Cheap Flights to Caribbean from $60 (2025/2026)

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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*
EWRSan JuanMay 21 to May 29$178
JFKSan JuanMay 17 to May 19$188
FLLMontego BayMay 26 to May 29$208
JFKSanto DomingoJune 4 to June 5$287
JFKSanto DomingoJune 4 to June 5$287
LGAMontego BayMay 17 to May 24$295
BOSMontego BayMay 25 to May 29$297
JFKOranjestadMay 18 to May 20$321
EWRSanto DomingoJune 4 to June 24$331
JFKNassauAugust 3 to August 12$340
MIAWest EndJune 14 to June 21$354
EWRMontego BayJune 12 to June 18$358
JFKPiarcoMay 24 to May 31$394
JFKWest EndMay 26 to May 28$758
JFKWest EndMay 26 to May 28$758
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
EWRSan JuanMay 9 to May 11$208
EWRPunta CanaMay 11 to May 17$304
JFKSanto DomingoMay 10 to June 10$341
JFKSanto DomingoMay 10 to June 10$341
EWRSanto DomingoMay 10 to May 13$349
JFKOranjestadMay 10 to May 24$357
JFKSantiago de los CaballerosMay 11 to May 12$362
JFKSantiago de los CaballerosMay 11 to May 12$362
LGAMontego BayMay 10 to May 15$406
EWRSantiago de los CaballerosMay 11 to May 12$413
BOSOranjestadMay 10 to May 17$419
EWRPiarcoMay 9 to May 12$427
EWRPiarcoMay 9 to May 12$427
JFKNassauMay 10 to May 16$510
JFKNassauMay 10 to May 16$510
*Prices include taxes and fees

Best Caribbean Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Montego Bay - Adults Only - All Inclusive
Princess Senses The Mangrove Resort - Adults Only
Princess Grand Jamaica 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
Stay at this 4.5-star 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 Pan American Pier are located nearby.
8.6/10 Excellent! (1,001 reviews)
"El Convento is always a great choice for Old San Juan. Our room this time did have a disagreeable view of the squalid property’s roof which was next door. Management could not move us but were very apologetic and sincere in taking our concerns seriously. We always stay at El Convento."

Reviewed on Apr 27, 2025

Hotel El Convento
British Colonial - Nassau

British Colonial - Nassau

4 out of 5
Number One Bay St, Nassau
Stay at this 4-star beach hotel in Nassau. Enjoy free WiFi, 2 outdoor pools, and 8 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Junkanoo Beach and Aquaventure are located nearby.
8.4/10 Very Good! (1,539 reviews)
"Very enjoyable stay. Kid friendly and the private beach was awesome"

Reviewed on May 2, 2025

British 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
Stay at this 4-star 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 Pan American Pier are located nearby.
8.8/10 Excellent! (913 reviews)
"Very clean, friendly staff, great restaurant on-site, walkable to points of interest"

Reviewed on Apr 30, 2025

Hotel 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
Stay at this 4.5-star 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 Aquaventure and Cabbage Beach are located nearby.
8.8/10 Excellent! (1,327 reviews)
"Great time at The Reef in Atlantis. Highly recommend if you’re looking for something a bit quieter than the Royal Tower."

Reviewed on May 1, 2025

The 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 $91. 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 20 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 May. 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 $91. 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 $91 and $758 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.
What can I expect on a flight to Caribbean?
The duration of your flight and whether you’re flying with a full-service or low-priced airline play a major role. If you’re searching for long-haul flights to Caribbean, drinks, food and entertainment will often be included. Want cheap flights for family vacations? You’ll save with budget carriers. These airlines usually don’t have as many inclusions, so be prepared to pay for food and drinks.
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.