Flights To Caribbean - Cheap Flights Starting at CA $147

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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.

Thu, Jan 29 - Thu, Feb 5
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $337 Roundtrip, found 15 hours ago
CA $337
Roundtrip
found 15 hours ago
Select Flair Airlines flight, departing Thu, Jan 29 from Pearson Intl. to Punta Cana Intl., returning Thu, Feb 5, priced at CA $337 found 15 hours ago
Fri, May 22 - Thu, May 28
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $338 Roundtrip, just found
CA $338
Roundtrip
just found
Select Arajet flight, departing Fri, May 22 from Pearson Intl. to Punta Cana Intl., returning Thu, May 28, priced at CA $338 just found
Wed, Nov 26 - Wed, Dec 3
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $348 Roundtrip, found 2 days ago
CA $348
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Wed, Nov 26 from Pearson Intl. to Lynden Pindling Intl., returning Wed, Dec 3, priced at CA $348 found 2 days ago
Wed, Nov 26 - Fri, Dec 5
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $348 Roundtrip, found 2 days ago
CA $348
Roundtrip
found 2 days ago
Select Air Transat flight, departing Wed, Nov 26 from Pearson Intl. to Lynden Pindling Intl., returning Fri, Dec 5, priced at CA $348 found 2 days ago
Sun, Nov 23 - Thu, Nov 27
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $349 Roundtrip, just found
CA $349
Roundtrip
just found
Select WestJet flight, departing Sun, Nov 23 from Pearson Intl. to Lynden Pindling Intl., returning Thu, Nov 27, priced at CA $349 just found
Mon, Nov 24 - Wed, Dec 17
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $369 Roundtrip, found 3 days ago
CA $369
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Nov 24 from Pearson Intl. to Luis Munoz Marin Intl., returning Wed, Dec 17, priced at CA $369 found 3 days ago
Tue, Feb 24 - Sat, Mar 7
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $384 Roundtrip, found 5 days ago
CA $384
Roundtrip
found 5 days ago
Select United flight, departing Tue, Feb 24 from Pearson Intl. to Luis Munoz Marin Intl., returning Sat, Mar 7, priced at CA $384 found 5 days ago
Tue, Feb 3 - Wed, Feb 11
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $408 Roundtrip, found 4 hours ago
CA $408
Roundtrip
found 4 hours ago
Select United flight, departing Tue, Feb 3 from Pearson Intl. to Queen Beatrix Intl., returning Wed, Feb 11, priced at CA $408 found 4 hours ago
OriginDestinationTravel datesFlights from*
EWRSan JuanFebruary 22 to February 26CA $247
EWROranjestadDecember 9 to December 16CA $307
EWRMontego BayDecember 9 to January 15CA $388
JFKPunta CanaFebruary 2 to February 6CA $397
JFKPunta CanaFebruary 2 to February 6CA $397
EWRSanto DomingoJanuary 19 to January 22CA $427
JFKOranjestadFebruary 2 to March 2CA $446
JFKSanto DomingoDecember 12 to December 19CA $447
JFKSantiago de los CaballerosJanuary 23 to February 6CA $447
LGANassauJanuary 28 to February 3CA $449
JFKPiarcoDecember 9 to December 28CA $451
JFKPiarcoDecember 9 to December 28CA $451
JFKMontego BayDecember 5 to December 11CA $453
JFKNassauDecember 6 to December 10CA $463
JFKKingstonJanuary 12 to January 20CA $561
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MIASanto DomingoNovember 29 to December 10CA $340
EWRSan JuanNovember 30 to December 4CA $427
EWRSan JuanNovember 30 to December 4CA $427
BOSNassauNovember 29 to December 6CA $427
JFKOranjestadNovember 30 to December 4CA $435
JFKOranjestadNovember 30 to December 4CA $435
BOSPunta CanaNovember 30 to December 4CA $454
JFKSan JuanNovember 30 to December 4CA $461
MIANassauNovember 30 to December 4CA $485
EWRSantiago de los CaballerosNovember 30 to December 4CA $682
EWRSantiago de los CaballerosNovember 30 to December 4CA $682
JFKMontego BayNovember 28 to December 1CA $729
JFKMontego BayNovember 28 to December 1CA $729
LGAKingstonNovember 29 to December 2CA $760
JFKKingstonNovember 30 to December 6CA $778
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Coral Costa Caribe Beach Resort - All Inclusive
4.0-star property

Coral Costa Caribe Beach Resort - All Inclusive

Dec 8 - Dec 14

6 night stay

Toronto (YTO) to Santo Domingo (SDQ)

Air Transat • Roundtrip • Coach
Price was CA $2,638, price is now CA $1,005 per person
CA $1,005
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

Jan 13 - Jan 19

6 night stay

Toronto (YTO) to Montego Bay (MBJ)

WestJet • Roundtrip • Coach
Price was CA $6,604, price is now CA $2,476 per person
CA $2,476
per person
found 1 day ago
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Jan 14 - Jan 21

7 night stay

Toronto (YYZ) to Montego Bay (MBJ)

WestJet • Roundtrip • Coach
Price was CA $3,939, price is now CA $1,617 per person
CA $1,617
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 Pan American Pier are located nearby.
8.8/10 Excellent! (1,000 reviews)
The room was very clean staff was very friendly enjoyed my stay and will go back again 😊

Reviewed on Nov 15, 2025

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! (2,039 reviews)
This property was lovely and the staff were incredibly nice and helpful.

Reviewed on Nov 18, 2025

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! (1,279 reviews)
Service, early checkin great!

Reviewed on Nov 15, 2025

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! (1,431 reviews)
Overall friendliness of the staff

Reviewed on Nov 18, 2025

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.

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.