Flights To Caribbean - Cheap Flights Starting at CA $166

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 showing heritage elements and cuddly or friendly animals

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.

Sat, Sep. 20 - Sat, Sep. 27
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $267 Roundtrip, just found
CA $267
Roundtrip
just found
Select Flair Airlines flight, departing Sat, Sep. 20 from Pearson Intl. to Punta Cana Intl., returning Sat, Sep. 27, priced at CA $267 just found
Wed, Sep. 10 - Mon, Sep. 15
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $332 Roundtrip, just found
CA $332
Roundtrip
just found
Select Flair Airlines flight, departing Wed, Sep. 10 from Pearson Intl. to Norman Manley Intl., returning Mon, Sep. 15, priced at CA $332 just found
Mon, Oct. 27 - Thu, Oct. 30
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $348 Roundtrip, found 1 day ago
CA $348
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Oct. 27 from Pearson Intl. to Luis Munoz Marin Intl., returning Thu, Oct. 30, priced at CA $348 found 1 day ago
Sat, Mar. 7 - Sat, Mar. 14
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $351 Roundtrip, just found
CA $351
Roundtrip
just found
Select Arajet flight, departing Sat, Mar. 7 from Pearson Intl. to Punta Cana Intl., returning Sat, Mar. 14, priced at CA $351 just found
Wed, Aug. 6 - Mon, Aug. 11
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $424 Roundtrip, found 1 day ago
CA $424
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug. 6 from Pearson Intl. to Lynden Pindling Intl., returning Mon, Aug. 11, priced at CA $424 found 1 day ago
Sun, Oct. 26 - Sun, Nov. 2
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $424 Roundtrip, just found
CA $424
Roundtrip
just found
Select WestJet flight, departing Sun, Oct. 26 from Pearson Intl. to Queen Beatrix Intl., returning Sun, Nov. 2, priced at CA $424 just found
Fri, Nov. 21 - Sat, Nov. 29
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $430 Roundtrip, just found
CA $430
Roundtrip
just found
Select Air Transat flight, departing Fri, Nov. 21 from Pearson Intl. to Punta Cana Intl., returning Sat, Nov. 29, priced at CA $430 just found
Tue, Aug. 12 - Tue, Aug. 26
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $431 Roundtrip, found 5 hours ago
CA $431
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Tue, Aug. 12 from Pearson Intl. to Sir Donald Sangster Intl., returning Tue, Aug. 26, priced at CA $431 found 5 hours ago
OriginDestinationTravel datesFlights from*
MIASan JuanJuly 23 to July 31CA $241
MIASanto DomingoSeptember 2 to September 14CA $313
PHLSan JuanJuly 18 to July 22CA $383
EWRPunta CanaJuly 26 to August 2CA $415
PHLMontego BayJuly 29 to August 2CA $431
EWRNassauOctober 6 to October 12CA $438
FLLPiarcoSeptember 11 to September 18CA $510
EWRSantiago de los CaballerosAugust 15 to August 22CA $527
BOSSanto DomingoJuly 19 to August 2CA $527
LHRNassauSeptember 17 to September 24CA $1,067
LHRPunta CanaAugust 24 to September 9CA $1,255
LHRMontego BayAugust 5 to September 2CA $1,451
LHRSanto DomingoAugust 16 to August 24CA $1,563
LHRKingstonJuly 19 to July 31CA $1,574
BKKNassauSeptember 6 to September 9CA $2,543
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MIASan JuanJuly 13 to July 17CA $189
FLLSan JuanJuly 12 to July 16CA $238
BOSSan JuanJuly 11 to July 13CA $345
FLLOranjestadJuly 13 to July 17CA $384
EWRSanto DomingoJuly 12 to July 18CA $424
MIASanto DomingoJuly 12 to July 18CA $467
JFKSanto DomingoJuly 11 to July 17CA $530
YYZMontego BayJuly 12 to July 26CA $609
BOSSanto DomingoJuly 11 to July 18CA $614
EWRSantiago de los CaballerosJuly 11 to July 18CA $658
YYZKingstonJuly 13 to July 14CA $674
JFKMontego BayJuly 11 to July 14CA $684
MIAOranjestadJuly 12 to July 19CA $980
YYZPiarcoJuly 13 to July 27CA $1,037
YYZSantiago de los CaballerosJuly 12 to July 28CA $1,064
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Dorado Beach 5 Bedroom Villa
3.5-star property

Dorado Beach 5 Bedroom Villa

Aug 24 - Aug 29

5 night stay

Toronto (YYZ) to San Juan (SJU)

United • Non-stop • Coach

San Juan (SJU) to Toronto (YYZ)

Delta • Non-stop • Coach
per person
found 20 hours ago
Princess Grand Jamaica Resort - All Inclusive
4.5-star property

Princess Grand Jamaica Resort - All Inclusive

Sep 5 - Sep 12

7 night stay

Calgary (YYC) to Montego Bay (MBJ)

WestJet • Non-stop roundtrip • Coach
per person
found 1 day ago
Princess Senses The Mangrove Resort - Adults Only
4.0-star property

Princess Senses The Mangrove Resort - Adults Only

Sep 5 - Sep 12

7 night stay

Calgary (YYC) to Montego Bay (MBJ)

WestJet • Non-stop roundtrip • Coach
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
Stay at this 4.5-star 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! (1,003 reviews)
"Excellent location."

Reviewed on Jun. 28, 2025

Hotel El Convento
British Colonial - Nassau

British Colonial - Nassau

4 out of 5
Number One Bay St, Nassau
Stay at this 4-star 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 Aquaventure and Ocean Club Golf Course are located nearby.
8.6/10 Excellent! (1,719 reviews)
"Wonderful staff and beautiful resort style hotel. Amenities are excellent, including pools and restaurants. The only issue was the house keeping always ran later in the day. We would be out and about only to return late in the afternoon and the room still had not been cleaned. That being said, once ..."

Reviewed on Jul. 1, 2025

British 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
Stay at this 4-star 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! (1,006 reviews)
"The receptionist, Sarah, was incredibly helpful throughout my stay. She went above and beyond to accommodate all my needs and ensure I was comfortable. The location of the hotel is perfect, and everything was exceptionally clean. The rooftop pool and beautiful bar were the cherry on top, such amazing ..."

Reviewed on Jul. 2, 2025

Hotel 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
Stay at this 4.5-star 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 Ocean Club Golf Course are located nearby.
8.8/10 Excellent! (1,381 reviews)
"Perfect hotel for a family holiday."

Reviewed on Jun. 30, 2025

The 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 $189. 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 $189. 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 $189 and CA $2,543 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.