Flights To Caribbean - Cheap Flights Starting at CA $147

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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.

Sat, Jan 24 - Sat, Jan 31
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $324 Roundtrip, found 2 hours ago
CA $324
Roundtrip
found 2 hours ago
Select Flair Airlines flight, departing Sat, Jan 24 from Pearson Intl. to Punta Cana Intl., returning Sat, Jan 31, priced at CA $324 found 2 hours ago
Sat, Feb 14 - Thu, Feb 19
YTZ
Billy Bishop Toronto City
NAS
Lynden Pindling Intl.
CA $358 Roundtrip, found 1 hour ago
CA $358
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Sat, Feb 14 from Billy Bishop Toronto City to Lynden Pindling Intl., returning Thu, Feb 19, priced at CA $358 found 1 hour 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, Feb 8 - Thu, Feb 12
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $399 Roundtrip, found 3 days ago
CA $399
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Feb 8 from Pearson Intl. to Luis Munoz Marin Intl., returning Thu, Feb 12, priced at CA $399 found 3 days ago
Mon, Dec 8 - Wed, Dec 24
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $412 Roundtrip, found 23 hours ago
CA $412
Roundtrip
found 23 hours ago
Select WestJet flight, departing Mon, Dec 8 from Pearson Intl. to Queen Beatrix Intl., returning Wed, Dec 24, priced at CA $412 found 23 hours ago
Sun, Dec 7 - Sun, Dec 14
YTZ
Billy Bishop Toronto City
PUJ
Punta Cana Intl.
CA $418 Roundtrip, found 21 hours ago
CA $418
Roundtrip
found 21 hours ago
Select Air Transat flight, departing Sun, Dec 7 from Billy Bishop Toronto City to Punta Cana Intl., returning Sun, Dec 14, priced at CA $418 found 21 hours ago
Sat, Jan 17 - Sat, Jan 24
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $419 Roundtrip, found 1 hour ago
CA $419
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Sat, Jan 17 from Pearson Intl. to Sir Donald Sangster Intl., returning Sat, Jan 24, priced at CA $419 found 1 hour ago
Mon, Apr 6 - Tue, Apr 14
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $430 Roundtrip, found 13 hours ago
CA $430
Roundtrip
found 13 hours ago
Select WestJet flight, departing Mon, Apr 6 from Pearson Intl. to Norman Manley Intl., returning Tue, Apr 14, priced at CA $430 found 13 hours ago
OriginDestinationTravel datesFlights from*
EWRSan JuanFebruary 22 to February 26CA $247
JFKSan JuanJanuary 23 to January 28CA $261
EWROranjestadDecember 13 to December 21CA $340
EWRSanto DomingoMarch 6 to March 15CA $351
EWRSanto DomingoMarch 6 to March 15CA $351
LGAPiarcoDecember 9 to December 16CA $418
JFKOranjestadDecember 9 to January 15CA $423
EWRMontego BayJanuary 9 to January 9CA $431
JFKSanto DomingoDecember 12 to December 15CA $448
LGANassauJanuary 28 to February 3CA $449
JFKNassauMarch 6 to March 14CA $450
JFKMontego BayDecember 10 to December 14CA $507
JFKSantiago de los CaballerosDecember 31 to January 30CA $537
JFKKingstonJanuary 31 to February 6CA $555
JFKPiarcoDecember 19 to January 1CA $563
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKSan JuanNovember 29 to November 30CA $386
JFKSan JuanNovember 29 to November 30CA $386
EWRPunta CanaNovember 30 to December 4CA $460
EWRPunta CanaNovember 30 to December 4CA $460
JFKPunta CanaNovember 30 to December 4CA $478
JFKSanto DomingoNovember 29 to December 2CA $527
JFKSanto DomingoNovember 29 to December 2CA $527
EWRSan JuanNovember 28 to December 2CA $542
JFKSantiago de los CaballerosNovember 28 to December 5CA $641
JFKSantiago de los CaballerosNovember 28 to December 5CA $641
EWRSantiago de los CaballerosNovember 28 to December 5CA $708
EWRSanto DomingoNovember 29 to December 2CA $717
BOSOranjestadNovember 30 to December 6CA $722
JFKMontego BayNovember 28 to December 1CA $729
JFKMontego BayNovember 28 to December 1CA $729
*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 6 - Feb 13

7 night stay

Hamilton (YHM) to Santo Domingo (SDQ)

Air Canada • Roundtrip • Coach
Price was CA $3,748, price is now CA $1,468 per person
CA $1,468
per person
found 1 day ago
Sunset at the Palms Resort - Adults Only - All Inclusive
4.5-star property

Sunset at the Palms Resort - Adults Only - All Inclusive

Jan 19 - Jan 25

6 night stay

Toronto (YTO) to Montego Bay (MBJ)

WestJet • Coach

Montego Bay (MBJ) to Toronto (YTO)

Flair Airlines • Coach
Price was CA $6,627, price is now CA $2,385 per person
CA $2,385
per person
found 1 day ago
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Jan 27 - Feb 3

7 night stay

Toronto (YTO) to Montego Bay (MBJ)

WestJet • Roundtrip • Coach
Price was CA $4,127, price is now CA $1,575 per person
CA $1,575
per person
found 22 hours 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! (1,296 reviews)
Room was great. Pool was extremely small and pretty disgusting, dirty, no towels and even all the seats were gross. Definitely a bummer.

Reviewed on Nov 19, 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 $247. 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 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 $247. 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 $247 and CA $729 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.