Flights To Caribbean - Cheap Flights Starting at CA $184

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

Punta Cana

Flights
Punta Cana

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.

Thu, Sep 17 - Sun, Sep 20
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $401 Roundtrip, found 1 day ago
CA $401
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Sep 17 from Pearson Intl. to Lynden Pindling Intl., returning Sun, Sep 20, priced at CA $401 found 1 day ago
Wed, Feb 3 - Sun, Feb 14
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $405 Roundtrip, found 2 days ago
CA $405
Roundtrip
found 2 days ago
Select Arajet flight, departing Wed, Feb 3 from Pearson Intl. to Luis Munoz Marin Intl., returning Sun, Feb 14, priced at CA $405 found 2 days ago
Wed, May 20 - Tue, Jun 16
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $424 Roundtrip, found 5 days ago
CA $424
Roundtrip
found 5 days ago
Select WestJet flight, departing Wed, May 20 from Pearson Intl. to Queen Beatrix Intl., returning Tue, Jun 16, priced at CA $424 found 5 days ago
Tue, Mar 2 - Wed, Mar 3
YUL
Pierre Elliott Trudeau Intl.
SJU
Luis Munoz Marin Intl.
CA $435 Roundtrip, found 8 hours ago
CA $435
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, Mar 2 from Pierre Elliott Trudeau Intl. to Luis Munoz Marin Intl., returning Wed, Mar 3, priced at CA $435 found 8 hours ago
Wed, Jul 29 - Wed, Aug 5
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $447 Roundtrip, found 2 hours ago
CA $447
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Jul 29 from Pearson Intl. to Luis Munoz Marin Intl., returning Wed, Aug 5, priced at CA $447 found 2 hours ago
Sat, Dec 5 - Wed, Dec 9
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $448 Roundtrip, found 1 hour ago
CA $448
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Sat, Dec 5 from Pearson Intl. to Punta Cana Intl., returning Wed, Dec 9, priced at CA $448 found 1 hour ago
Sun, Nov 15 - Sat, Nov 21
YUL
Pierre Elliott Trudeau Intl.
NAS
Lynden Pindling Intl.
CA $464 Roundtrip, found 1 day ago
CA $464
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sun, Nov 15 from Pierre Elliott Trudeau Intl. to Lynden Pindling Intl., returning Sat, Nov 21, priced at CA $464 found 1 day ago
Fri, Jan 29 - Fri, Feb 12
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $465 Roundtrip, found 6 days ago
CA $465
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Jan 29 from Pearson Intl. to Sir Donald Sangster Intl., returning Fri, Feb 12, priced at CA $465 found 6 days ago
Fri, Jan 8 - Tue, Jan 26
YUL
Pierre Elliott Trudeau Intl.
MBJ
Sir Donald Sangster Intl.
CA $466 Roundtrip, found 2 days ago
CA $466
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Jan 8 from Pierre Elliott Trudeau Intl. to Sir Donald Sangster Intl., returning Tue, Jan 26, priced at CA $466 found 2 days ago
Mon, Jun 15 - Mon, Jun 22
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $469 Roundtrip, found 1 hour ago
CA $469
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Mon, Jun 15 from Pearson Intl. to Norman Manley Intl., returning Mon, Jun 22, priced at CA $469 found 1 hour ago
Tue, Nov 3 - Tue, Nov 10
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $491 Roundtrip, found 4 hours ago
CA $491
Roundtrip
found 4 hours ago
Select Air Transat flight, departing Tue, Nov 3 from Pearson Intl. to Sir Donald Sangster Intl., returning Tue, Nov 10, priced at CA $491 found 4 hours ago
OriginDestinationTravel datesFlights from*
JFKSan JuanJune 1 to June 10CA $378
EWRSan JuanJune 13 to June 24CA $436
JFKMontego BayJuly 9 to July 14CA $442
JFKMontego BayJuly 9 to July 14CA $442
JFKPunta CanaJune 1 to June 5CA $460
JFKNassauJuly 19 to July 24CA $505
JFKNassauJuly 19 to July 24CA $505
EWRSanto DomingoJune 1 to June 10CA $527
EWRSanto DomingoJune 1 to June 10CA $527
JFKSanto DomingoJune 13 to June 20CA $552
JFKSantiago de los CaballerosJune 13 to July 11CA $569
JFKKingstonJune 3 to June 10CA $574
JFKKingstonJune 3 to June 10CA $574
JFKPiarcoJune 17 to June 30CA $606
EWRNassauJuly 19 to July 24CA $685
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKPiarcoMay 16 to June 30CA $545
JFKPiarcoMay 16 to June 30CA $545
JFKKingstonMay 15 to May 17CA $673
JFKKingstonMay 15 to May 17CA $673
JFKSantiago de los CaballerosMay 15 to May 21CA $771
JFKSantiago de los CaballerosMay 15 to May 21CA $771
JFKSan JuanMay 15 to May 18CA $776
JFKSan JuanMay 15 to May 18CA $776
JFKOranjestadMay 16 to May 17CA $811
JFKNassauMay 15 to May 18CA $820
JFKNassauMay 15 to May 18CA $820
EWRSan JuanMay 15 to May 19CA $894
LGAMontego BayMay 15 to May 20CA $1,011
EWRNassauMay 15 to May 18CA $1,325
JFKMontego BayMay 15 to May 18CA $1,394
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Silver Creek Resort
3.5-star property

Silver Creek Resort

Aug 2 - Aug 9

7 night stay

Toronto (YTO) to Montego Bay (MBJ)

WestJet • Roundtrip • Coach
Price was CA $4,536, price is now CA $981 per person
CA $981
per person
found 1 day ago
Coral Costa Caribe Beach Resort - All Inclusive
4.0-star property

Coral Costa Caribe Beach Resort - All Inclusive

Jun 18 - Jun 24

6 night stay

Hamilton (YHM) to Santo Domingo (SDQ)

Air Canada • Non-stop roundtrip • Coach
Price was CA $2,832, price is now CA $1,233 per person
CA $1,233
per person
found 12 hours ago
Sunset at the Palms Resort - Adults Only - All Inclusive
4.5-star property

Sunset at the Palms Resort - Adults Only - All Inclusive

Jun 21 - Jun 28

7 night stay

Toronto (YTO) to Montego Bay (MBJ)

Air Transat • Roundtrip • Coach
Price was CA $5,423, price is now CA $2,403 per person
CA $2,403
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 Condado Beach are located nearby.
9/10 Wonderful! (1,003 reviews)
We had an absolutely wonderful stay at this charming boutique, hotel centrally located in old San Juan, Puerto Rico. The open-air design gives it a unique airy feel, while the rooms are equipped with air-conditioning for comfort. I love the thoughtful touches each day – complementary water 24/7, ...

Reviewed on May 13, 2026

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 6 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Atlantis Casino and Cabbage Beach are located nearby.
8.6/10 Excellent! (2,565 reviews)
The hotel was wonderful from staff, cleaning crew, bartenders and maintenance team. Best stay ever!!!

Reviewed on May 13, 2026

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 Condado Beach are located nearby.
9/10 Wonderful! (1,676 reviews)
The staff was amazing. Especially Carlos at check-in and Nathaniel behind the bar! Room was clean and had everything we could have wanted. Loved it!

Reviewed on May 11, 2026

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 Cabbage Beach and Cable Beach are located nearby.
9/10 Wonderful! (1,469 reviews)
Great experience just a little pricey but a perfect get away

Reviewed on May 13, 2026

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 $378. 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 September. 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 $378. 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 $378 and CA $1,394 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.