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 10 - Sat, Jan 17
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $327 Roundtrip, found 3 hours ago
CA $327
Roundtrip
found 3 hours ago
Select Arajet flight, departing Sat, Jan 10 from Pearson Intl. to Punta Cana Intl., returning Sat, Jan 17, priced at CA $327 found 3 hours ago
Sun, Nov 30 - Mon, Dec 1
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $360 Roundtrip, found 2 hours ago
CA $360
Roundtrip
found 2 hours ago
Select WestJet flight, departing Sun, Nov 30 from Pearson Intl. to Lynden Pindling Intl., returning Mon, Dec 1, priced at CA $360 found 2 hours ago
Tue, Feb 17 - Thu, Feb 19
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $366 Roundtrip, found 2 days ago
CA $366
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Tue, Feb 17 from Pearson Intl. to Lynden Pindling Intl., returning Thu, Feb 19, priced at CA $366 found 2 days ago
Fri, Dec 12 - Tue, Dec 16
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $367 Roundtrip, found 1 hour ago
CA $367
Roundtrip
found 1 hour ago
Select Air Transat flight, departing Fri, Dec 12 from Pearson Intl. to Lynden Pindling Intl., returning Tue, Dec 16, priced at CA $367 found 1 hour ago
Sun, Dec 7 - Fri, Dec 12
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $372 Roundtrip, found 10 hours ago
CA $372
Roundtrip
found 10 hours 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 10 hours ago
Sat, Jan 10 - Sat, Jan 17
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $403 Roundtrip, found 3 hours ago
CA $403
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Jan 10 from Pearson Intl. to Punta Cana Intl., returning Sat, Jan 17, priced at CA $403 found 3 hours ago
Thu, Dec 4 - Thu, Dec 25
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $408 Roundtrip, found 9 hours ago
CA $408
Roundtrip
found 9 hours ago
Select WestJet flight, departing Thu, Dec 4 from Pearson Intl. to Queen Beatrix Intl., returning Thu, Dec 25, priced at CA $408 found 9 hours ago
Tue, Dec 9 - Wed, Dec 24
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $413 Roundtrip, found 1 day ago
CA $413
Roundtrip
found 1 day ago
Select Air Canada flight, departing Tue, Dec 9 from Pearson Intl. to Queen Beatrix Intl., returning Wed, Dec 24, priced at CA $413 found 1 day ago
OriginDestinationTravel datesFlights from*
EWRSanto DomingoMarch 6 to March 15CA $351
EWRSanto DomingoMarch 6 to March 15CA $351
JFKOranjestadDecember 16 to December 23CA $423
EWRMontego BayJanuary 9 to January 9CA $431
JFKSanto DomingoDecember 12 to December 15CA $448
EWRSantiago de los CaballerosJanuary 27 to February 1CA $451
EWRSantiago de los CaballerosJanuary 27 to February 1CA $451
EWRNassauDecember 12 to December 16CA $508
JFKKingstonJanuary 31 to February 6CA $555
JFKKingstonJanuary 31 to February 6CA $555
LGAPiarcoJanuary 7 to January 20CA $595
BOSSantiago de los CaballerosDecember 14 to January 10CA $635
JFKPiarcoFebruary 5 to February 16CA $690
EWRPiarcoFebruary 6 to February 16CA $690
JFKSantiago de los CaballerosDecember 26 to December 30CA $1,004
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MIASan JuanNovember 29 to December 7CA $255
FLLSanto DomingoNovember 30 to December 3CA $295
FLLMontego BayNovember 29 to December 6CA $344
JFKSan JuanNovember 29 to November 30CA $386
JFKSan JuanNovember 29 to November 30CA $386
YYZMontego BayNovember 30 to December 1CA $460
EWRPunta CanaNovember 30 to December 4CA $460
EWRPunta CanaNovember 30 to December 4CA $460
JFKPunta CanaNovember 30 to December 4CA $478
YYZKingstonNovember 30 to December 14CA $518
JFKSanto DomingoNovember 29 to December 2CA $527
JFKSanto DomingoNovember 29 to December 2CA $527
YYZSan JuanNovember 29 to December 8CA $616
PHLSanto DomingoNovember 30 to December 4CA $668
BOSOranjestadNovember 30 to December 6CA $722
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Feb 13 - Feb 20

7 night stay

Toronto (YTO) to Montego Bay (MBJ)

WestJet • Roundtrip • Coach
Price was CA $4,178, price is now CA $1,626 per person
CA $1,626
per person
found 8 hours ago
Sunset at the Palms Resort - Adults Only - All Inclusive
4.5-star property

Sunset at the Palms Resort - Adults Only - All Inclusive

Jan 9 - Jan 16

7 night stay

Hamilton (YHM) to Montego Bay (MBJ)

Air Canada • Non-stop roundtrip • Coach
Price was CA $7,794, price is now CA $2,840 per person
CA $2,840
per person
found 1 day ago
Ocean Coral Spring - All Inclusive
5.0-star property

Ocean Coral Spring - All Inclusive

Jan 30 - Feb 6

7 night stay

Halifax (YHZ) to Montego Bay (MBJ)

Air Canada • Non-stop roundtrip • Coach
Price was CA $5,277, price is now CA $2,162 per person
CA $2,162
per person
found 1 day ago
Don't see what you're looking for?
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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 $255. 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 $255. 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 $255 and CA $1,004 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.