Flights To Caribbean - Cheap Flights Starting at CA $168

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

A marina with a white boat named 'Achina' docked, surrounded by palm trees and a building with a green roof.

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.

Sat, Sep 19 - Tue, Oct 6
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $247 Roundtrip, found 1 day ago
CA $247
Roundtrip
found 1 day ago
Select Arajet flight, departing Sat, Sep 19 from Pearson Intl. to Luis Munoz Marin Intl., returning Tue, Oct 6, priced at CA $247 found 1 day ago
Sat, Nov 14 - Sat, Nov 21
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $353 Roundtrip, found 7 hours ago
CA $353
Roundtrip
found 7 hours ago
Select Flair Airlines flight, departing Sat, Nov 14 from Pearson Intl. to Sir Donald Sangster Intl., returning Sat, Nov 21, priced at CA $353 found 7 hours ago
Sun, Sep 27 - Fri, Oct 2
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $397 Roundtrip, just found
CA $397
Roundtrip
just found
Select WestJet flight, departing Sun, Sep 27 from Pearson Intl. to Lynden Pindling Intl., returning Fri, Oct 2, priced at CA $397 just found
Fri, Nov 20 - Fri, Nov 27
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $401 Roundtrip, just found
CA $401
Roundtrip
just found
Select Air Transat flight, departing Fri, Nov 20 from Pearson Intl. to Lynden Pindling Intl., returning Fri, Nov 27, priced at CA $401 just found
Thu, Sep 10 - Thu, Sep 17
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $407 Roundtrip, just found
CA $407
Roundtrip
just found
Select Air Canada flight, departing Thu, Sep 10 from Pearson Intl. to Lynden Pindling Intl., returning Thu, Sep 17, priced at CA $407 just found
Sat, Dec 5 - Tue, Dec 15
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $415 Roundtrip, found 5 hours ago
CA $415
Roundtrip
found 5 hours ago
Select Flair Airlines flight, departing Sat, Dec 5 from Pearson Intl. to Punta Cana Intl., returning Tue, Dec 15, priced at CA $415 found 5 hours ago
Sat, Sep 19 - Tue, Oct 6
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $418 Roundtrip, found 1 day ago
CA $418
Roundtrip
found 1 day ago
Select United flight, departing Sat, Sep 19 from Pearson Intl. to Luis Munoz Marin Intl., returning Tue, Oct 6, priced at CA $418 found 1 day ago
Sat, Oct 24 - Sat, Oct 31
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $419 Roundtrip, found 2 hours ago
CA $419
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Sat, Oct 24 from Pearson Intl. to Lynden Pindling Intl., returning Sat, Oct 31, priced at CA $419 found 2 hours ago
OriginDestinationTravel datesFlights from*
JFKSan JuanOctober 10 to October 11CA $312
EWRSanto DomingoNovember 6 to November 13CA $442
EWRSanto DomingoNovember 6 to November 13CA $442
EWRPunta CanaOctober 20 to October 25CA $448
JFKPunta CanaOctober 26 to October 28CA $476
EWRNassauOctober 16 to October 18CA $480
JFKNassauSeptember 2 to September 6CA $521
JFKKingstonSeptember 15 to September 29CA $539
JFKKingstonSeptember 15 to September 29CA $539
EWROranjestadOctober 29 to November 3CA $550
JFKSantiago de los CaballerosOctober 27 to November 1CA $582
JFKSantiago de los CaballerosOctober 27 to November 1CA $582
EWRKingstonOctober 5 to October 12CA $584
EWRSantiago de los CaballerosSeptember 28 to October 7CA $602
JFKPiarcoSeptember 18 to September 20CA $638
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKSan JuanAugust 16 to August 27CA $523
JFKSan JuanAugust 16 to August 27CA $523
JFKSantiago de los CaballerosAugust 15 to August 26CA $666
JFKPiarcoAugust 16 to August 31CA $788
JFKOranjestadAugust 16 to August 25CA $805
JFKOranjestadAugust 16 to August 25CA $805
JFKKingstonAugust 14 to August 17CA $832
JFKKingstonAugust 14 to August 17CA $832
EWRMontego BayAugust 14 to August 19CA $839
EWRMontego BayAugust 14 to August 19CA $839
JFKMontego BayAugust 14 to August 19CA $839
JFKPunta CanaAugust 14 to August 20CA $872
EWRPunta CanaAugust 15 to August 22CA $1,134
EWROranjestadAugust 15 to August 22CA $1,208
JFKNassauAugust 15 to August 15CA $1,538
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Luca Hotel by Heritage Residences Signature Collection
3.5-star property

Luca Hotel by Heritage Residences Signature Collection

Oct 17 - Oct 23

6 night stay

Toronto (YYZ) to Santo Domingo (SDQ)

United • Non-stop roundtrip • Coach
Price was CA $6,075, price is now CA $1,142 per person
CA $1,142
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

Oct 5 - Oct 9

4 night stay

Montreal (YUL) to Montego Bay (MBJ)

United • Non-stop roundtrip • Coach
Price was CA $3,815, price is now CA $1,570 per person
CA $1,570
per person
found 1 day ago
Isla Verde Beachfront Retreat With Parking
2.0-star property

Isla Verde Beachfront Retreat With Parking

Oct 3 - Oct 10

7 night stay

Montreal (YUL) to San Juan (SJU)

United • Non-stop roundtrip • Coach
Price was CA $3,278, price is now CA $1,556 per person
CA $1,556
per person
found 10 hours 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.
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 Junkanoo Beach and Aquaventure are located nearby.
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! (1,845 reviews)
"Location!"

Reviewed on Aug 8, 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 Aquaventure and Atlantis Casino are located nearby.
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 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 $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 $1,538 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.