonstop
$154JetBlue
Find Deal
Wed, Feb 25 - Fri, Mar 6
JetBlue Logo
6:40 pm - 11:47 pmJFK-SJU
4h 07mnonstop
JetBlue Logo
1:59 am - 5:00 amSJU-JFK
4h 01mnonstop
$174JetBlue
Find Deal
Mon, Dec 8 - Sun, Dec 21
American Airlines Logo
6:29 pm - 10:09 amJFK-SJU
14h 40m1 stop
American Airlines Logo
7:00 am - 2:49 pmSJU-JFK
8h 49m2 stops
$185American Airlines
Find Deal
Sat, Jan 31 - Tue, Feb 3
United Airlines Logo
7:37 pm - 12:36 amEWR-SJU
3h 59mnonstop
United Airlines Logo
7:35 pm - 10:53 pmSJU-EWR
4h 18mnonstop
$186United Airlines
Find Deal
Sat, Dec 6 - Tue, Dec 16
United Airlines Logo
7:37 pm - 12:36 amEWR-SJU
3h 59mnonstop
United Airlines Logo
7:35 pm - 10:53 pmSJU-EWR
4h 18mnonstop
$193United Airlines
Find Deal
Sat, Nov 1 - Wed, Nov 5
American Airlines Logo
1:15 pm - 9:14 pmLGA-SJU
7h 59m1 stop
American Airlines Logo
5:59 pm - 11:21 pmSJU-LGA
6h 22m1 stop
$215American Airlines
Find Deal
Mon, Jan 5 - Fri, Jan 16
Delta Logo
11:25 am - 4:21 pmJFK-PUJ
3h 56mnonstop
Delta Logo
5:46 pm - 8:59 pmPUJ-JFK
4h 13mnonstop
$308Delta
Find Deal
Mon, Oct 27 - Fri, Oct 31
Delta Logo
8:30 am - 12:28 pmJFK-PUJ
3h 58mnonstop
Delta Logo
1:53 pm - 5:59 pmPUJ-JFK
4h 06mnonstop
$311Delta
Find Deal
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 Nassau, at $99 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 $120.

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 $367 on average. The cheapest price found on KAYAK in the last 2 weeks was $65 for the route Tampa (TPA) to Montego Bay (MBJ). The most popular routes on KAYAK are Orlando to Oranjestad which costs $410 on average, and Tampa to Nassau, which costs $439 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 September, when tickets cost $277 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $463 and $452 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Which is the cheapest airport to fly into in Caribbean Islands?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Caribbean Islands is Ponce Mercedita Airport (PSE), with an average flight price of $150.

Good to know

Low seasonSeptember
Cheapest flight$69
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Newark Liberty Airport 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 
Verified travelerFlew with FrontierRDU-SJUMay 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 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.
Maria AlejandraFlew with FrontierJFK-SJUAug 2024
Buy some food and beverage for that 4 hours trip. And download some movies in Netflix
Verified travelerFlew with Spirit AirlinesFLL-KINApr 2024
Check in very early Eat a complete meal before flying Don't be overweight
Verified travelerFlew with United AirlinesEWR-SDQApr 2024
Early check in online, get on time for the flight
KarenFlew with Spirit AirlinesFLL-SJUJan 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 AirlinesTPA-SJUFeb 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 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 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 $469. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $531 on average.

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

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $388 on average. Morning departures are around 100% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands 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 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 $268, from Chicago O'Hare Intl $572, from Newark $592
  • 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 7981 reviews
7.3Food
8.5Crew
7.9Entertainment
7.9Comfort
8.2Boarding
Airline reviews

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

6.0 GoodDavid, Oct 2025JFK - KEF
Read more Delta reviews

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Same as last comment. Food sucks. Quality. Not surprising most people have no clue about nourishment Clearly

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

Friendly and professional flight crew. Aside from departure delay after boarding, easy flight and smooth landing.

Great smooth flight. Had a seating change, but that was an improvement. Thanks United Airways Crew.

The flight attendants were great, I joked with one I can’t remember her name, a blond, really sweet. I thought it was run well very professional. This was great i survived Spirit, I know for which I speak.

My husband and I recently had an unfortunate experience with Lufthansa. At the Philadelphia International airport, the ground staff refused to board us because we didn’t have a current visa stamped on our passports for Frankfurt. We completely understand that this was our mistake. we should have double-checked the visa requirements before our trip. However, the issue that upset us most was how the situation was handled by the staff. They told us they would mark it as “boarding denied due to visa issue”, but instead they recorded it as “no show”. Because of that incorrect entry, our return flight was automatically cancelled as well, which caused additional stress and expense. Mistakes can happen, but we expected more transparency and accuracy from a reputed airline like Lufthansa. It would have made a big difference if the staff had been more careful and considerate in documenting the situation correctly.

Flight was good but there are way to many announcements for credit cards etc.

During booking, I kept trying submitting my payment from the Mexican website and it didn't work. After I had the idea to change it to the Canadian website, it worked but I had to be charged the equivalent of 50 CAD more. I received the clear instruction that I would only be able to check-in at the airport and that it was impossible to select a seat 24 hours before departure, that I had to pay 144 CAD to do so, although not only was I able to check-in 24 hours before departure, but I could have selected my seats for free then. All in all, I almost threw $200 out the window due to misleading information. Besides, the app kept crashing, the information to get to the gate on the app was inaccurate, my gate was switched and I was only informed once in the air (luckily I had noticed the departure pannel), I was not addressed in my language beforehand and even if I tried I was immediately answered in English (which meant the crew understood but didn't want to answer accordingly), there was only one snack & beverage service on my medium haul flight and no beverage service on my short haul flight. To be fair, the planes were comfortable, the crew apart from the language issue was helpful, dynamic and engaging, the plane was clean and the directions were clear and direct. United has a lot of potential to be one of my favourite airlines, but the devil is in the details and a lot of them missed the target.

Flight was timely, relatively comfortable, with decent entertainment and food served. Only problem encountered was with the free messaging which I highly appreciate, but it did not work from iphone to non-iphones.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Disliked having to wait a little longer to disembark from the plan when we landed in London

Typically flights with AA are good. The staff are pleasant, welcoming, and efficient.

A couple ladies from the crew were so rude and nasty. Thought they were mad at having to be there especially if you asked a question. This will make me think twice next time if I book a flight with you.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Flight attendants on this flight were very attentive and friendly

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

Great! I intend to use Spirit for future flights. No complaints .

Seats are not very comfortable, maybe a little more padding for a 2hr plus flight

Very sad about what Spirit has become, because the flights I had with them were delayed between an hour and a half and two, terrible service

Vegas is such a quick flight that amenities aren’t the important part, in my opinion. Just get me there efficiently and safely, and that’s exactly what they did!

The flight was severely delayed due to the missing flight attendants.

Absolutely horrible. Usually pay $40-$50 to check luggage in. I tried to check my suitcase in and the price is raised to $70. That's ridiculously greedy c'mon. I had to leave my suitcase with all my clothes and hygiene products and repurchase once i landed in Atlanta. You guys make it really stressful to travel. Don't even want to travel anymore.

They cancelled the flight 3 hours prior departure. Had to spend $400 for a ne way flight with Delta Airlines! Spirit Airlines are not serios!

My luggage didn’t arrive at LAX, so that wasn’t a good experience.

Terrible seat, no in flight entertainment. No complimentary food or drinks. Seats really hurt my back after flying spirit for the day.

Plastic seat really hurt my back. Cannot even recline on the flight. Very hard to sleep on the plane due to terrible seats . Food and drinks were expensive and not very good. There were like 2 open exit rows behind me. My isle was full so I asked flight attendants if I could sit there. They told me it was a safety issue??? I think it more unsafe to have no one sitting there. In case of emergency, you’d want someone there to help.

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.

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