Flights To Caribbean - Cheap Flights Starting at CA $177

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How Much Does it Cost To Fly To Caribbean?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

OriginDestinationTravel datesFlights from*
EWRSanto DomingoMay 7 to May 10CA $341
EWRPunta CanaMay 9 to May 16CA $358
LGAMontego BayApril 21 to April 28CA $398
JFKOranjestadJune 3 to June 8CA $405
JFKOranjestadJune 3 to June 8CA $405
EWRMontego BayApril 21 to April 28CA $409
JFKPiarcoJune 22 to July 6CA $448
JFKPiarcoJune 22 to July 6CA $448
JFKSanto DomingoMay 18 to May 20CA $474
JFKMontego BayJune 11 to June 19CA $490
EWRPiarcoMay 8 to May 15CA $493
EWRNassauApril 12 to April 21CA $494
JFKSantiago de los CaballerosMay 18 to June 1CA $551
JFKKingstonJune 1 to June 16CA $626
EWRKingstonMay 2 to May 9CA $680
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
EWRMontego BayMarch 15 to March 19CA $415
EWRMontego BayMarch 15 to March 19CA $415
BOSSanto DomingoMarch 15 to March 19CA $431
EWRSan JuanMarch 15 to March 19CA $662
EWRSan JuanMarch 15 to March 19CA $662
JFKOranjestadMarch 13 to March 17CA $682
JFKSanto DomingoMarch 14 to March 20CA $760
JFKSanto DomingoMarch 14 to March 20CA $760
LGAKingstonMarch 13 to March 20CA $791
JFKPiarcoMarch 15 to March 21CA $847
EWRKingstonMarch 13 to March 20CA $857
JFKKingstonMarch 14 to March 18CA $911
EWRPiarcoMarch 15 to March 21CA $913
JFKMontego BayMarch 15 to March 21CA $1,237
EWROranjestadMarch 13 to March 17CA $1,828
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Silver Creek Resort
Sunset at the Palms Resort - Adults Only - All Inclusive
Coral Costa Caribe Beach Resort - All Inclusive
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Travelers ❤️ These Caribbean 🏨

Hotel El Convento

Hotel El Convento

4.5 out of 5
100 Cristo St San Juan
Book a stay at this luxury hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Condado Beach are located nearby.
9/10 Wonderful! (1,011 reviews)
Perfect location across from the Cathedral. A beautiful historic hotel.

Reviewed on Mar 7, 2026

Opens in a new windowHotel El Convento
British Colonial - Nassau

British Colonial - Nassau

4 out of 5
Number One Bay St Nassau
Book a stay at this beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 6 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Junkanoo Beach and Cable Beach are located nearby.
8.6/10 Excellent! (2,326 reviews)
Clean room,staff are nice. I was supposed to have a room facing the garden, but I didn't see any of that. I only had a view of a parking lot.Nice room tho. Pool 24 hour and private beach wow!

Reviewed on Mar 9, 2026

Opens in a new windowBritish Colonial - Nassau
Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel

4 out of 5
100 Brumbaugh Street San Juan Puerto Rico
Book a stay at this business-friendly hotel in San Juan. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of San Juan and Condado Beach are located nearby.
9/10 Wonderful! (1,564 reviews)
Clean room great air conditioning very friendly staff

Reviewed on Mar 10, 2026

Opens in a new windowHotel Rumbao, a Tribute Portfolio Hotel
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The Reef at Atlantis

The Reef at Atlantis

4.5 out of 5
Paradise Beach Drive Paradise Island New Providence
Book a stay at this luxury resort in Paradise Island. Enjoy free WiFi, a full-service spa, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Junkanoo Beach and Cable Beach are located nearby.
9/10 Wonderful! (1,442 reviews)
Had great time Family of 4 with 2 kids Amazing place to spend time

Reviewed on Mar 9, 2026

Opens in a new windowThe Reef at Atlantis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Caribbean?
Your next vacation doesn't have to make a huge dent in your budget. During the last seven days, the cheapest roundtrip flight to Caribbean cost CA $341. Find a cheap ticket and spend the money you save on cool experiences. This price was available on Travelocity for flights to Caribbean departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Caribbean?
Pack your bags and jet off with any of the 15 airlines that fly to Caribbean. Make a booking with popular air carrier, Sunrise Airways. It has approximately 43 flights per month to Santo Domingo, Caribbean's premier city, so finding a fare that suits should be a snap.
What is the cheapest month to fly to Caribbean?
Spend more money on great adventures rather than airfares by zipping off to Caribbean in August. This is the best-priced month to jet out to this place according to Travelocity's direct return flight demand from January to December last year. Browse through our range of flights and enjoy a change of scenery without emptying your bank account.
How can I check my flight status to Caribbean?
Check for updates on your flight to Caribbean, make changes and much more from our "Trips" customer portal. Found at the top right of our homepage, it's your gateway to viewing your bookings. Just log in or open an account in seconds. Savvy wanderers can also take advantage of the Travelocity app. You'll get real-time trip updates, along with the ability to book hotels, rental cars and activities while you're on the go. If you have friends or family flying with you, it's also a quick way to share travel info with each other.
How do I find the best deals on flights to Caribbean?
It's always good to book ahead of schedule, and if possible, avoid traveling during the busy tourist season. Another great way to save is by hitting the "Flexible dates" box at the top of the page after searching for your flights. This will show you ticket prices for nearby days. In the last seven days, the lowest price for a return flight to Caribbean was CA $341. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Caribbean with Travelocity?
Pack your case and get set to take off with Travelocity. It's our job to find you fantastic deals on cheap flights to Caribbean. Whether you want flexible airfares with plenty of wiggle room or cheap family flights on budget carriers, we've got what you need.
How much is a flight to Caribbean on average?
Plane tickets for roundtrip flights to Caribbean cost between CA $341 and CA $1,828 in the last seven days. The moment you find an incredible deal, lock it in and get ready to set off on the getaway of your dreams with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.