Flights To Caribbean - Cheap Flights Starting at CA $152

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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 31 - Tue, Feb 3
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $283 Roundtrip, found 4 hours ago
CA $283
Roundtrip
found 4 hours ago
Select Flair Airlines flight, departing Sat, Jan 31 from Pearson Intl. to Punta Cana Intl., returning Tue, Feb 3, priced at CA $283 found 4 hours ago
Wed, Apr 1 - Sun, Apr 5
YUL
Pierre Elliott Trudeau Intl.
SJU
Luis Munoz Marin Intl.
CA $344 Roundtrip, found 3 days ago
CA $344
Roundtrip
found 3 days ago
Select Arajet flight, departing Wed, Apr 1 from Pierre Elliott Trudeau Intl. to Luis Munoz Marin Intl., returning Sun, Apr 5, priced at CA $344 found 3 days ago
Sun, Feb 8 - Wed, Feb 11
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $357 Roundtrip, found 11 hours ago
CA $357
Roundtrip
found 11 hours ago
Select Porter Airlines flight, departing Sun, Feb 8 from Pearson Intl. to Lynden Pindling Intl., returning Wed, Feb 11, priced at CA $357 found 11 hours ago
Wed, Jan 21 - Thu, Jan 29
YUL
Pierre Elliott Trudeau Intl.
PUJ
Punta Cana Intl.
CA $376 Roundtrip, found 3 days ago
CA $376
Roundtrip
found 3 days ago
Select Arajet flight, departing Wed, Jan 21 from Pierre Elliott Trudeau Intl. to Punta Cana Intl., returning Thu, Jan 29, priced at CA $376 found 3 days ago
Sat, May 2 - Sat, May 9
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 Sat, May 2 from Pearson Intl. to Luis Munoz Marin Intl., returning Sat, May 9, priced at CA $399 found 3 days ago
Mon, Jan 5 - Fri, Jan 16
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $409 Roundtrip, found 7 hours ago
CA $409
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Mon, Jan 5 from Pearson Intl. to Queen Beatrix Intl., returning Fri, Jan 16, priced at CA $409 found 7 hours ago
Tue, Feb 3 - Tue, Feb 10
YUL
Pierre Elliott Trudeau Intl.
AUA
Queen Beatrix Intl.
CA $413 Roundtrip, found 4 days ago
CA $413
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Feb 3 from Pierre Elliott Trudeau Intl. to Queen Beatrix Intl., returning Tue, Feb 10, priced at CA $413 found 4 days ago
Tue, Dec 16 - Thu, Dec 25
YUL
Pierre Elliott Trudeau Intl.
NAS
Lynden Pindling Intl.
CA $424 Roundtrip, found 1 hour ago
CA $424
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Tue, Dec 16 from Pierre Elliott Trudeau Intl. to Lynden Pindling Intl., returning Thu, Dec 25, priced at CA $424 found 1 hour ago
OriginDestinationTravel datesFlights from*
EWRSan JuanJanuary 27 to February 4CA $197
JFKSan JuanJanuary 26 to January 30CA $247
EWROranjestadJanuary 22 to January 29CA $329
EWRSanto DomingoFebruary 6 to February 13CA $363
EWRSanto DomingoFebruary 6 to February 13CA $363
EWRPiarcoJanuary 17 to February 8CA $389
JFKPiarcoJanuary 17 to February 8CA $389
JFKOranjestadJanuary 3 to January 9CA $420
EWRSantiago de los CaballerosFebruary 5 to February 8CA $434
EWRSantiago de los CaballerosFebruary 5 to February 8CA $434
JFKSanto DomingoJanuary 12 to February 1CA $446
JFKMontego BayFebruary 20 to March 6CA $453
EWRNassauJanuary 6 to January 10CA $469
EWRKingstonJanuary 22 to January 29CA $562
JFKKingstonDecember 23 to December 27CA $1,174
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
EWRSan JuanDecember 13 to December 17CA $350
JFKSan JuanDecember 12 to December 15CA $427
JFKPunta CanaDecember 14 to December 23CA $437
JFKPunta CanaDecember 14 to December 23CA $437
JFKOranjestadDecember 14 to December 26CA $454
JFKOranjestadDecember 14 to December 26CA $454
JFKMontego BayDecember 13 to December 27CA $573
JFKMontego BayDecember 13 to December 27CA $573
JFKSanto DomingoDecember 12 to December 16CA $624
JFKSanto DomingoDecember 12 to December 16CA $624
EWRSantiago de los CaballerosDecember 12 to December 15CA $654
EWRSantiago de los CaballerosDecember 12 to December 15CA $654
JFKSantiago de los CaballerosDecember 12 to December 15CA $699
JFKKingstonDecember 13 to December 17CA $835
JFKKingstonDecember 13 to December 17CA $835
*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

Jan 10 - Jan 17

7 night stay

Toronto (YYZ) to Montego Bay (MBJ)

Flair Airlines • Coach

Montego Bay (MBJ) to Toronto (YYZ)

United • Coach
Price was CA $4,037, price is now CA $1,583 per person
CA $1,583
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 25 - Jan 31

6 night stay

Edmonton (YEG) to Montego Bay (MBJ)

WestJet • Non-stop roundtrip • Coach
Price was CA $6,745, price is now CA $2,793 per person
CA $2,793
per person
found 1 day ago
Coral Costa Caribe Beach Resort - All Inclusive
4.0-star property

Coral Costa Caribe Beach Resort - All Inclusive

Feb 2 - Feb 9

7 night stay

Edmonton (YEG) to Santo Domingo (SDQ)

United • Non-stop • Coach

Santo Domingo (SDQ) to Edmonton (YEG)

WestJet • Non-stop • Coach
Price was CA $3,765, price is now CA $1,657 per person
CA $1,657
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.
9/10 Wonderful! (1,002 reviews)
Excellent

Reviewed on Dec 3, 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! (2,069 reviews)
The room was very clean and everyone was courteous at all times.

Reviewed on Dec 6, 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! (1,338 reviews)
The property is by the bay where all the cruise ships anchor but this is not a problem at all, they don't make noise, they are just gigantic. Hotel personnel was wonderful (except one morning our server was just OK) but overall a great place to stay, our room was fantastic and we will definitely, ...

Reviewed on Dec 3, 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! (1,428 reviews)
It’s beautiful and so much to do. Very expensive food and drinks and snacks. Great service

Reviewed on Dec 6, 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 $197. 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 $197. 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 $197 and CA $1,174 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.