Flights To Caribbean - Cheap Flights Starting at CA $105

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Caribbean's top cities

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 16 - Fri, Jan 23
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 16 from Pearson Intl. to Punta Cana Intl., returning Fri, Jan 23, priced at CA $273 found 1 hour ago
Sat, Jan 17 - Sat, Jan 31
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $292 Roundtrip, found 19 hours ago
CA $292
Roundtrip
found 19 hours ago
Select Flair Airlines flight, departing Sat, Jan 17 from Pearson Intl. to Sir Donald Sangster Intl., returning Sat, Jan 31, priced at CA $292 found 19 hours ago
Tue, Apr 14 - Mon, Apr 20
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $329 Roundtrip, found 1 day ago
CA $329
Roundtrip
found 1 day ago
Select WestJet flight, departing Tue, Apr 14 from Pearson Intl. to Lynden Pindling Intl., returning Mon, Apr 20, priced at CA $329 found 1 day ago
Mon, Jan 12 - Fri, Jan 16
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $340 Roundtrip, found 4 days ago
CA $340
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Jan 12 from Pearson Intl. to Luis Munoz Marin Intl., returning Fri, Jan 16, priced at CA $340 found 4 days ago
Sun, Feb 8 - Sat, Feb 14
YUL
Pierre Elliott Trudeau Intl.
SJU
Luis Munoz Marin Intl.
CA $363 Roundtrip, found 1 day ago
CA $363
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Feb 8 from Pierre Elliott Trudeau Intl. to Luis Munoz Marin Intl., returning Sat, Feb 14, priced at CA $363 found 1 day ago
Tue, Mar 3 - Tue, Mar 10
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $366 Roundtrip, found 1 day ago
CA $366
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 3 from Pearson Intl. to Queen Beatrix Intl., returning Tue, Mar 10, priced at CA $366 found 1 day ago
Sat, Mar 28 - Mon, Mar 30
YUL
Pierre Elliott Trudeau Intl.
NAS
Lynden Pindling Intl.
CA $374 Roundtrip, found 1 day ago
CA $374
Roundtrip
found 1 day ago
Select WestJet flight, departing Sat, Mar 28 from Pierre Elliott Trudeau Intl. to Lynden Pindling Intl., returning Mon, Mar 30, priced at CA $374 found 1 day ago
Mon, Jan 12 - Sun, Jan 25
YUL
Pierre Elliott Trudeau Intl.
PUJ
Punta Cana Intl.
CA $402 Roundtrip, found 1 day ago
CA $402
Roundtrip
found 1 day ago
Select Arajet flight, departing Mon, Jan 12 from Pierre Elliott Trudeau Intl. to Punta Cana Intl., returning Sun, Jan 25, priced at CA $402 found 1 day ago
OriginDestinationTravel datesFlights from*
JFKNassauFebruary 27 to March 2CA $303
JFKNassauFebruary 27 to March 2CA $303
EWROranjestadJanuary 10 to January 17CA $312
EWRMontego BayFebruary 2 to February 6CA $379
EWRMontego BayFebruary 2 to February 6CA $379
EWRSanto DomingoFebruary 21 to February 25CA $381
JFKOranjestadJanuary 5 to January 11CA $414
JFKSanto DomingoJanuary 21 to February 4CA $425
JFKPiarcoJanuary 15 to January 22CA $438
JFKSantiago de los CaballerosFebruary 20 to March 3CA $475
EWRNassauJanuary 16 to January 19CA $503
JFKKingstonJanuary 24 to January 30CA $538
JFKKingstonJanuary 24 to January 30CA $538
JFKWest EndJanuary 8 to January 14CA $547
EWRKingstonFebruary 5 to February 9CA $565
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKSan JuanDecember 27 to December 29CA $460
FLLOranjestadDecember 28 to January 1CA $463
FLLNassauDecember 26 to December 31CA $532
JFKSantiago de los CaballerosDecember 27 to January 12CA $551
JFKSanto DomingoDecember 26 to January 1CA $752
JFKSanto DomingoDecember 26 to January 1CA $752
JFKPiarcoDecember 27 to February 3CA $764
BOSSanto DomingoDecember 26 to December 29CA $807
JFKMontego BayDecember 28 to January 1CA $923
JFKKingstonDecember 27 to December 31CA $930
JFKKingstonDecember 27 to December 31CA $930
BOSSantiago de los CaballerosDecember 27 to January 9CA $977
JFKOranjestadDecember 26 to December 26CA $1,262
JFKOranjestadDecember 26 to December 26CA $1,262
BOSOranjestadDecember 26 to January 5CA $1,604
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at Coolshade X
3.5-star property

Ocho Rios Villa at Coolshade X

Feb 2 - Feb 7

5 night stay

Toronto (YYZ) to Montego Bay (MBJ)

WestJet • Roundtrip • Coach
Price was CA $2,616, price is now CA $1,299 per person
CA $1,299
per person
found 8 hours ago
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Feb 21 - Feb 28

7 night stay

Edmonton (YEG) to Montego Bay (MBJ)

WestJet • Non-stop roundtrip • Coach
Price was CA $4,244, price is now CA $1,774 per person
CA $1,774
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 28 - Mar 7

7 night stay

Edmonton (YEG) to Santo Domingo (SDQ)

United • Non-stop roundtrip • Coach
Price was CA $3,463, price is now CA $1,474 per person
CA $1,474
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Toronto to Caribbean
View all trips

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 Junkanoo Beach and Ocean Club Golf Course 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! (1,376 reviews)
The hotel was very nice and modern, however it took awhile for service desk to answer the phone.

Reviewed on Dec 15, 2025

Opens in a new windowHotel Rumbao, a Tribute Portfolio Hotel
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 $273. 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 $273. 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 $273 and CA $1,604 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.