$142 Find Cheap Flights from White Plains to Caribbean Islands - Compare and Save

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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 Cana1 stop$343
Santo Domingo
Santo Domingo1 stop$449
Montego Bay
Montego Bay1 stop$316
Nassau
Nassau2 stops$335
Kingston
Kingston2 stops$478
Providenciales
Providenciales2 stops$460
George Town
George Town1 stop$435
Aguadilla
Aguadilla1 stop$527
St. John's
St. John's2 stops$527
Punta Cana
Punta Cana1 stop$343
Santo Domingo
Santo Domingo1 stop$449
Montego Bay
Montego Bay1 stop$316
Nassau
Nassau2 stops$335
Kingston
Kingston2 stops$478
Providenciales
Providenciales2 stops$460
George Town
George Town1 stop$435
Aguadilla
Aguadilla1 stop$527
St. John's
St. John's2 stops$527
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 $301 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 $301.

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 $443 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 $443.

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

No, with an average price for the route of $480, 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 Friday, and avoid Mondays 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 3 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low season

September

Cheapest flight

$142
Best time to beat the crowds but there is an average 38% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from White Plains to Montego Bay

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 59m. 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 $232 one-way - $336 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
American AirlinesOverall score based on 12046 reviews
6.8Entertainment
7.2Comfort
7.9Crew
7.5Boarding
6.4Food
Airline reviews

Old dirty plane but great lie flat seats in business class

10.0 ExcellentChristian, Sep 2026
Read more American Airlines reviews

Old dirty plane but great lie flat seats in business class

Communication not good, too many changes. Three flights were cancelled due to weather and the options were not acceptable. I had to cancel my Canada portion of the trip.

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

Aa cancelled my flight where I was in first class seat 4B. They auto rebooked me on another flight, did not give me a seat assignment until at the gate. Where I got seat 29f, for a 4 hr flight. No accommodation at all for my first class ticket. Left 3 hrs late as well.

It was delayed 5 hours due weather and your app should be rebuilt or disabled. I could not change my original flight on delta so I did it through the delta app. Then rebooked on American once delta cancelled all flights from LGA to PIT on 8/27. American Airlines was fine once the flight took off 5 hours later. I wish my company would find a better provider than kayak.

DCA-LAX No screen on a 5 hour flight (almost) no food for sale on a 5 hour flight (practically) no wifi coverage or speed on a 5 hour flight I should have gotten my money back, shame on American

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

A crew member's attitude towards a couple passengers who couldn't speak English was rude. Just because they didn't understand what the passenger said, they were not given any snack.

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.

The plane was filthy and worn - the seat pockets were stuffed with tattered food and torn pamphlets. The cleaning crew that came on as we were deboarding were grabbing handfulls of trash and perfunctorily wiping down tables with dishrags. It's been a while since I flew Jetblue and it used to be a great experience. After this flight I will avoid flying Jetblue again if there is any alternative.

JFK is the worst airport and JetBlue is the worst airline

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.

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.

More options for your flight to Caribbean Islands

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