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, Jan 30 - Tue, Feb 24
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $323 Roundtrip, found 1 day ago
CA $323
Roundtrip
found 1 day ago
Select Flair Airlines flight, departing Fri, Jan 30 from Pearson Intl. to Punta Cana Intl., returning Tue, Feb 24, priced at CA $323 found 1 day ago
Wed, Apr 22 - Sun, Apr 26
YUL
Pierre Elliott Trudeau Intl.
SJU
Luis Munoz Marin Intl.
CA $337 Roundtrip, found 7 hours ago
CA $337
Roundtrip
found 7 hours ago
Select Arajet flight, departing Wed, Apr 22 from Pierre Elliott Trudeau Intl. to Luis Munoz Marin Intl., returning Sun, Apr 26, priced at CA $337 found 7 hours ago
Wed, Nov 26 - Sun, Nov 30
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $348 Roundtrip, found 1 hour ago
CA $348
Roundtrip
found 1 hour ago
Select Air Transat flight, departing Wed, Nov 26 from Pearson Intl. to Lynden Pindling Intl., returning Sun, Nov 30, priced at CA $348 found 1 hour ago
Tue, Dec 9 - Sat, Dec 13
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $349 Roundtrip, found 1 day ago
CA $349
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Dec 9 from Pearson Intl. to Luis Munoz Marin Intl., returning Sat, Dec 13, priced at CA $349 found 1 day ago
Fri, Dec 5 - Wed, Dec 17
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $394 Roundtrip, found 17 hours ago
CA $394
Roundtrip
found 17 hours ago
Select United flight, departing Fri, Dec 5 from Pearson Intl. to Queen Beatrix Intl., returning Wed, Dec 17, priced at CA $394 found 17 hours ago
Fri, Apr 24 - Thu, May 7
YUL
Pierre Elliott Trudeau Intl.
PUJ
Punta Cana Intl.
CA $403 Roundtrip, found 16 hours ago
CA $403
Roundtrip
found 16 hours ago
Select Arajet flight, departing Fri, Apr 24 from Pierre Elliott Trudeau Intl. to Punta Cana Intl., returning Thu, May 7, priced at CA $403 found 16 hours ago
Sat, Jan 17 - Sat, Jan 24
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $404 Roundtrip, found 1 hour ago
CA $404
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Sat, Jan 17 from Pearson Intl. to Sir Donald Sangster Intl., returning Sat, Jan 24, priced at CA $404 found 1 hour ago
Sat, Mar 7 - Thu, Mar 12
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $432 Roundtrip, found 2 days ago
CA $432
Roundtrip
found 2 days ago
Select Flair Airlines flight, departing Sat, Mar 7 from Pearson Intl. to Norman Manley Intl., returning Thu, Mar 12, priced at CA $432 found 2 days ago
OriginDestinationTravel datesFlights from*
EWRSanto DomingoJanuary 19 to January 23CA $388
EWRPunta CanaJanuary 24 to January 27CA $389
EWROranjestadDecember 6 to December 13CA $406
EWRMontego BayDecember 7 to December 16CA $413
JFKPiarcoJanuary 23 to January 26CA $417
JFKOranjestadDecember 15 to December 24CA $428
EWRSantiago de los CaballerosDecember 13 to December 20CA $437
JFKSanto DomingoDecember 4 to December 11CA $448
JFKMontego BayDecember 7 to December 16CA $454
JFKNassauDecember 14 to December 30CA $489
EWRNassauNovember 28 to December 2CA $511
LGAKingstonDecember 2 to December 9CA $518
EWRKingstonDecember 12 to December 16CA $547
JFKKingstonDecember 3 to December 9CA $574
EWRPiarcoJanuary 15 to January 24CA $625
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
FLLSan JuanNovember 21 to November 24CA $217
EWRPunta CanaNovember 23 to November 27CA $405
EWRPunta CanaNovember 23 to November 27CA $405
EWRSan JuanNovember 22 to November 29CA $410
LGAKingstonNovember 23 to November 27CA $465
JFKMontego BayNovember 22 to November 26CA $509
JFKMontego BayNovember 22 to November 26CA $509
BOSOranjestadNovember 23 to November 27CA $515
LGANassauNovember 22 to November 26CA $520
BOSNassauNovember 21 to November 24CA $529
EWRNassauNovember 22 to November 26CA $529
EWRKingstonNovember 23 to November 27CA $542
YYZOranjestadNovember 22 to November 27CA $608
BOSPunta CanaNovember 22 to November 29CA $1,114
BOSKingstonNovember 23 to November 29CA $1,138
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Lazy Parrot Inn
3.0-star property

Lazy Parrot Inn

Feb 1 - Feb 8

7 night stay

Toronto (YYZ) to San Juan (SJU)

United • Non-stop roundtrip • Coach
Price was CA $1,705, price is now CA $772 per person
CA $772
per person
found 1 day ago
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Jan 6 - Jan 12

6 night stay

Ottawa (YOW) to Montego Bay (MBJ)

WestJet • Non-stop • Coach

Montego Bay (MBJ) to Ottawa (YOW)

United • Non-stop • Coach
Price was CA $3,628, price is now CA $1,466 per person
CA $1,466
per person
found 11 hours ago
Ocho Rios Villa at The Palms
3.0-star property

Ocho Rios Villa at The Palms

Feb 1 - Feb 8

7 night stay

Toronto (YYZ) to Montego Bay (MBJ)

Flair Airlines • Roundtrip • Coach
Price was CA $3,956, price is now CA $1,663 per person
CA $1,663
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! (1,001 reviews)
Beautiful hotel right in the heart of old San Juan!

Reviewed on Nov 12, 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! (2,027 reviews)
I really like the calmness they have there sweet place to relax

Reviewed on Nov 11, 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! (1,263 reviews)
The Marriot property has been significantly updated …. Quite an improvement!

Reviewed on Nov 9, 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! (1,427 reviews)
We had a wonderful time! It’s our second time going to the Atlantis reef. We loved everything about it the food, the staff. We highly recommend!

Reviewed on Nov 10, 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 $217. 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 January. 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 $217. 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 $217 and CA $1,138 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.