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.

Fri, Jan 9 - Tue, Feb 3
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $273 Roundtrip, found 1 hour ago
CA $273
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Fri, Jan 9 from Pearson Intl. to Punta Cana Intl., returning Tue, Feb 3, priced at CA $273 found 1 hour ago
Sat, Jan 31 - Thu, Feb 12
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $339 Roundtrip, found 20 hours ago
CA $339
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Sat, Jan 31 from Pearson Intl. to Luis Munoz Marin Intl., returning Thu, Feb 12, priced at CA $339 found 20 hours ago
Fri, Apr 10 - Sat, Apr 18
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $358 Roundtrip, just found
CA $358
Roundtrip
just found
Select Air Transat flight, departing Fri, Apr 10 from Pearson Intl. to Lynden Pindling Intl., returning Sat, Apr 18, priced at CA $358 just found
Tue, Jan 20 - Tue, Feb 3
YUL
Pierre Elliott Trudeau Intl.
SJU
Luis Munoz Marin Intl.
CA $403 Roundtrip, found 5 days ago
CA $403
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jan 20 from Pierre Elliott Trudeau Intl. to Luis Munoz Marin Intl., returning Tue, Feb 3, priced at CA $403 found 5 days ago
Tue, Feb 3 - Tue, Feb 17
YUL
Pierre Elliott Trudeau Intl.
AUA
Queen Beatrix Intl.
CA $411 Roundtrip, found 1 day ago
CA $411
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 3 from Pierre Elliott Trudeau Intl. to Queen Beatrix Intl., returning Tue, Feb 17, priced at CA $411 found 1 day ago
Wed, Jan 7 - Tue, Jan 27
YUL
Pierre Elliott Trudeau Intl.
PUJ
Punta Cana Intl.
CA $415 Roundtrip, just found
CA $415
Roundtrip
just found
Select Arajet flight, departing Wed, Jan 7 from Pierre Elliott Trudeau Intl. to Punta Cana Intl., returning Tue, Jan 27, priced at CA $415 just found
Wed, Jan 21 - Wed, Jan 28
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $417 Roundtrip, found 3 hours ago
CA $417
Roundtrip
found 3 hours ago
Select WestJet flight, departing Wed, Jan 21 from Pearson Intl. to Queen Beatrix Intl., returning Wed, Jan 28, priced at CA $417 found 3 hours ago
Sat, Jan 17 - Sat, Jan 24
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $421 Roundtrip, just found
CA $421
Roundtrip
just found
Select Flair Airlines flight, departing Sat, Jan 17 from Pearson Intl. to Sir Donald Sangster Intl., returning Sat, Jan 24, priced at CA $421 just found
Tue, Jan 6 - Tue, Jan 13
YHM
John C. Munro Hamilton Intl.
NAS
Lynden Pindling Intl.
CA $437 Roundtrip, found 4 days ago
CA $437
Roundtrip
found 4 days ago
Select Air Canada flight, departing Tue, Jan 6 from John C. Munro Hamilton Intl. to Lynden Pindling Intl., returning Tue, Jan 13, priced at CA $437 found 4 days ago
Sun, Jan 18 - Sat, Jan 24
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $444 Roundtrip, found 4 days ago
CA $444
Roundtrip
found 4 days ago
Select Flair Airlines flight, departing Sun, Jan 18 from Pearson Intl. to Norman Manley Intl., returning Sat, Jan 24, priced at CA $444 found 4 days ago
Wed, Dec 24 - Thu, Dec 25
YHM
John C. Munro Hamilton Intl.
PUJ
Punta Cana Intl.
CA $446 Roundtrip, found 1 day ago
CA $446
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Dec 24 from John C. Munro Hamilton Intl. to Punta Cana Intl., returning Thu, Dec 25, priced at CA $446 found 1 day ago
OriginDestinationTravel datesFlights from*
JFKSan JuanMarch 2 to March 10CA $272
EWRPunta CanaJanuary 29 to February 3CA $342
EWRSanto DomingoJanuary 28 to January 29CA $370
JFKSanto DomingoJanuary 24 to January 26CA $389
JFKPunta CanaJanuary 13 to January 21CA $403
EWRMontego BayJanuary 9 to January 15CA $434
LGASantiago de los CaballerosJanuary 25 to January 29CA $436
EWRSantiago de los CaballerosJanuary 28 to April 8CA $447
JFKSantiago de los CaballerosJanuary 28 to April 8CA $447
EWRNassauJanuary 6 to January 10CA $469
JFKPiarcoMarch 28 to April 5CA $481
JFKKingstonJanuary 26 to February 2CA $552
JFKKingstonJanuary 26 to February 2CA $552
EWRPiarcoJanuary 15 to January 19CA $616
EWRKingstonJanuary 15 to January 19CA $669
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKOranjestadDecember 20 to December 29CA $427
EWRSan JuanDecember 20 to December 27CA $731
EWRMontego BayDecember 21 to January 8CA $833
EWRSanto DomingoDecember 21 to December 31CA $868
EWRSanto DomingoDecember 21 to December 31CA $868
JFKSanto DomingoDecember 20 to January 13CA $871
JFKPiarcoDecember 19 to December 26CA $898
JFKPiarcoDecember 19 to December 26CA $898
JFKSantiago de los CaballerosDecember 21 to March 13CA $1,041
JFKSantiago de los CaballerosDecember 21 to March 13CA $1,041
JFKMontego BayDecember 19 to January 2CA $1,075
EWRPiarcoDecember 19 to December 26CA $1,159
EWRSantiago de los CaballerosDecember 20 to January 6CA $1,207
EWRKingstonDecember 19 to December 30CA $1,324
JFKKingstonDecember 21 to December 28CA $1,436
*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 15 - Jan 20

5 night stay

Toronto (YYZ) to Montego Bay (MBJ)

WestJet • Roundtrip • Coach
Price was CA $3,030, price is now CA $1,237 per person
CA $1,237
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 24 - Jan 30

6 night stay

Montreal (YUL) to Montego Bay (MBJ)

American Airlines • Non-stop roundtrip • Coach
Price was CA $6,613, price is now CA $2,433 per person
CA $2,433
per person
found 1 day ago
Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

Jan 29 - Feb 5

7 night stay

Montreal (YUL) to San Juan (SJU)

American Airlines • Non-stop roundtrip • Coach
Price was CA $3,549, price is now CA $1,419 per person
CA $1,419
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.
9/10 Wonderful! (1,005 reviews)
Hospitality to the best!!!

Reviewed on Dec 11, 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! (2,080 reviews)
I had an early morning meeting, so I picked up a sandwich and juice from the cafe, the night before and stored them in my refrigerator so I could meet my ride at 6:30 AM before breakfast was available. But the sandwich was fresh and tasty, and did the job. This hotel will definitely be my go-to place ...

Reviewed on Dec 10, 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! (1,360 reviews)
Great location for walking around old San Juan

Reviewed on Dec 9, 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! (1,427 reviews)
We stayed at the Reef at Atlantis for 5 days and 4 nights. Overall the grounds were immaculate, the rooms were spacious, staff were very friendly, and the decor was impressive. The downsides were that the waterpark was one of the main reasons we went, but every day only 3 of the slides were open. ...

Reviewed on Dec 10, 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 $272. 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 $272. 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 $272 and CA $1,436 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.