Flights To Caribbean - Cheap Flights Starting at CA $146

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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.

Fri, Feb 20 - Tue, Feb 24
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $338 Roundtrip, found 2 days ago
CA $338
Roundtrip
found 2 days ago
Select Arajet flight, departing Fri, Feb 20 from Pearson Intl. to Punta Cana Intl., returning Tue, Feb 24, priced at CA $338 found 2 days ago
Wed, Nov 26 - Fri, Nov 28
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $350 Roundtrip, just found
CA $350
Roundtrip
just found
Select Air Transat flight, departing Wed, Nov 26 from Pearson Intl. to Lynden Pindling Intl., returning Fri, Nov 28, priced at CA $350 just found
Wed, Nov 26 - Wed, Nov 26
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $350 Roundtrip, found 9 hours ago
CA $350
Roundtrip
found 9 hours ago
Select Porter Airlines flight, departing Wed, Nov 26 from Pearson Intl. to Lynden Pindling Intl., returning Wed, Nov 26, priced at CA $350 found 9 hours ago
Wed, Nov 26 - Thu, Nov 27
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $350 Roundtrip, found 9 hours ago
CA $350
Roundtrip
found 9 hours ago
Select WestJet flight, departing Wed, Nov 26 from Pearson Intl. to Lynden Pindling Intl., returning Thu, Nov 27, priced at CA $350 found 9 hours ago
Sat, Feb 21 - Thu, Feb 26
YTZ
Billy Bishop Toronto City
NAS
Lynden Pindling Intl.
CA $359 Roundtrip, found 15 hours ago
CA $359
Roundtrip
found 15 hours ago
Select Porter Airlines flight, departing Sat, Feb 21 from Billy Bishop Toronto City to Lynden Pindling Intl., returning Thu, Feb 26, priced at CA $359 found 15 hours ago
Sat, Nov 29 - Sat, Dec 13
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $379 Roundtrip, found 6 days ago
CA $379
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Nov 29 from Pearson Intl. to Luis Munoz Marin Intl., returning Sat, Dec 13, priced at CA $379 found 6 days ago
Sat, Nov 29 - Thu, Dec 4
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $386 Roundtrip, found 14 hours ago
CA $386
Roundtrip
found 14 hours ago
Select United flight, departing Sat, Nov 29 from Pearson Intl. to Lynden Pindling Intl., returning Thu, Dec 4, priced at CA $386 found 14 hours ago
Wed, Dec 3 - Thu, Dec 25
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $412 Roundtrip, found 5 hours ago
CA $412
Roundtrip
found 5 hours ago
Select WestJet flight, departing Wed, Dec 3 from Pearson Intl. to Queen Beatrix Intl., returning Thu, Dec 25, priced at CA $412 found 5 hours ago
Mon, Feb 23 - Tue, Feb 24
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $417 Roundtrip, found 3 hours ago
CA $417
Roundtrip
found 3 hours ago
Select Flair Airlines flight, departing Mon, Feb 23 from Pearson Intl. to Punta Cana Intl., returning Tue, Feb 24, priced at CA $417 found 3 hours ago
OriginDestinationTravel datesFlights from*
LGASan JuanDecember 8 to December 12CA $213
EWRSan JuanFebruary 22 to February 26CA $247
EWRPunta CanaDecember 8 to December 12CA $339
JFKPunta CanaJanuary 5 to January 16CA $397
EWRMontego BayDecember 11 to January 15CA $415
EWRMontego BayDecember 11 to January 15CA $415
JFKOranjestadDecember 9 to January 15CA $423
JFKSanto DomingoDecember 12 to December 15CA $448
LGANassauJanuary 28 to February 3CA $449
JFKNassauMarch 6 to March 14CA $450
LGASantiago de los CaballerosDecember 30 to January 28CA $463
EWRNassauJanuary 9 to January 12CA $471
JFKSantiago de los CaballerosDecember 31 to January 30CA $537
JFKKingstonJanuary 12 to January 20CA $561
JFKPiarcoFebruary 20 to March 1CA $785
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
FLLSan JuanNovember 28 to December 4CA $303
JFKSan JuanNovember 29 to November 30CA $386
JFKSan JuanNovember 29 to November 30CA $386
YYZPunta CanaNovember 29 to December 2CA $425
YYZKingstonNovember 30 to December 23CA $503
YYZOranjestadNovember 30 to December 4CA $533
EWRSan JuanNovember 28 to December 2CA $542
JFKSanto DomingoNovember 29 to December 2CA $572
JFKSanto DomingoNovember 29 to December 2CA $572
EWRSanto DomingoNovember 28 to December 2CA $606
YYZPiarcoNovember 28 to December 5CA $639
BOSOranjestadNovember 28 to December 3CA $681
JFKMontego BayNovember 28 to December 1CA $729
JFKMontego BayNovember 28 to December 1CA $729
MIAPunta CanaNovember 28 to December 1CA $883
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
The Oliver Hotel
3.0-star property

The Oliver Hotel

Feb 8 - Feb 15

7 night stay

Toronto (YTO) to San Juan (SJU)

United • Non-stop roundtrip • Coach
Price was CA $2,663, price is now CA $1,062 per person
CA $1,062
per person
found 1 day ago
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Feb 15 - Feb 22

7 night stay

Toronto (YTO) to Montego Bay (MBJ)

Air Canada • Non-stop roundtrip • Coach
Price was CA $4,188, price is now CA $1,636 per person
CA $1,636
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

Feb 5 - Feb 10

5 night stay

Toronto (YTO) to Montego Bay (MBJ)

Flair Airlines • Coach

Montego Bay (MBJ) to Toronto (YTO)

WestJet • Coach
Price was CA $5,671, price is now CA $2,226 per person
CA $2,226
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! (1,296 reviews)
Room was great. Pool was extremely small and pretty disgusting, dirty, no towels and even all the seats were gross. Definitely a bummer.

Reviewed on Nov 19, 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.