Flights To Caribbean - Cheap Flights Starting at CA $125

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San Juan

Flights
San Juan

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.

Tue, Jan 27 - Sat, Jan 31
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
CA $262 Roundtrip, found 4 days ago
CA $262
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Jan 27 from John F. Kennedy Intl. to Luis Munoz Marin Intl., returning Sat, Jan 31, priced at CA $262 found 4 days ago
Fri, Dec 19 - Wed, Dec 24
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
CA $263 Roundtrip, found 1 day ago
CA $263
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Dec 19 from John F. Kennedy Intl. to Luis Munoz Marin Intl., returning Wed, Dec 24, priced at CA $263 found 1 day ago
Mon, Dec 1 - Fri, Dec 5
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
CA $317 Roundtrip, found 5 days ago
CA $317
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Dec 1 from John F. Kennedy Intl. to Luis Munoz Marin Intl., returning Fri, Dec 5, priced at CA $317 found 5 days ago
Fri, Feb 27 - Thu, Mar 5
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $328 Roundtrip, found 22 hours ago
CA $328
Roundtrip
found 22 hours ago
Select Arajet flight, departing Fri, Feb 27 from Pearson Intl. to Punta Cana Intl., returning Thu, Mar 5, priced at CA $328 found 22 hours ago
Sun, Nov 30 - Sat, Dec 6
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $360 Roundtrip, just found
CA $360
Roundtrip
just found
Select WestJet flight, departing Sun, Nov 30 from Pearson Intl. to Lynden Pindling Intl., returning Sat, Dec 6, priced at CA $360 just found
Sun, Dec 7 - Fri, Dec 12
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $372 Roundtrip, found 1 day ago
CA $372
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Dec 7 from Pearson Intl. to Luis Munoz Marin Intl., returning Fri, Dec 12, priced at CA $372 found 1 day ago
Mon, Jan 19 - Tue, Jan 27
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
CA $389 Roundtrip, found 20 hours ago
CA $389
Roundtrip
found 20 hours ago
Select Delta flight, departing Mon, Jan 19 from John F. Kennedy Intl. to Luis Munoz Marin Intl., returning Tue, Jan 27, priced at CA $389 found 20 hours ago
Mon, Jan 5 - Fri, Jan 16
JFK
John F. Kennedy Intl.
PUJ
Punta Cana Intl.
CA $397 Roundtrip, found 6 days ago
CA $397
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Jan 5 from John F. Kennedy Intl. to Punta Cana Intl., returning Fri, Jan 16, priced at CA $397 found 6 days ago
Fri, May 8 - Tue, May 12
JFK
John F. Kennedy Intl.
POS
Piarco Intl.
CA $416 Roundtrip, found 4 hours ago
CA $416
Roundtrip
found 4 hours ago
Select Caribbean Airlines flight, departing Fri, May 8 from John F. Kennedy Intl. to Piarco Intl., returning Tue, May 12, priced at CA $416 found 4 hours ago
Sun, Dec 7 - Thu, Dec 11
JFK
John F. Kennedy Intl.
AUA
Queen Beatrix Intl.
CA $422 Roundtrip, found 6 days ago
CA $422
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sun, Dec 7 from John F. Kennedy Intl. to Queen Beatrix Intl., returning Thu, Dec 11, priced at CA $422 found 6 days ago
Mon, Dec 1 - Sun, Dec 7
JFK
John F. Kennedy Intl.
SDQ
Las Americas Intl.
CA $448 Roundtrip, found 6 days ago
CA $448
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Dec 1 from John F. Kennedy Intl. to Las Americas Intl., returning Sun, Dec 7, priced at CA $448 found 6 days ago
OriginDestinationTravel datesFlights from*
EWRSanto DomingoJanuary 21 to January 28CA $347
EWRSanto DomingoJanuary 21 to January 28CA $347
EWRPunta CanaFebruary 18 to March 8CA $350
JFKPunta CanaJanuary 11 to January 18CA $398
LGAMontego BayJanuary 8 to January 15CA $437
JFKSanto DomingoDecember 12 to December 15CA $448
JFKSantiago de los CaballerosJanuary 19 to January 28CA $450
JFKSantiago de los CaballerosJanuary 19 to January 28CA $450
EWRSantiago de los CaballerosJanuary 27 to February 1CA $450
JFKNassauMarch 6 to March 14CA $450
JFKNassauMarch 6 to March 14CA $450
EWRNassauDecember 12 to December 16CA $508
LGAPiarcoJanuary 7 to January 20CA $595
JFKPiarcoMarch 12 to March 21CA $632
EWRPiarcoFebruary 6 to February 16CA $690
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LGASanto DomingoDecember 6 to December 9CA $397
EWRSanto DomingoDecember 6 to December 9CA $418
JFKOranjestadDecember 7 to December 11CA $422
JFKSanto DomingoDecember 7 to December 11CA $448
JFKNassauDecember 7 to December 13CA $466
JFKNassauDecember 7 to December 13CA $466
EWROranjestadDecember 7 to December 11CA $470
EWRMontego BayDecember 7 to December 16CA $569
EWRPunta CanaDecember 5 to December 7CA $572
EWRPunta CanaDecember 5 to December 7CA $572
LGAPiarcoDecember 6 to December 16CA $584
JFKPunta CanaDecember 5 to December 7CA $602
EWRNassauDecember 5 to December 8CA $725
JFKMontego BayDecember 7 to January 2CA $1,144
JFKKingstonDecember 7 to January 2CA $1,168
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Coral Costa Caribe Beach Resort - All Inclusive
4.0-star property

Coral Costa Caribe Beach Resort - All Inclusive

Feb 5 - Feb 12

7 night stay

Ottawa (YOW) to Santo Domingo (SDQ)

Air Canada • Roundtrip • Coach
Price was CA $3,708, price is now CA $1,526 per person
CA $1,526
per person
found 1 day ago
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Feb 14 - Feb 21

7 night stay

Toronto (YYZ) to Montego Bay (MBJ)

Flair Airlines • Roundtrip • Coach
Price was CA $4,166, price is now CA $1,615 per person
CA $1,615
per person
found 1 day ago
Ocho Rios Villa at The Palms
3.0-star property

Ocho Rios Villa at The Palms

Feb 7 - Feb 14

7 night stay

Toronto (YYZ) to Montego Bay (MBJ)

Flair Airlines • Coach

Montego Bay (MBJ) to Toronto (YYZ)

United • Coach
Price was CA $3,933, price is now CA $1,629 per person
CA $1,629
per person
found 1 day ago
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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 Pan American Pier are located nearby.
8.8/10 Excellent! (1,000 reviews)
The room was very clean staff was very friendly enjoyed my stay and will go back again 😊

Reviewed on Nov 15, 2025

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 8 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cable Beach and Pirates of Nassau Museum are located nearby.
8.6/10 Excellent! (2,044 reviews)
What stood out was the architectural structure of the hotel and how clean it was upon arrival, from the hotel grounds, lobby, restaurants, hallways, and rooms.

Reviewed on Nov 21, 2025

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 Pan American Pier are located nearby.
9/10 Wonderful! (1,319 reviews)
Amazing staff and room

Reviewed on Nov 27, 2025

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 Cable Beach and Aquaventure are located nearby.
8.8/10 Excellent! (1,434 reviews)
Amazing b

Reviewed on Nov 24, 2025

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 $262. 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 January. 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 $262. 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 $262 and CA $1,168 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.

Destinations in Caribbean

*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.