$66+ Cheap flights to Caribbean Islands
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights to Caribbean Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Flights to Caribbean Islands in 2026
Find the latest flights to Caribbean Islands in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on January 15, 2026.
Popular in | December |
|---|---|
Cheapest in | March |
Average price | $238 |
Round-trip from | $135 |
One-way from | $66 |
Find flights to Caribbean Islands
Browse one-way and round-trip flights deals to Caribbean Islands on Cheapflights. Flight deals are based on user searches and were last updated on January 15, 2026
Explore Caribbean Islands
Find flight deals to Caribbean Islands
Cheapest flights to Caribbean IslandsExplore the most affordable flight options available to Caribbean Islands. Find the lowest fares based on data from user searches, with prices last updated on January 15, 2026.
Explore the most affordable flight options available to Caribbean Islands. Find the lowest fares based on data from user searches, with prices last updated on January 15, 2026.
This Flightnetwork deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Expedia deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Super.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This CheapOair deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This CheapOair deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This CheapOair deal was found by Cheapflights users on 1/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Kiwi.com deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
Use the filters below to find and compare flights to Caribbean Islands that are best for you.
Fly from
Route
Depart
Return
Price
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Thu 2/19
7:00 pm-11:59 pm
Nonstop3h 59m
San Juan Luis Munoz Marin Intl
Sun 2/22
6:22 pm-9:30 pm
Nonstop4h 08m
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Thu 2/5
9:29 pm-2:24 am
Nonstop3h 55m
San Juan Luis Munoz Marin Intl
Mon 2/9
8:15 am-11:18 am
Nonstop4h 03m
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Sat 2/28
9:44 am-2:42 pm
Nonstop3h 58m
San Juan Luis Munoz Marin Intl
Tue 3/3
5:10 am-8:17 am
Nonstop4h 07m
NewarkSan Juan
EWR - SJU
EWRSJU
Newark
Mon 2/2
7:10 pm-12:16 am
Nonstop4h 06m
San Juan Luis Munoz Marin Intl
Sat 2/14
5:45 am-9:01 am
Nonstop4h 16m
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Sun 3/22
6:50 pm-10:51 pm
Nonstop4h 01m
San Juan Luis Munoz Marin Intl
Wed 3/25
5:01 am-9:08 am
Nonstop4h 07m
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Sun 3/1
10:55 pm-3:51 am
Nonstop3h 56m
San Juan Luis Munoz Marin Intl
Tue 3/17
6:01 am-10:07 am
Nonstop4h 06m
NewarkSan Juan
EWR - SJU
EWRSJU
Newark
Wed 1/28
11:30 am-9:00 pm
1 stop8h 30m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:05 am-5:24 am
Nonstop4h 19m
NewarkSan Juan
EWR - SJU
EWRSJU
Newark
Sat 2/7
7:30 pm-6:11 am
1 stop9h 41m
San Juan Luis Munoz Marin Intl
Tue 2/10
2:05 am-5:24 am
Nonstop4h 19m
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Sat 2/7
7:35 am-12:29 pm
Nonstop3h 54m
San Juan Luis Munoz Marin Intl
Tue 2/10
9:25 am-12:30 pm
Nonstop4h 05m
New YorkSan Juan
LGA - SJU
LGASJU
New York LaGuardia
Thu 2/12
7:40 am-6:49 pm
1 stop10h 09m
San Juan Luis Munoz Marin Intl
Sat 2/14
5:20 am-11:00 am
1 stop6h 40m
Best time to book a flight to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight to Caribbean Islands
How long is the flight to Caribbean Islands?
On average, a flight from New York to Caribbean Islands takes 10 hours 58 minutes. Flights to Caribbean Islands from other popular cities in USA will vary in length. Below are a few examples of popular routes and their flight times.
When is the cheapest time to fly to Caribbean Islands?
Use this chart to determine the cheapest time to fly round-trip from New York to Caribbean Islands. Price data was last updated on January 10, 2026.
Users looking for the lowest fares to Caribbean Islands should consider flying on Tuesday at noon, when prices are typically cheapest. Budget-minded travelers will want to avoid Sunday afternoons, when prices are usually at their highest.
Weekly flight availability to Caribbean Islands
The most flights from New York to Caribbean Islands are scheduled on a Thursday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 on average).
What are the most popular airlines that fly to Caribbean Islands?
The most popular airlines flying from New York to Caribbean Islands are JetBlue, United Airlines and Delta.
What are the cheapest airlines that fly to Caribbean Islands?
The cheapest airlines flying from New York to Caribbean Islands are Frontier, Spirit Airlines and Delta.
Rainfall in Caribbean Islands by month
Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.
Temperature in Caribbean Islands by month
Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated January 15, 2026.
Get a feel of what it's like to fly with Caribbean Airlines, Delta, and United Airlines to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Boy,Oct 2025
YYZ - POS
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Boy,Oct 2025
YYZ - POS
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Boy,Oct 2025
YYZ - POS
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Boy,Oct 2025
YYZ - POS
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Boy,Oct 2025
YYZ - POS
Food
Entertainment
Crew
Overall
Boarding
Comfort
Reviews
Boy,Oct 2025
YYZ - POS