$136 Find Cheap Flights from White Plains to Caribbean - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from White Plains to Caribbean departing on 8/24. 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.
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Cheap Flights from White Plains to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$448
Santo Domingo
Santo Domingo1 stop$499
Montego Bay
Montego Bay1 stop$344
Oranjestad
Oranjestad1 stop$417
Nassau
Nassau1 stop$419
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$397
Providenciales
Providenciales1 stop$423
Port of Spain
Port of Spain2 stops$774
George Town
George Town1 stop$357
Willemstad
Willemstad2 stops$845
Aguadilla
Aguadilla1 stop$438
St. John's
St. John's2 stops$575
Punta Cana
Punta Cana1 stop$448
Santo Domingo
Santo Domingo1 stop$499
Montego Bay
Montego Bay1 stop$344
Oranjestad
Oranjestad1 stop$417
Nassau
Nassau1 stop$419
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay1 stop$397
Providenciales
Providenciales1 stop$423
Port of Spain
Port of Spain2 stops$774
George Town
George Town1 stop$357
Willemstad
Willemstad2 stops$845
Aguadilla
Aguadilla1 stop$438
St. John's
St. John's2 stops$575

Book Cheap White Plains to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from White Plains to Caribbean 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 from White Plains to Caribbean

Mon, Oct 26 - Fri, Oct 30
JetBlue Logo
7:30 am - 11:18 am
HPN
-
SJU
3h 48mnonstop
JetBlue Logo
5:30 pm - 9:35 pm
SJU
-
HPN
4h 05mnonstop
$312JetBlue
Sat, Sep 19 - Sun, Sep 27
JetBlue Logo
7:30 am - 11:29 am
HPN
-
SJU
3h 59mnonstop
JetBlue Logo
5:15 pm - 9:30 pm
SJU
-
HPN
4h 15mnonstop
$315JetBlue
Mon, Oct 26 - Fri, Oct 30
American Airlines Logo
5:25 pm - 9:46 am
HPN
-
SJU
16h 21m
2 stops
American Airlines Logo
6:20 am - 11:29 pm
SJU
-
HPN
17h 09m
2 stops
$336American Airlines
Wed, Sep 9 - Thu, Sep 17
American Airlines Logo
7:40 am - 2:50 pm
HPN
-
SJU
7h 10m
1 stop
American Airlines Logo
2:22 pm - 11:26 pm
SJU
-
HPN
9h 04m
2 stops
$341American Airlines
Sat, Sep 19 - Sat, Sep 26
Delta Logo
6:00 am - 4:49 pm
HPN
-
SJU
10h 49m
1 stop
Delta Logo
7:00 am - 6:00 pm
SJU
-
HPN
11h 00m
1 stop
$342Delta
Tue, Sep 8 - Fri, Sep 18
JetBlue Logo
8:30 am - 5:33 pm
HPN
-
MBJ
10h 03m
1 stop
JetBlue Logo
1:15 pm - 10:57 pm
MBJ
-
HPN
8h 42m
1 stop
$344JetBlue
Sat, Aug 29 - Wed, Sep 2
JetBlue Logo
8:00 am - 11:51 am
HPN
-
SJU
3h 51mnonstop
JetBlue Logo
5:44 pm - 9:45 pm
SJU
-
HPN
4h 01mnonstop
$345JetBlue
Tue, Nov 3 - Tue, Nov 17
American Airlines Logo
11:25 am - 11:56 pm
HPN
-
SJU
11h 31m
2 stops
American Airlines Logo
7:40 am - 8:09 pm
SJU
-
HPN
13h 29m
2 stops
$346American Airlines
Mon, Aug 24 - Sat, Aug 29
Delta Logo
6:00 am - 3:34 pm
HPN
-
MBJ
10h 34m
1 stop
Delta Logo
4:59 pm - 9:49 am
MBJ
-
HPN
15h 50m
1 stop
$352Delta
Wed, Sep 23 - Mon, Sep 28
Multiple Airlines Logo
9:00 pm - 10:20 am
HPN
-
CUR
37h 20m
2 stops
Multiple Airlines Logo
11:35 am - 10:57 pm
CUR
-
HPN
35h 22m
2 stops
$877Multiple Airlines
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from White Plains found in the last 5 days was to San Juan, at $375 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 $375.

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

The average price for all round-trip flights from White Plains to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost $434 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 $434.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $470, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from White Plains to Caribbean, 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 White Plains to Caribbean is October, when tickets cost $238 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $591 and $533 respectively.

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

The average price of all round-trip flights from White Plains to Caribbean clicked on KAYAK for each day over the last 12 months.

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

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from White Plains to Caribbean, 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 White Plains to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low season

May

Cheapest flight

$136
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 9% 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.

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 $197 one-way - $427 round-trip

Reviews of the top 4 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.
7.8
DeltaOverall score based on 8475 reviews
8.5Crew
7.2Food
7.8Entertainment
7.8Comfort
8.1Boarding
Airline reviews

Flight delayed due to ground hold. Republic airways did a great job.

6.0 GoodSohail, Jul 2026
LGA - DCA
Read more Delta reviews

Flight delayed due to ground hold. Republic airways did a great job.

Our flight was delayed multiple times and then canceled at almost 1 in the morning. We are a family of 7, traveling with 5 young children. When the flight we were supposed to fly on finally arrived after waiting all day after an international flight into JFK we were informed our flight was in need of a copilot and once they located one we would take off. Then our flight was cancelled because the copilot was over his hours and they couldn't locate another. They knew before taking off from the previous location that the copilot would be unable to fly. They could have communicated the cancellation of the flight hours in advance. Once they cancelled and the pilot and copilot got off the flight, they joked about it. While there are understandably limits on flight time for pilots, they can still handle the situation in a professional manner. The late cancellation resulted in angry passengers that required police intervention in the airport. It also occurred so late and included other delta flights that after trying 15 different hotels, we were unable to secure a hotel room, they were all booked. No rental cars were available in the area either. We ended up staying in the airport with the 5 children. We made it home after 54 hours of travel with maybe 2 hours of sleep. Our luggage was lost and had to be claimed at the airport at our final destination. This was the worst trip I have ever taken and the worst airport I have ever spent time in. I met two individuals in the airport that were kind and helpful; Tonya Maingot Williams from the can we hel desk that worked to help get us rebooked and home, as well as provide us with care bags for our extended stay in the airport. The other individual was Danielle from Buffalo Wild Wings that was so very kind when we found a place to take our family we were traveling with to eat, all 11 of us and we were able to sit down together to enjoy a meal during such a stressful time.

FA was a bit strange and dodgy not very characteristic of Delta

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

The boarding announcement was hard to understand and I almost missed getting on board because of the garbled announcement.

Crew and agents misguiding on tight connections, and lack of connecting crew looking for inbound planes. A very avoidable missed connection as a result.

I don’t like the music section but I believe it was a cost decision. I changed my flight last minute due to work issues and had to sit way in the back. The seats were way closer together than I would have preferred.

Our particular exceptional experience was with Johnny at JFK at check in. He was the kindest, most accommodating agent I’ve ever encountered taking extra steps to help my husband and I with our extra baggage. I hope that he knows how much he positively affected our trip.

The flight attendant was very polite and attentive. The food was good.

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

Pilots were fantastic - super smooth. First Class flight attendant was very attentive. Main Cabin flight attendant should try to smooth the rough edges of her voice - very shrill / punitive. Hurt my ears just to listen to her. Recognize they have a (tough) job to do - but tone over speakers needs to be less like scolding a 5 year old.

Maybe focus more on delivering a good product vs selling me a damn credit card

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 flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

see my previous response about being kicked off the flight and having to fly the next day, ruining a planned vacation tour.

It was a smooth flight and the pilot was very pleasant

Flight was cancelled, no support at JFK even though it is their main hub.. wait times on the phone was very long

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.

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

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports