$99 Find Cheap Flights from White Plains to Caribbean - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from White Plains to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$349
Santo Domingo
Santo Domingo2 stops$461
Montego Bay
Montego Bay1 stop$372
Nassau
Nassau1 stop$312
Kingston
Kingston1 stop$513
Providenciales
Providenciales1 stop$397
George Town
George Town1 stop$591
Aguadilla
Aguadilla1 stop$513
St. John's
St. John's2 stops$545
Punta Cana
Punta Cana1 stop$349
Santo Domingo
Santo Domingo2 stops$461
Montego Bay
Montego Bay1 stop$372
Nassau
Nassau1 stop$312
Kingston
Kingston1 stop$513
Providenciales
Providenciales1 stop$397
George Town
George Town1 stop$591
Aguadilla
Aguadilla1 stop$513
St. John's
St. John's2 stops$545
Booking Insights

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

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

What is the cheapest White Plains to Caribbean flight route?

The cheapest ticket to Caribbean from White Plains found in the last 5 days was to San Juan, at $318 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 $318.

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

The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost $468 on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $468.

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

No, with an average price for the route of $495, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from White Plains to Caribbean is October, when tickets cost $346 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $577 and $556 respectively.

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

When flying from White Plains to Caribbean, you should consider leaving on a Monday and avoid Sundays if you are looking for the best rates. For your return to White Plains, you’ll find the best rates on Tuesdays and the most expensive ones on Wednesdays.

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

To get a below average price on the flight from White Plains to Caribbean, 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

September

Cheapest flight

$99
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from White Plains to Nassau

FAQs - booking Caribbean flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from White Plains 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 White Plains 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 White Plains 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 White Plains 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 White Plains to Caribbean 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 per day?

    There is a maximum of 1 nonstop flight a day that takes off from White Plains and lands in Caribbean, 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

  • 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 $262 one-way - $407 round-trip

Reviews of the top 3 airlines serving from White Plains to Caribbean

 
Need help choosing which airline to fly with from White Plains 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.
7.1
JetBlueOverall score based on 3052 reviews
7.1Entertainment
7.9Crew
7.4Comfort
7.3Boarding
6.6Food
Airline reviews

The flight attendant was snarky and the flight took off very late. I know it was an issue with air traffic control and the runways in Boston, so not really anyone's fault, but very frustrating, I missed an important meeting because of rgr delay. They didn't offer headphones to watch the TV, but luckily I remembered my own and was able to enjoy watching a movie.

4.0 OkayRachel, Oct 2026
Read more JetBlue reviews

The flight attendant was snarky and the flight took off very late. I know it was an issue with air traffic control and the runways in Boston, so not really anyone's fault, but very frustrating, I missed an important meeting because of rgr delay. They didn't offer headphones to watch the TV, but luckily I remembered my own and was able to enjoy watching a movie.

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

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.

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

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

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

The flight left over two hours late. They charged me $180 to bring a carry on. There was an error with the spelling of my name and Frontair agent lied that I would need to pay $200 for her to fix the spelling, and pressured me that if I don't do it quick I would lose the flight. I called back and another agent said it costs $75 to fix. All in all, this company is a complete scam.

I took my first and last flight with FRONTIER. The seats are not able to be reclined so it’s not a very comfortable experience when you take a flight of 3 hours or longer. You must pay for your luggage either carry on or check in, so taking all this in consideration at the end what you think you’re saving your paying in services that should be included. Not a beverage in sight. . You’re seriously better off getting on a proper airline such as Delta, AA, United, etc.

Crew was excellent. Plane was small cramped Airbus A320. Seats were narrow.

They never updated the boarding pass on their apps to show their delay

More options for your flight to Caribbean

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