Flights To Caribbean - Cheap Flights Starting at CA $170

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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.

Wed, Apr 22 - Sat, Apr 25
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $319 Roundtrip, found 6 days ago
CA $319
Roundtrip
found 6 days ago
Select Arajet flight, departing Wed, Apr 22 from Pearson Intl. to Punta Cana Intl., returning Sat, Apr 25, priced at CA $319 found 6 days ago
Fri, Jun 12 - Fri, Jun 19
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $372 Roundtrip, found 1 day ago
CA $372
Roundtrip
found 1 day ago
Select WestJet flight, departing Fri, Jun 12 from Pearson Intl. to Queen Beatrix Intl., returning Fri, Jun 19, priced at CA $372 found 1 day ago
Fri, Apr 10 - Thu, Apr 23
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $372 Roundtrip, just found
CA $372
Roundtrip
just found
Select American Airlines flight, departing Fri, Apr 10 from Pearson Intl. to Luis Munoz Marin Intl., returning Thu, Apr 23, priced at CA $372 just found
Tue, May 19 - Tue, May 26
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $377 Roundtrip, found 4 hours ago
CA $377
Roundtrip
found 4 hours ago
Select Flair Airlines flight, departing Tue, May 19 from Pearson Intl. to Punta Cana Intl., returning Tue, May 26, priced at CA $377 found 4 hours ago
Wed, Apr 15 - Mon, Apr 20
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $382 Roundtrip, found 2 days ago
CA $382
Roundtrip
found 2 days ago
Select United flight, departing Wed, Apr 15 from Pearson Intl. to Lynden Pindling Intl., returning Mon, Apr 20, priced at CA $382 found 2 days ago
Tue, Mar 31 - Thu, Apr 16
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $384 Roundtrip, found 1 day ago
CA $384
Roundtrip
found 1 day ago
Select WestJet flight, departing Tue, Mar 31 from Pearson Intl. to Sir Donald Sangster Intl., returning Thu, Apr 16, priced at CA $384 found 1 day ago
Tue, Apr 7 - Wed, Apr 15
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $389 Roundtrip, found 6 days ago
CA $389
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Tue, Apr 7 from Pearson Intl. to Lynden Pindling Intl., returning Wed, Apr 15, priced at CA $389 found 6 days ago
Tue, Jun 2 - Fri, Jun 5
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $416 Roundtrip, found 3 days ago
CA $416
Roundtrip
found 3 days ago
Select Air Canada flight, departing Tue, Jun 2 from Pearson Intl. to Lynden Pindling Intl., returning Fri, Jun 5, priced at CA $416 found 3 days ago
OriginDestinationTravel datesFlights from*
JFKSan JuanFebruary 23 to March 4CA $267
LGASanto DomingoFebruary 28 to March 7CA $334
EWRMontego BayMarch 4 to March 11CA $341
EWRMontego BayMarch 4 to March 11CA $341
EWRPunta CanaMarch 4 to March 11CA $344
EWRSanto DomingoFebruary 24 to February 26CA $355
JFKOranjestadApril 2 to April 6CA $396
JFKPunta CanaMarch 4 to March 11CA $438
JFKSantiago de los CaballerosMarch 6 to March 9CA $446
LGAKingstonFebruary 20 to February 26CA $451
EWRNassauMarch 4 to March 6CA $458
JFKNassauFebruary 26 to March 3CA $495
EWRKingstonFebruary 20 to February 26CA $496
JFKPiarcoMarch 14 to March 21CA $507
JFKKingstonMarch 3 to March 11CA $558
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKSan JuanFebruary 15 to February 19CA $567
EWRSanto DomingoFebruary 14 to February 18CA $661
EWRSanto DomingoFebruary 14 to February 18CA $661
JFKSanto DomingoFebruary 14 to February 18CA $690
JFKKingstonFebruary 15 to February 19CA $708
JFKKingstonFebruary 15 to February 19CA $708
EWRMontego BayFebruary 14 to February 18CA $746
JFKMontego BayFebruary 14 to February 18CA $817
EWRPunta CanaFebruary 13 to February 17CA $1,049
EWRPunta CanaFebruary 13 to February 17CA $1,049
JFKNassauFebruary 13 to February 18CA $1,066
JFKOranjestadFebruary 13 to February 16CA $1,110
JFKPunta CanaFebruary 13 to February 17CA $1,142
JFKPiarcoFebruary 13 to February 20CA $1,277
JFKPiarcoFebruary 13 to February 20CA $1,277
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at Coolshade X
3.5-star property

Ocho Rios Villa at Coolshade X

Apr 18 - Apr 25

7 night stay

Calgary (YYC) to Montego Bay (MBJ)

WestJet • Roundtrip • Coach
Price was CA $3,205, price is now CA $1,595 per person
CA $1,595
per person
found 1 day ago
HERITAGE RESIDENCES STYLE
3.0-star property

HERITAGE RESIDENCES STYLE

Apr 12 - Apr 18

6 night stay

Toronto (YYZ) to Santo Domingo (SDQ)

American Airlines • Non-stop roundtrip • Coach
Price was CA $5,186, price is now CA $2,624 per person
CA $2,624
per person
found 1 day ago
Ocho Rios Villa at the Palms VII
3.0-star property

Ocho Rios Villa at the Palms VII

Mar 24 - Mar 31

7 night stay

Toronto (YYZ) to Montego Bay (MBJ)

United • Non-stop roundtrip • Coach
Price was CA $3,693, price is now CA $1,886 per person
CA $1,886
per person
found 7 hours 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 Pan American Pier are located nearby.
9/10 Wonderful! (1,001 reviews)
Beautiful place in the middle of Old San Juan . Excellent location. The building and rooms are beautiful . Well maintained keeping the beautiful architecture and original old structures .

Reviewed on Feb 5, 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 8 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cable Beach and Pirates of Nassau Museum are located nearby.
8.6/10 Excellent! (2,241 reviews)
Very friendly staff, first class service, beautiful hotel.

Reviewed on Feb 5, 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 Pan American Pier are located nearby.
9/10 Wonderful! (1,500 reviews)
The front desk was amazing and explained everything, and every employee we came across was very pleasant and friendly! We had a great stay!!

Reviewed on Feb 1, 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 Cable Beach and Aquaventure are located nearby.
8.8/10 Excellent! (1,425 reviews)
Very nice clean rooms & friendly staff.

Reviewed on Feb 4, 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 $267. 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 April. 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 $267. 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 $267 and CA $1,277 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.