Flights To Caribbean - Cheap Flights Starting at CA $165

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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, May 23 - Tue, Jun 9
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $302 Roundtrip, found 20 hours ago
CA $302
Roundtrip
found 20 hours ago
Select Flair Airlines flight, departing Sat, May 23 from Pearson Intl. to Punta Cana Intl., returning Tue, Jun 9, priced at CA $302 found 20 hours ago
Mon, Mar 30 - Sun, Apr 12
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $386 Roundtrip, found 4 days ago
CA $386
Roundtrip
found 4 days ago
Select WestJet flight, departing Mon, Mar 30 from Pearson Intl. to Punta Cana Intl., returning Sun, Apr 12, priced at CA $386 found 4 days ago
Sun, May 17 - Sun, Jun 7
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $395 Roundtrip, found 4 hours ago
CA $395
Roundtrip
found 4 hours ago
Select WestJet flight, departing Sun, May 17 from Pearson Intl. to Sir Donald Sangster Intl., returning Sun, Jun 7, priced at CA $395 found 4 hours ago
Sat, Jun 13 - Tue, Jun 16
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $399 Roundtrip, found 19 hours ago
CA $399
Roundtrip
found 19 hours ago
Select Arajet flight, departing Sat, Jun 13 from Pearson Intl. to Punta Cana Intl., returning Tue, Jun 16, priced at CA $399 found 19 hours ago
Tue, May 19 - Wed, Jun 3
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $400 Roundtrip, found 6 days ago
CA $400
Roundtrip
found 6 days ago
Select WestJet flight, departing Tue, May 19 from Pearson Intl. to Queen Beatrix Intl., returning Wed, Jun 3, priced at CA $400 found 6 days ago
Sun, Apr 12 - Sat, Apr 18
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $403 Roundtrip, found 3 hours ago
CA $403
Roundtrip
found 3 hours ago
Select WestJet flight, departing Sun, Apr 12 from Pearson Intl. to Lynden Pindling Intl., returning Sat, Apr 18, priced at CA $403 found 3 hours ago
Mon, Apr 13 - Sun, Apr 19
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $403 Roundtrip, just found
CA $403
Roundtrip
just found
Select Porter Airlines flight, departing Mon, Apr 13 from Pearson Intl. to Lynden Pindling Intl., returning Sun, Apr 19, priced at CA $403 just found
Sat, Apr 25 - Tue, Apr 28
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $417 Roundtrip, found 16 hours ago
CA $417
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Sat, Apr 25 from Pearson Intl. to Luis Munoz Marin Intl., returning Tue, Apr 28, priced at CA $417 found 16 hours ago
OriginDestinationTravel datesFlights from*
EWRSanto DomingoMay 4 to May 13CA $427
JFKMontego BayJune 4 to August 17CA $446
JFKPiarcoMay 1 to May 5CA $468
JFKPiarcoMay 1 to May 5CA $468
LGANassauApril 18 to April 25CA $482
JFKOranjestadMay 3 to May 20CA $487
JFKNassauApril 18 to April 25CA $490
EWRNassauApril 12 to April 22CA $517
JFKSanto DomingoMay 16 to May 18CA $531
EWRKingstonJune 20 to July 4CA $588
JFKSantiago de los CaballerosApril 23 to May 4CA $593
JFKSantiago de los CaballerosApril 23 to May 4CA $593
EWRSantiago de los CaballerosMay 6 to May 27CA $635
JFKKingstonMay 2 to May 8CA $689
EWRPiarcoMay 15 to May 18CA $858
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MIANassauApril 4 to April 8CA $532
LGANassauApril 4 to April 7CA $545
FLLMontego BayApril 5 to April 11CA $554
JFKSan JuanApril 5 to April 9CA $585
JFKNassauApril 3 to April 5CA $673
JFKSantiago de los CaballerosApril 5 to April 16CA $689
JFKSantiago de los CaballerosApril 5 to April 16CA $689
EWRSantiago de los CaballerosApril 5 to April 9CA $699
EWRNassauApril 4 to April 7CA $724
EWROranjestadApril 5 to April 13CA $738
EWROranjestadApril 5 to April 13CA $738
EWRSanto DomingoApril 3 to April 6CA $745
EWRSanto DomingoApril 3 to April 6CA $745
JFKSanto DomingoApril 3 to April 6CA $745
JFKOranjestadApril 4 to April 10CA $867
*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

Jun 2 - Jun 7

5 night stay

Toronto (YTO) to Montego Bay (MBJ)

WestJet • Roundtrip • Coach
Price was CA $3,261, price is now CA $680 per person
CA $680
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

May 29 - Jun 5

7 night stay

Hamilton (YHM) to Montego Bay (MBJ)

Air Canada • Non-stop roundtrip • Coach
Price was CA $5,440, price is now CA $2,340 per person
CA $2,340
per person
found 1 day ago
Coral Costa Caribe Beach Resort - All Inclusive
4.0-star property

Coral Costa Caribe Beach Resort - All Inclusive

May 9 - May 16

7 night stay

Toronto (YTO) to Santo Domingo (SDQ)

Sterling Blue • Roundtrip • Coach
Price was CA $3,099, price is now CA $1,378 per person
CA $1,378
per person
found 1 day ago
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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)
My Hotel Convento stay was comfortable and pleasant. The hotel service was excellent and staff was very helpful and friendly.The old world charm makes this hotel in comparison to other hotels in the area a must experience by all who come to Old San Juan.

Reviewed on Mar 26, 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 Junkanoo Beach and Cable Beach are located nearby.
8.6/10 Excellent! (2,395 reviews)
Room location 444 was not ideal. It’s next to the elevator and you hear it moving up and down ALL night and early in the morning. Around 3:00am repairs were being done that cause a loud banging against metal sound. It last an hour. I had an early flight that morning so needless to say it was not ...

Reviewed on Mar 27, 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! (1,589 reviews)
Great location close to the cruise port

Reviewed on Mar 25, 2026

Opens in a new windowHotel Rumbao, a Tribute Portfolio Hotel
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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 Junkanoo Beach and Cable Beach are located nearby.
8.8/10 Excellent! (1,450 reviews)
Have a great time everything seems to add up though it’s very expensive in the end especially eating out

Reviewed on Mar 26, 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 $302. 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 16 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 May. 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 $302. 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 $302 and CA $867 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.