Flights To Caribbean - Cheap Flights Starting at CA $160

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, Oct 10 - Sun, Oct 11
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
CA $312 Roundtrip, found 1 day ago
CA $312
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 10 from John F. Kennedy Intl. to Luis Munoz Marin Intl., returning Sun, Oct 11, priced at CA $312 found 1 day ago
Wed, Oct 7 - Thu, Oct 15
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
CA $319 Roundtrip, found 1 day ago
CA $319
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 7 from John F. Kennedy Intl. to Luis Munoz Marin Intl., returning Thu, Oct 15, priced at CA $319 found 1 day ago
Tue, Sep 22 - Sun, Sep 27
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
CA $331 Roundtrip, found 1 day ago
CA $331
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 22 from John F. Kennedy Intl. to Luis Munoz Marin Intl., returning Sun, Sep 27, priced at CA $331 found 1 day ago
Fri, Sep 11 - Tue, Sep 15
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
CA $346 Roundtrip, found 7 hours ago
CA $346
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Fri, Sep 11 from John F. Kennedy Intl. to Luis Munoz Marin Intl., returning Tue, Sep 15, priced at CA $346 found 7 hours ago
Sat, Nov 14 - Sat, Nov 21
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $353 Roundtrip, found 6 hours ago
CA $353
Roundtrip
found 6 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 6 hours ago
Fri, Sep 11 - Sun, Sep 13
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $397 Roundtrip, just found
CA $397
Roundtrip
just found
Select WestJet flight, departing Fri, Sep 11 from Pearson Intl. to Lynden Pindling Intl., returning Sun, Sep 13, priced at CA $397 just found
Mon, Nov 2 - Wed, Nov 11
JFK
John F. Kennedy Intl.
MBJ
Sir Donald Sangster Intl.
CA $455 Roundtrip, found 6 hours ago
CA $455
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Mon, Nov 2 from John F. Kennedy Intl. to Sir Donald Sangster Intl., returning Wed, Nov 11, priced at CA $455 found 6 hours ago
Mon, Oct 26 - Wed, Oct 28
JFK
John F. Kennedy Intl.
PUJ
Punta Cana Intl.
CA $476 Roundtrip, found 1 day ago
CA $476
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Oct 26 from John F. Kennedy Intl. to Punta Cana Intl., returning Wed, Oct 28, priced at CA $476 found 1 day ago
Sun, Sep 6 - Tue, Sep 15
JFK
John F. Kennedy Intl.
SDQ
Las Americas Intl.
CA $484 Roundtrip, found 4 days ago
CA $484
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sun, Sep 6 from John F. Kennedy Intl. to Las Americas Intl., returning Tue, Sep 15, priced at CA $484 found 4 days ago
Wed, Sep 2 - Sun, Sep 6
JFK
John F. Kennedy Intl.
NAS
Lynden Pindling Intl.
CA $521 Roundtrip, found 4 days ago
CA $521
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Sep 2 from John F. Kennedy Intl. to Lynden Pindling Intl., returning Sun, Sep 6, priced at CA $521 found 4 days ago
OriginDestinationTravel datesFlights from*
JFKSan JuanOctober 10 to October 11CA $312
JFKMontego BayNovember 2 to November 11CA $455
JFKMontego BayNovember 2 to November 11CA $455
LGANassauOctober 15 to October 18CA $473
JFKPunta CanaOctober 26 to October 28CA $476
EWRNassauOctober 16 to October 18CA $480
JFKOranjestadOctober 19 to October 23CA $532
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
EWRKingstonOctober 5 to October 12CA $584
JFKPiarcoSeptember 18 to September 20CA $638
JFKPiarcoSeptember 18 to September 20CA $638
YYZSantiago de los CaballerosOctober 13 to October 20CA $855
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKSan JuanAugust 16 to August 27CA $523
JFKPiarcoAugust 16 to August 31CA $788
JFKOranjestadAugust 16 to August 25CA $805
JFKKingstonAugust 15 to September 1CA $821
EWRMontego BayAugust 14 to August 19CA $839
EWRMontego BayAugust 14 to August 19CA $839
JFKMontego BayAugust 14 to August 19CA $839
LGANassauAugust 15 to August 19CA $870
JFKPunta CanaAugust 14 to August 20CA $872
JFKPunta CanaAugust 14 to August 20CA $872
EWRPunta CanaAugust 15 to August 22CA $1,134
EWRSantiago de los CaballerosAugust 15 to August 18CA $1,175
EWRNassauAugust 16 to August 21CA $1,369
EWRKingstonAugust 15 to September 1CA $1,522
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 8 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.
8.6/10 Excellent! (2,880 reviews)
"The property itself was beautiful. A fantastic pool and a private beach! Staff were friendly but it often felt like service was quite slow (the hotel wasn’t all that busy, but when we let the front desk know that we didn’t have towels, it was almost an hour before we got any; similarly, it took us ..."

Reviewed on Aug 8, 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! (1,844 reviews)
"I called prior to our trip to speak with someone about our check in time ( flight landed 3am) and the concierge had already arranged for our off hours arrival ! I was so impressed with this! We found our room to be very clean, comfortable, and well appointed. We visited the coffee shop downstairs ..."

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 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 $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.