Flights To Caribbean - Cheap Flights Starting at CA $155

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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.

Wed, Jan 21 - Tue, Jan 27
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $330 Roundtrip, found 1 hour ago
CA $330
Roundtrip
found 1 hour ago
Select Arajet flight, departing Wed, Jan 21 from Pearson Intl. to Punta Cana Intl., returning Tue, Jan 27, priced at CA $330 found 1 hour ago
Wed, May 6 - Sun, May 17
YUL
Pierre Elliott Trudeau Intl.
SJU
Luis Munoz Marin Intl.
CA $333 Roundtrip, found 1 hour ago
CA $333
Roundtrip
found 1 hour ago
Select Arajet flight, departing Wed, May 6 from Pierre Elliott Trudeau Intl. to Luis Munoz Marin Intl., returning Sun, May 17, priced at CA $333 found 1 hour ago
Sun, Jan 25 - Tue, Mar 24
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $366 Roundtrip, just found
CA $366
Roundtrip
just found
Select Porter Airlines flight, departing Sun, Jan 25 from Pearson Intl. to Lynden Pindling Intl., returning Tue, Mar 24, priced at CA $366 just found
Thu, Mar 26 - Mon, Mar 30
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $366 Roundtrip, just found
CA $366
Roundtrip
just found
Select WestJet flight, departing Thu, Mar 26 from Pearson Intl. to Lynden Pindling Intl., returning Mon, Mar 30, priced at CA $366 just found
Fri, Dec 12 - Sat, Dec 13
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $366 Roundtrip, found 2 hours ago
CA $366
Roundtrip
found 2 hours ago
Select Air Transat flight, departing Fri, Dec 12 from Pearson Intl. to Lynden Pindling Intl., returning Sat, Dec 13, priced at CA $366 found 2 hours ago
Sat, Dec 6 - Sat, Dec 13
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $369 Roundtrip, found 1 day ago
CA $369
Roundtrip
found 1 day 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 1 day ago
Mon, Feb 23 - Tue, Mar 3
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $399 Roundtrip, found 10 hours ago
CA $399
Roundtrip
found 10 hours ago
Select United flight, departing Mon, Feb 23 from Pearson Intl. to Lynden Pindling Intl., returning Tue, Mar 3, priced at CA $399 found 10 hours ago
Tue, Dec 9 - Wed, Dec 24
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $408 Roundtrip, found 1 day ago
CA $408
Roundtrip
found 1 day ago
Select WestJet flight, departing Tue, Dec 9 from Pearson Intl. to Queen Beatrix Intl., returning Wed, Dec 24, priced at CA $408 found 1 day ago
Thu, Mar 26 - Mon, Mar 30
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $417 Roundtrip, just found
CA $417
Roundtrip
just found
Select Air Canada flight, departing Thu, Mar 26 from Pearson Intl. to Lynden Pindling Intl., returning Mon, Mar 30, priced at CA $417 just found
OriginDestinationTravel datesFlights from*
JFKSan JuanFebruary 27 to February 27CA $239
EWRSan JuanFebruary 7 to February 13CA $255
EWRPunta CanaFebruary 24 to February 28CA $347
LGAMontego BayJanuary 8 to January 15CA $437
JFKSantiago de los CaballerosFebruary 1 to February 6CA $448
JFKNassauJanuary 23 to January 26CA $449
LGANassauJanuary 23 to January 26CA $449
EWRSantiago de los CaballerosJanuary 27 to February 1CA $450
EWRMontego BayJanuary 4 to January 7CA $457
JFKMontego BayMarch 5 to March 11CA $542
JFKKingstonFebruary 26 to March 5CA $550
LGAPiarcoJanuary 7 to January 20CA $595
JFKPiarcoMarch 12 to March 21CA $632
EWRPiarcoFebruary 6 to February 16CA $690
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
LGASanto DomingoDecember 6 to December 9CA $397
JFKSanto DomingoDecember 7 to December 11CA $448
JFKOranjestadDecember 5 to December 12CA $457
JFKOranjestadDecember 5 to December 12CA $457
JFKNassauDecember 7 to December 13CA $466
JFKNassauDecember 7 to December 13CA $466
JFKKingstonDecember 5 to January 17CA $552
EWRMontego BayDecember 7 to December 16CA $569
EWRPunta CanaDecember 5 to December 7CA $572
LGAPiarcoDecember 6 to December 16CA $584
JFKPunta CanaDecember 5 to December 7CA $602
EWRKingstonDecember 6 to January 15CA $696
EWRNassauDecember 5 to December 8CA $725
*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 1 - Feb 8

7 night stay

Montreal (YUL) to Montego Bay (MBJ)

United • Non-stop • Coach

Montego Bay (MBJ) to Montreal (YUL)

American Airlines • Non-stop • Coach
Price was CA $4,246, price is now CA $1,717 per person
CA $1,717
per person
found 19 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 22 - Jan 28

6 night stay

Montreal (YUL) to Montego Bay (MBJ)

Air Canada • Non-stop roundtrip • Coach
Price was CA $6,753, price is now CA $2,059 per person
CA $2,059
per person
found 1 day ago
Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

Feb 10 - Feb 17

7 night stay

Montreal (YUL) to San Juan (SJU)

United • Non-stop • Coach

San Juan (SJU) to Montreal (YUL)

American Airlines • Non-stop • Coach
Price was CA $4,423, price is now CA $1,810 per person
CA $1,810
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! (1,319 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! (1,434 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 $239. 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 16 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 $239. 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 $239 and CA $725 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.