Flights To Caribbean - Cheap Flights Starting at CA $157

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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.

Sat, Sep. 6 - Sat, Sep. 13
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $267 Roundtrip, just found
CA $267
Roundtrip
just found
Select Flair Airlines flight, departing Sat, Sep. 6 from Pearson Intl. to Punta Cana Intl., returning Sat, Sep. 13, priced at CA $267 just found
Tue, Oct. 28 - Tue, Nov. 4
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $348 Roundtrip, found 5 days ago
CA $348
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Oct. 28 from Pearson Intl. to Luis Munoz Marin Intl., returning Tue, Nov. 4, priced at CA $348 found 5 days ago
Wed, Sep. 17 - Sat, Sep. 27
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $355 Roundtrip, found 14 hours ago
CA $355
Roundtrip
found 14 hours ago
Select Arajet flight, departing Wed, Sep. 17 from Pearson Intl. to Punta Cana Intl., returning Sat, Sep. 27, priced at CA $355 found 14 hours ago
Mon, Oct. 6 - Fri, Oct. 10
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $377 Roundtrip, found 4 hours ago
CA $377
Roundtrip
found 4 hours ago
Select Flair Airlines flight, departing Mon, Oct. 6 from Pearson Intl. to Norman Manley Intl., returning Fri, Oct. 10, priced at CA $377 found 4 hours ago
Sat, Sep. 6 - Sat, Sep. 13
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $380 Roundtrip, just found
CA $380
Roundtrip
just found
Select WestJet flight, departing Sat, Sep. 6 from Pearson Intl. to Punta Cana Intl., returning Sat, Sep. 13, priced at CA $380 just found
Sun, Oct. 5 - Thu, Oct. 16
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $383 Roundtrip, found 5 days ago
CA $383
Roundtrip
found 5 days ago
Select United flight, departing Sun, Oct. 5 from Pearson Intl. to Luis Munoz Marin Intl., returning Thu, Oct. 16, priced at CA $383 found 5 days ago
Thu, Aug. 14 - Mon, Aug. 18
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $397 Roundtrip, found 4 days ago
CA $397
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Aug. 14 from Pearson Intl. to Lynden Pindling Intl., returning Mon, Aug. 18, priced at CA $397 found 4 days ago
Wed, Sep. 3 - Thu, Sep. 11
YYZ
Pearson Intl.
SDQ
Las Americas Intl.
CA $411 Roundtrip, found 2 days ago
CA $411
Roundtrip
found 2 days ago
Select Arajet flight, departing Wed, Sep. 3 from Pearson Intl. to Las Americas Intl., returning Thu, Sep. 11, priced at CA $411 found 2 days ago
OriginDestinationTravel datesFlights from*
EWRSan JuanOctober 21 to October 25CA $268
LGAMontego BayAugust 30 to September 6CA $349
LGASanto DomingoSeptember 6 to September 12CA $382
EWROranjestadOctober 16 to October 22CA $387
EWRMontego BayAugust 31 to September 6CA $423
JFKNassauSeptember 4 to September 7CA $425
EWRSanto DomingoSeptember 22 to October 1CA $445
EWRSantiago de los CaballerosSeptember 4 to September 11CA $453
BOSOranjestadSeptember 6 to September 14CA $461
JFKSanto DomingoNovember 9 to November 17CA $467
JFKSantiago de los CaballerosSeptember 4 to September 13CA $484
JFKMontego BaySeptember 23 to September 30CA $518
JFKPiarcoOctober 9 to October 13CA $540
JFKKingstonSeptember 12 to September 19CA $562
BOSNassauOctober 12 to October 17CA $633
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
FLLSanto DomingoAugust 10 to August 12CA $353
JFKSan JuanAugust 9 to August 16CA $504
MIAPiarcoAugust 8 to August 12CA $516
JFKSanto DomingoAugust 10 to August 17CA $593
YYZPunta CanaAugust 9 to August 23CA $658
EWRSanto DomingoAugust 10 to August 11CA $659
JFKPiarcoAugust 9 to August 13CA $719
EWRMontego BayAugust 8 to August 15CA $722
BOSNassauAugust 10 to August 17CA $811
YYZMontego BayAugust 10 to August 20CA $837
YYZSan JuanAugust 9 to September 20CA $896
EWRNassauAugust 8 to August 14CA $979
EWRKingstonAugust 9 to August 12CA $983
YYZKingstonAugust 10 to August 25CA $1,055
JFKOranjestadAugust 8 to August 19CA $1,235
*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

Sep 6 - Sep 13

7 night stay

Montreal (YUL) to Santo Domingo (SDQ)

American Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
Princess Senses The Mangrove Resort - Adults Only
4.0-star property

Princess Senses The Mangrove Resort - Adults Only

Aug 7 - Aug 14

7 night stay

Montreal (YMQ) to Montego Bay (MBJ)

American Airlines • Roundtrip • FirstClass
per person
found 1 day ago
Princess Grand Jamaica Resort - All Inclusive
4.5-star property

Princess Grand Jamaica Resort - All Inclusive

Sep 28 - Oct 5

7 night stay

Montreal (YMQ) to Montego Bay (MBJ)

United • Non-stop roundtrip • Coach
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! (1,006 reviews)
"Excellent location, most things were within walking distance. The premises are well kept, and clean. Rooms have the old San Juan feel but with modern touch, such as the remodeled bathrooms. We enjoyed our stay, and would recommend!"

Reviewed on Aug. 4, 2025

Hotel 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 Ocean Club Golf Course and Cable Beach are located nearby.
8.6/10 Excellent! (1,837 reviews)
"The staff is so friendly, the hotel was beautiful and super welcoming! I would 100% recommend and will be telling my family and friends about this place and will be my go to place when I go back!"

Reviewed on Aug. 4, 2025

British 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! (1,063 reviews)
"The area was very safe and walkable! A huge plus for us was that hotal was veryy close to old San Juan and how everything just seemed very accessible!!"

Reviewed on Aug. 1, 2025

Hotel 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! (1,403 reviews)
"Thank you for everything. The Atlantis exceeded our expectations. We will be taking back with us many happy memories!"

Reviewed on Jul. 28, 2025

The 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 $267. 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 September. 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 $267. 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 $267 and CA $1,235 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.