Cheap Flights to Caribbean from $75 (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*
PHLSan JuanAugust 30 to September 6$183
EWRSanto DomingoSeptember 3 to September 30$260
YYZNassauAugust 17 to August 24$281
JFKOranjestadSeptember 1 to September 8$281
MIANassauJuly 30 to August 5$292
PHLSanto DomingoJuly 18 to July 22$322
EWRSantiago de los CaballerosAugust 4 to August 21$370
JFKPiarcoSeptember 17 to September 23$394
YYZPiarcoSeptember 6 to September 16$592
JFKWest EndAugust 31 to September 7$593
LGWKingstonOctober 15 to October 22$799
LHROranjestadSeptember 4 to September 19$987
BKKSan JuanJuly 28 to October 20$1,767
BKKSanto DomingoJuly 27 to August 5$2,095
BKKOranjestadAugust 1 to August 8$2,467
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
EWRSan JuanJuly 5 to July 9$220
FLLNassauJuly 5 to July 16$346
EWRPunta CanaJuly 5 to July 9$406
EWROranjestadJuly 6 to July 10$428
BOSPunta CanaJuly 6 to July 10$429
JFKPunta CanaJuly 5 to July 9$445
BOSPiarcoJuly 5 to July 21$447
EWRMontego BayJuly 6 to July 9$448
JFKMontego BayJuly 5 to July 9$451
JFKPiarcoJuly 5 to July 9$462
YYZKingstonJuly 6 to July 17$495
EWRKingstonJuly 6 to July 11$561
EWRNassauJuly 5 to July 9$588
JFKNassauJuly 5 to July 9$590
PHLSantiago de los CaballerosJuly 5 to July 10$643
*Prices include taxes and fees

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.
8.8/10 Excellent! (1,001 reviews)
"Excellent location."

Reviewed on Jun 28, 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 Aquaventure and Ocean Club Golf Course are located nearby.
8.6/10 Excellent! (1,718 reviews)
"Wonderful staff and beautiful resort style hotel. Amenities are excellent, including pools and restaurants. The only issue was the house keeping always ran later in the day. We would be out and about only to return late in the afternoon and the room still had not been cleaned. That being said, once ..."

Reviewed on Jul 1, 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.
9/10 Wonderful! (1,003 reviews)
"Everything was amazing word can’t describe"

Reviewed on Jun 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 Ocean Club Golf Course are located nearby.
8.8/10 Excellent! (1,384 reviews)
"Perfect hotel for a family holiday."

Reviewed on Jun 30, 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 $155. 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 $155. 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 $155 and $2,467 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.