Flights To Caribbean - Cheap Flights Starting at CA $186

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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 26 - Tue, Oct 6
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $252 Roundtrip, found 9 hours ago
CA $252
Roundtrip
found 9 hours ago
Select Arajet flight, departing Sat, Sep 26 from Pearson Intl. to Luis Munoz Marin Intl., returning Tue, Oct 6, priced at CA $252 found 9 hours ago
Sat, Oct 31 - Sat, Nov 7
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $361 Roundtrip, found 1 hour ago
CA $361
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Sat, Oct 31 from Pearson Intl. to Sir Donald Sangster Intl., returning Sat, Nov 7, priced at CA $361 found 1 hour ago
Sun, Oct 25 - Sat, Oct 31
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $419 Roundtrip, found 6 hours ago
CA $419
Roundtrip
found 6 hours ago
Select Air Canada flight, departing Sun, Oct 25 from Pearson Intl. to Lynden Pindling Intl., returning Sat, Oct 31, priced at CA $419 found 6 hours ago
Mon, Aug 24 - Sat, Aug 29
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $433 Roundtrip, found 1 day ago
CA $433
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Aug 24 from Pearson Intl. to Luis Munoz Marin Intl., returning Sat, Aug 29, priced at CA $433 found 1 day ago
Sun, Oct 25 - Sat, Oct 31
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $434 Roundtrip, found 6 hours ago
CA $434
Roundtrip
found 6 hours ago
Select WestJet flight, departing Sun, Oct 25 from Pearson Intl. to Lynden Pindling Intl., returning Sat, Oct 31, priced at CA $434 found 6 hours ago
Fri, Mar 5 - Tue, Mar 9
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $441 Roundtrip, found 5 days ago
CA $441
Roundtrip
found 5 days ago
Select Flair Airlines flight, departing Fri, Mar 5 from Pearson Intl. to Punta Cana Intl., returning Tue, Mar 9, priced at CA $441 found 5 days ago
Sat, Sep 26 - Thu, Oct 1
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $449 Roundtrip, found 2 days ago
CA $449
Roundtrip
found 2 days ago
Select Arajet flight, departing Sat, Sep 26 from Pearson Intl. to Norman Manley Intl., returning Thu, Oct 1, priced at CA $449 found 2 days ago
Wed, Sep 2 - Sat, Sep 12
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $452 Roundtrip, found 2 days ago
CA $452
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Wed, Sep 2 from Pearson Intl. to Lynden Pindling Intl., returning Sat, Sep 12, priced at CA $452 found 2 days ago
OriginDestinationTravel datesFlights from*
JFKSan JuanSeptember 7 to September 15CA $332
EWRSan JuanSeptember 19 to September 25CA $361
EWRSanto DomingoOctober 23 to November 1CA $427
JFKKingstonSeptember 30 to October 1CA $508
JFKKingstonSeptember 30 to October 1CA $508
EWRNassauOctober 20 to October 25CA $513
JFKMontego BaySeptember 15 to September 24CA $516
JFKMontego BaySeptember 15 to September 24CA $516
JFKPunta CanaSeptember 10 to September 17CA $544
LGAPiarcoAugust 7 to August 15CA $577
JFKPiarcoAugust 8 to August 12CA $625
EWRSantiago de los CaballerosOctober 21 to October 24CA $636
JFKSantiago de los CaballerosSeptember 23 to September 30CA $636
EWRKingstonAugust 20 to August 23CA $712
EWRPiarcoAugust 8 to August 12CA $1,209
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKSan JuanJuly 31 to August 13CA $654
JFKPiarcoAugust 1 to August 8CA $680
JFKKingstonAugust 2 to September 30CA $694
JFKKingstonAugust 2 to September 30CA $694
JFKMontego BayAugust 1 to October 25CA $806
JFKMontego BayAugust 1 to October 25CA $806
JFKSantiago de los CaballerosAugust 1 to September 5CA $845
JFKSantiago de los CaballerosAugust 1 to September 5CA $845
JFKNassauAugust 1 to August 5CA $878
JFKNassauAugust 1 to August 5CA $878
EWRSanto DomingoAugust 2 to August 11CA $933
JFKSanto DomingoJuly 31 to August 2CA $976
EWRNassauAugust 2 to August 7CA $1,001
EWRSantiago de los CaballerosAugust 2 to August 6CA $1,011
EWRMontego BayAugust 2 to August 5CA $1,388
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Isla Verde Beachfront Retreat With Parking
2.0-star property

Isla Verde Beachfront Retreat With Parking

Oct 16 - Oct 21

5 night stay

Toronto (YYZ) to San Juan (SJU)

Sterling Blue • Non-stop • Coach

San Juan (SJU) to Toronto (YYZ)

United • Non-stop • Coach
Price was CA $2,463, price is now CA $1,130 per person
CA $1,130
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 17 - Oct 24

7 night stay

Ottawa (YOW) to Montego Bay (MBJ)

United • Non-stop roundtrip • Coach
Price was CA $5,859, price is now CA $2,072 per person
CA $2,072
per person
found 1 day ago
Coral Costa Caribe Beach Resort - All Inclusive
4.0-star property

Coral Costa Caribe Beach Resort - All Inclusive

Oct 7 - Oct 14

7 night stay

Toronto (YYZ) to Santo Domingo (SDQ)

Sterling Blue • Coach

Santo Domingo (SDQ) to Toronto (YYZ)

American Airlines • Coach
Price was CA $3,013, price is now CA $1,303 per person
CA $1,303
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 Distrito T-Mobile are located nearby.
9.2/10 Wonderful! (1,006 reviews)
"Beautiful hotel in old san juan"

Reviewed on Jul 24, 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 Cable Beach and Junkanoo Beach are located nearby.
8.6/10 Excellent! (2,807 reviews)
"Love the stay"

Reviewed on Jul 23, 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 Distrito T-Mobile are located nearby.
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 Cable Beach and Aquaventure are located nearby.
9/10 Wonderful! (1,580 reviews)
"Great place but the food pricing is expensive. No luck on making food reservations. All booked 90 days ahead."

Reviewed on Jul 22, 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 $252. 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 $252. 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 $252 and CA $1,388 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.