Flights To Caribbean - Cheap Flights Starting at CA $157

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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, Mar 20 - Tue, Apr 7
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $323 Roundtrip, found 12 hours ago
CA $323
Roundtrip
found 12 hours ago
Select Arajet flight, departing Fri, Mar 20 from Pearson Intl. to Punta Cana Intl., returning Tue, Apr 7, priced at CA $323 found 12 hours ago
Mon, Dec 8 - Wed, Dec 10
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $357 Roundtrip, found 1 day ago
CA $357
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Dec 8 from Pearson Intl. to Lynden Pindling Intl., returning Wed, Dec 10, priced at CA $357 found 1 day ago
Sat, Dec 13 - Sat, Dec 20
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $366 Roundtrip, just found
CA $366
Roundtrip
just found
Select Air Transat flight, departing Sat, Dec 13 from Pearson Intl. to Lynden Pindling Intl., returning Sat, Dec 20, priced at CA $366 just found
Wed, Jan 7 - Sat, Jan 10
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $366 Roundtrip, found 1 day ago
CA $366
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Wed, Jan 7 from Pearson Intl. to Lynden Pindling Intl., returning Sat, Jan 10, priced at CA $366 found 1 day ago
Sat, Dec 6 - Sat, Dec 13
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $369 Roundtrip, found 3 days ago
CA $369
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 6 from Pearson Intl. to Luis Munoz Marin Intl., returning Sat, Dec 13, priced at CA $369 found 3 days ago
Wed, Dec 10 - Wed, Dec 17
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $393 Roundtrip, found 3 hours ago
CA $393
Roundtrip
found 3 hours ago
Select Air Canada flight, departing Wed, Dec 10 from Pearson Intl. to Lynden Pindling Intl., returning Wed, Dec 17, priced at CA $393 found 3 hours ago
Mon, Feb 23 - Tue, Mar 3
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $399 Roundtrip, found 2 days ago
CA $399
Roundtrip
found 2 days ago
Select United flight, departing Mon, Feb 23 from Pearson Intl. to Lynden Pindling Intl., returning Tue, Mar 3, priced at CA $399 found 2 days ago
Tue, Dec 9 - Wed, Dec 24
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $408 Roundtrip, found 3 days ago
CA $408
Roundtrip
found 3 days ago
Select WestJet flight, departing Tue, Dec 9 from Pearson Intl. to Queen Beatrix Intl., returning Wed, Dec 24, priced at CA $408 found 3 days ago
OriginDestinationTravel datesFlights from*
JFKSan JuanFebruary 24 to March 4CA $247
EWRSanto DomingoMarch 1 to March 7CA $347
JFKPunta CanaJanuary 18 to January 25CA $413
JFKOranjestadJanuary 5 to January 13CA $421
JFKSantiago de los CaballerosJanuary 28 to February 3CA $448
EWRSantiago de los CaballerosJanuary 28 to February 3CA $448
EWRSantiago de los CaballerosJanuary 28 to February 3CA $448
JFKNassauJanuary 23 to January 26CA $449
JFKSanto DomingoJanuary 4 to January 27CA $456
EWRNassauJanuary 23 to January 26CA $460
JFKKingstonFebruary 26 to March 5CA $550
JFKKingstonFebruary 26 to March 5CA $550
JFKPiarcoJanuary 10 to January 31CA $579
JFKPiarcoJanuary 10 to January 31CA $579
EWRKingstonJanuary 3 to January 7CA $697
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKSan JuanDecember 6 to December 11CA $321
JFKSan JuanDecember 6 to December 11CA $321
EWRSanto DomingoDecember 6 to December 9CA $418
JFKSanto DomingoDecember 6 to December 8CA $558
EWRMontego BayDecember 7 to December 16CA $569
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
LGAKingstonDecember 6 to January 15CA $684
JFKPiarcoDecember 5 to February 27CA $692
JFKMontego BayDecember 5 to December 8CA $713
JFKNassauDecember 5 to December 8CA $717
EWRNassauDecember 5 to December 8CA $725
JFKKingstonDecember 6 to January 15CA $912
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

Feb 21 - Feb 28

7 night stay

Halifax (YHZ) to San Juan (SJU)

Air Canada • Non-stop roundtrip • Coach
Price was CA $3,057, price is now CA $1,173 per person
CA $1,173
per person
found 1 day ago
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Jan 3 - Jan 10

7 night stay

Toronto (YYZ) to Montego Bay (MBJ)

Flair Airlines • Roundtrip • Coach
Price was CA $4,675, price is now CA $1,715 per person
CA $1,715
per person
found 1 day ago
Ocho Rios Villa at The Palms
3.0-star property

Ocho Rios Villa at The Palms

Jan 18 - Jan 25

7 night stay

Toronto (YYZ) to Montego Bay (MBJ)

WestJet • Roundtrip • Coach
Price was CA $3,909, price is now CA $1,597 per person
CA $1,597
per person
found 21 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! (1,003 reviews)
Environment and location. Great Historic Hotel

Reviewed on Dec 1, 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! (2,057 reviews)
My room was spotless and front desk staff very pleasant. The only downside to this beautiful place is there’s very limited parking!

Reviewed on Dec 1, 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! (1,435 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 March. 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 $912 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.