
Flights To Caribbean - Cheap Flights Starting at CA $147
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San Juan
Flights
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.
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $347 Roundtrip, just found
CA $347
Roundtrip
just found
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $349 Roundtrip, found 17 hours ago
CA $349
Roundtrip
found 17 hours ago
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $361 Roundtrip, just found
CA $361
Roundtrip
just found
YUL
Pierre Elliott Trudeau Intl.
SJU
Luis Munoz Marin Intl.
CA $381 Roundtrip, found 6 days ago
CA $381
Roundtrip
found 6 days ago
YUL
Pierre Elliott Trudeau Intl.
NAS
Lynden Pindling Intl.
CA $384 Roundtrip, found 6 days ago
CA $384
Roundtrip
found 6 days ago
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $388 Roundtrip, found 4 hours ago
CA $388
Roundtrip
found 4 hours ago
YUL
Pierre Elliott Trudeau Intl.
PUJ
Punta Cana Intl.
CA $402 Roundtrip, found 10 hours ago
CA $402
Roundtrip
found 10 hours ago
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $419 Roundtrip, found 2 hours ago
CA $419
Roundtrip
found 2 hours ago
Origin | Destination | Travel dates | Flights from* |
---|---|---|---|
JFK | Oranjestad | October 20 to October 27 | CA $389 |
EWR | Nassau | November 13 to November 18 | CA $422 |
EWR | Nassau | November 13 to November 18 | CA $422 |
JFK | Santo Domingo | October 21 to October 24 | CA $426 |
JFK | Nassau | October 18 to October 24 | CA $429 |
JFK | Santiago de los Caballeros | October 31 to November 3 | CA $439 |
JFK | Santiago de los Caballeros | October 31 to November 3 | CA $439 |
EWR | Oranjestad | October 15 to October 22 | CA $455 |
JFK | Piarco | January 6 to February 1 | CA $464 |
JFK | Piarco | January 6 to February 1 | CA $464 |
EWR | Santiago de los Caballeros | October 31 to November 3 | CA $470 |
BOS | Santiago de los Caballeros | November 27 to November 28 | CA $547 |
EWR | Kingston | October 15 to October 20 | CA $558 |
EWR | Piarco | December 28 to January 5 | CA $1,028 |
BOS | Piarco | December 17 to January 2 | CA $1,864 |
Origin | Destination | Travel dates | Flights from* |
---|---|---|---|
JFK | San Juan | October 3 to October 9 | CA $331 |
JFK | San Juan | October 3 to October 9 | CA $331 |
EWR | San Juan | October 4 to October 11 | CA $340 |
EWR | Santo Domingo | October 5 to October 8 | CA $475 |
EWR | Santo Domingo | October 5 to October 8 | CA $475 |
JFK | Punta Cana | October 5 to October 9 | CA $505 |
JFK | Punta Cana | October 5 to October 9 | CA $505 |
JFK | Santiago de los Caballeros | October 5 to October 9 | CA $507 |
JFK | Santiago de los Caballeros | October 5 to October 9 | CA $507 |
JFK | Santo Domingo | October 5 to October 8 | CA $528 |
EWR | Punta Cana | October 5 to October 9 | CA $532 |
LGA | Montego Bay | October 3 to October 6 | CA $606 |
JFK | Piarco | October 3 to October 14 | CA $616 |
JFK | Piarco | October 3 to October 14 | CA $616 |
BOS | Oranjestad | October 4 to October 9 | CA $690 |
Price found within the past 48 hours. Click for updated prices.



Travelers ❤️ These Caribbean 🏨

Hotel El Convento
100 Cristo St, San Juan
Stay at this 4.5-star 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! (1,013 reviews)
"Loved this hotel, the staff was amazing and really friendly. I also love the vibe that it gives. Pool wasn’t too big but perfect to just relax in!"
Reviewed on Sep 25, 2025

British Colonial - Nassau
Number One Bay St, Nassau
Stay at this 4-star 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 Junkanoo Beach and Cable Beach are located nearby.
8.6/10 Excellent! (1,971 reviews)
Worked for a nice overnight stay -last minute
"Due to incoming tropical storm our group of 8 was evacuated early from our catamaran in Abaco. We made it to Nassau and had to spend the night. The British Colonial had four rooms available for our group and we were pleased (it was off-season). The hotel is beautiful but if you don’t have an ocean ..."
Reviewed on Sep 26, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street, San Juan, Puerto Rico
Stay at this 4-star 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! (1,174 reviews)
"Me quede este año y el año pasado y me gusta mucho este hotel. El check in y el check out súper fácil y rápido. El area donde se encuentra el hotel es súper accesible porque te puedes ir a caminar en San Juan y encuentras de todo. Tiendas para hacer shopping, lugares para comer y por la noche hay ..."
Reviewed on Sep 24, 2025
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The Reef at Atlantis
Paradise Beach Drive, Paradise Island, New Providence
Stay at this 4.5-star 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! (1,426 reviews)
"The stay, property and food was delicious at Atlantis. The lack of free entertainment (shows, live music etc) was a big bummer for us. There was nothing to do night to relax. Way too much money was spent. $160 for a family of 4 to okay putt putt. The complimentary movies were not every night. There ..."
Reviewed on Sep 26, 2025
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.
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