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Cheap Flights from White Plains to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana2 stops$335
Santo Domingo
Santo Domingo2 stops$325
Montego Bay
Montego Bay1 stop$417
Nassau
Nassau1 stop$306
Kingston
Kingston2 stops$513
Providenciales
Providenciales2 stops$431
George Town
George Town2 stops$500
Aguadilla
Aguadilla1 stop$653
St. John's
St. John's2 stops$581
Punta Cana
Punta Cana2 stops$335
Santo Domingo
Santo Domingo2 stops$325
Montego Bay
Montego Bay1 stop$417
Nassau
Nassau1 stop$306
Kingston
Kingston2 stops$513
Providenciales
Providenciales2 stops$431
George Town
George Town2 stops$500
Aguadilla
Aguadilla1 stop$653
St. John's
St. John's2 stops$581
Booking Insights

KAYAK's insights & trends for White Plains to Caribbean Islands flights

Get data-powered insights and trends into flights from White Plains to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest White Plains to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from White Plains found in the last 5 days was to San Juan, at $298 round-trip. The most popular route is from White Plains (HPN) 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 $298.

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 morning, when round-trip flights cost $471 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $471.

Can I save money by flying with a layover from White Plains to Caribbean Islands?

No, with an average price for the route of $526, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from White Plains to Caribbean Islands?

The cheapest month for flights from White Plains to Caribbean Islands is June, when tickets cost $0 (return) on average. On the other hand, the most expensive months are September and December, when the average cost of round-trip tickets is $1,134 and $866 respectively.

What’s the cheapest day of the week to fly from White Plains to Caribbean Islands?

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Monday and more expensive on a Sunday. On your return trip to White Plains, you should consider flying back on a Tuesday, and avoid Wednesdays for better deals.

How far in advance should I book a flight from White Plains to Caribbean Islands?

To get a below average price on the flight from White Plains to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low season

October
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly and prices are also 34% lower on average.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from White Plains 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 White Plains to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from White Plains to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from White Plains 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 White Plains 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 White Plains 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 White Plains 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 White Plains to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between White Plains and Caribbean Islands per day?

    There is a maximum of 1 nonstop flight a day that takes off from White Plains and lands in Caribbean Islands, with an average flight time of 3h 53m. The most common departure time is 7:00 am and most flights take off in the morning. Each week, there are 5 flights.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from White Plains to the following destinations at these prices or less: San Juan $222 one-way - $387 round-trip

Reviews of the top airlines flying from White Plains to Caribbean Islands

 
Need help choosing which airline to fly with from White Plains 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.
7.1
JetBlueOverall score based on 3067 reviews
7.3Boarding
7.1Entertainment
7.9Crew
7.4Comfort
6.6Food
Airline reviews

The plane was FREEZING COLD. Like I was wishing I'd brought gloves. Is this how JetBlue sells more blankets? Other than that, all fine. Crew just as nice as usual. A flight attendant asked (who? The pilot?) to have the air turned down for a great number of passengers who were as cold as I was. They (again -- who is "they") did not.

6.0 GoodAnonymous, Oct 2026
Read more JetBlue reviews

The plane was FREEZING COLD. Like I was wishing I'd brought gloves. Is this how JetBlue sells more blankets? Other than that, all fine. Crew just as nice as usual. A flight attendant asked (who? The pilot?) to have the air turned down for a great number of passengers who were as cold as I was. They (again -- who is "they") did not.

Flight was fine, but I was annoyed to have to pay for luggage again. We had paid for our luggage on our first two connecting flights with SATA Azores Airlines, but had to pay for luggage again with JetBlue at JFK airport. For one trip we paid over $500 for two suitcases to travel from Azores to San Francisco.

Uncomfortable seat. No help for my disability. Staff refused to help me put my carry-on in the overhead bin. So I had to check the bag.

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.

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

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

Communication since no reason or explanation was given for 3 hrs delay

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

No WiFi No TV Bag of chips I guess it could be worse.

The delays were not communicated well at all. I was in the airport for over 9 hours with little knowledge of if I was actually going to reach my destination.

It was OK, but it was delayed about an hour, and my luggage didn't arrive till about an hour and a half after the flight

Another American Airlines flight, another significant delay. At least this one wasn't canceled like many others have been. This time we sat on the runway at LaGuardia for 2.5 hours. By my count that is 7 American flights the last three months that have been delayed 2 hours or more or canceled entirely.

Our trip to Spain turned into a stressful ordeal with cockpit issues and FAA air traffic disruptions. Our American Airlines flight from Raleigh to JFK was delayed nearly four hours, causing us to miss our connections to Madrid and Jerez. We were left stranded in New York with children, even running out of diapers while trying to sort everything out. American refused to cover hotels or rental cars, leaving us to arrange and pay for them ourselves. The delays also disrupted our prepaid rental car reservations in Spain. It was a frustrating and expensive start to a family trip we had spent months planning.

Unfortunately the flight was delayed by almost 2 hours, so I missed an appointment arriving into DFW

Very cold on board it was like having 16hours sitting in a fridge

My experience was excellent for a business trip. I like the smaller jets because everyone gets either a window or aisle seat and the boarding and de-planing goes much faster. I really like the schedule American Airlines has between Atlanta and NY - lots of options. Crews are great and very accommodating. Sometimes the flights are not full and they let people move around once the boarding doors are shut to spread out.

I had ridiculously long body search because I have knee and hip replacements

Their computers were down upon arrival to the airport. They were unable to figure out how to board us. We were delayed over an hour and a half.

Free wifi kept dropping so no inflight entertainment. And only snack option was cookies.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental