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.

Tue, Oct 28 - Sun, Nov 2
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $347 Roundtrip, just found
CA $347
Roundtrip
just found
Select WestJet flight, departing Tue, Oct 28 from Pearson Intl. to Lynden Pindling Intl., returning Sun, Nov 2, priced at CA $347 just found
Sun, Nov 9 - Thu, Nov 13
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $349 Roundtrip, found 17 hours ago
CA $349
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sun, Nov 9 from Pearson Intl. to Luis Munoz Marin Intl., returning Thu, Nov 13, priced at CA $349 found 17 hours ago
Tue, Oct 28 - Thu, Oct 30
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $361 Roundtrip, just found
CA $361
Roundtrip
just found
Select WestJet flight, departing Tue, Oct 28 from Pearson Intl. to Punta Cana Intl., returning Thu, Oct 30, priced at CA $361 just found
Fri, Apr 17 - Sun, Apr 26
YUL
Pierre Elliott Trudeau Intl.
SJU
Luis Munoz Marin Intl.
CA $381 Roundtrip, found 6 days ago
CA $381
Roundtrip
found 6 days ago
Select Arajet flight, departing Fri, Apr 17 from Pierre Elliott Trudeau Intl. to Luis Munoz Marin Intl., returning Sun, Apr 26, priced at CA $381 found 6 days ago
Fri, Nov 14 - Mon, Nov 17
YUL
Pierre Elliott Trudeau Intl.
NAS
Lynden Pindling Intl.
CA $384 Roundtrip, found 6 days ago
CA $384
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Nov 14 from Pierre Elliott Trudeau Intl. to Lynden Pindling Intl., returning Mon, Nov 17, priced at CA $384 found 6 days ago
Mon, Nov 3 - Fri, Nov 7
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $388 Roundtrip, found 4 hours ago
CA $388
Roundtrip
found 4 hours ago
Select WestJet flight, departing Mon, Nov 3 from Pearson Intl. to Queen Beatrix Intl., returning Fri, Nov 7, priced at CA $388 found 4 hours ago
Tue, Oct 28 - Tue, Nov 4
YUL
Pierre Elliott Trudeau Intl.
PUJ
Punta Cana Intl.
CA $402 Roundtrip, found 10 hours ago
CA $402
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Oct 28 from Pierre Elliott Trudeau Intl. to Punta Cana Intl., returning Tue, Nov 4, priced at CA $402 found 10 hours ago
Thu, Oct 30 - Tue, Nov 4
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $419 Roundtrip, found 2 hours ago
CA $419
Roundtrip
found 2 hours ago
Select United flight, departing Thu, Oct 30 from Pearson Intl. to Sir Donald Sangster Intl., returning Tue, Nov 4, priced at CA $419 found 2 hours ago
OriginDestinationTravel datesFlights from*
JFKOranjestadOctober 20 to October 27CA $389
EWRNassauNovember 13 to November 18CA $422
EWRNassauNovember 13 to November 18CA $422
JFKSanto DomingoOctober 21 to October 24CA $426
JFKNassauOctober 18 to October 24CA $429
JFKSantiago de los CaballerosOctober 31 to November 3CA $439
JFKSantiago de los CaballerosOctober 31 to November 3CA $439
EWROranjestadOctober 15 to October 22CA $455
JFKPiarcoJanuary 6 to February 1CA $464
JFKPiarcoJanuary 6 to February 1CA $464
EWRSantiago de los CaballerosOctober 31 to November 3CA $470
BOSSantiago de los CaballerosNovember 27 to November 28CA $547
EWRKingstonOctober 15 to October 20CA $558
EWRPiarcoDecember 28 to January 5CA $1,028
BOSPiarcoDecember 17 to January 2CA $1,864
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKSan JuanOctober 3 to October 9CA $331
JFKSan JuanOctober 3 to October 9CA $331
EWRSan JuanOctober 4 to October 11CA $340
EWRSanto DomingoOctober 5 to October 8CA $475
EWRSanto DomingoOctober 5 to October 8CA $475
JFKPunta CanaOctober 5 to October 9CA $505
JFKPunta CanaOctober 5 to October 9CA $505
JFKSantiago de los CaballerosOctober 5 to October 9CA $507
JFKSantiago de los CaballerosOctober 5 to October 9CA $507
JFKSanto DomingoOctober 5 to October 8CA $528
EWRPunta CanaOctober 5 to October 9CA $532
LGAMontego BayOctober 3 to October 6CA $606
JFKPiarcoOctober 3 to October 14CA $616
JFKPiarcoOctober 3 to October 14CA $616
BOSOranjestadOctober 4 to October 9CA $690
*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

Oct 24 - Oct 31

7 night stay

Halifax (YHZ) to Santo Domingo (SDQ)

United • Non-stop roundtrip • Coach
Price was CA $2,942, price is now CA $1,192 per person
CA $1,192
per person
found 1 day ago
Dorado Beach 5 Bedroom Villa
3.5-star property

Dorado Beach 5 Bedroom Villa

Dec 13 - Dec 18

5 night stay

Toronto (YYZ) to San Juan (SJU)

American Airlines • Non-stop • Coach

San Juan (SJU) to Toronto (YYZ)

United • Non-stop • Coach
Price was CA $3,604, price is now CA $1,267 per person
CA $1,267
per person
found 12 hours ago
Ocho Rios Villa at The Palms
3.0-star property

Ocho Rios Villa at The Palms

Nov 10 - Nov 17

7 night stay

Toronto (YYZ) to Montego Bay (MBJ)

American Airlines • Non-stop • Coach

Montego Bay (MBJ) to Toronto (YYZ)

Air Canada • Non-stop • Coach
Price was CA $3,945, price is now CA $1,685 per person
CA $1,685
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
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

Opens in a new windowHotel El Convento
British Colonial - Nassau

British Colonial - Nassau

4 out of 5
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

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
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

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
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

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 $331. 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 October. 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 $331. 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 $331 and CA $1,864 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.