Flights To Caribbean - Cheap Flights Starting at CA $152

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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., Jun. 7 - Sat., Jun. 14
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $271 Roundtrip, found 1 hour ago
CA $271
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Sat., Jun. 7 from Pearson Intl. to Punta Cana Intl., returning Sat., Jun. 14, priced at CA $271 found 1 hour ago
Wed., Jun. 18 - Fri., Jun. 27
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $337 Roundtrip, just found
CA $337
Roundtrip
just found
Select Flair Airlines flight, departing Wed., Jun. 18 from Pearson Intl. to Norman Manley Intl., returning Fri., Jun. 27, priced at CA $337 just found
Fri., Jun. 13 - Tue., Jun. 17
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $349 Roundtrip, found 18 hours ago
CA $349
Roundtrip
found 18 hours ago
Select Arajet flight, departing Fri., Jun. 13 from Pearson Intl. to Punta Cana Intl., returning Tue., Jun. 17, priced at CA $349 found 18 hours ago
Sat., Jun. 7 - Wed., Jun. 18
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $351 Roundtrip, found 4 days ago
CA $351
Roundtrip
found 4 days ago
Select WestJet flight, departing Sat., Jun. 7 from Pearson Intl. to Punta Cana Intl., returning Wed., Jun. 18, priced at CA $351 found 4 days ago
Sun., May 11 - Thu., May 29
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $357 Roundtrip, found 7 hours ago
CA $357
Roundtrip
found 7 hours ago
Select WestJet flight, departing Sun., May 11 from Pearson Intl. to Lynden Pindling Intl., returning Thu., May 29, priced at CA $357 found 7 hours ago
Sat., May 3 - Thu., May 8
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $358 Roundtrip, found 4 hours ago
CA $358
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat., May 3 from Pearson Intl. to Luis Munoz Marin Intl., returning Thu., May 8, priced at CA $358 found 4 hours ago
Tue., Sep. 30 - Tue., Sep. 30
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $368 Roundtrip, just found
CA $368
Roundtrip
just found
Select WestJet flight, departing Tue., Sep. 30 from Pearson Intl. to Queen Beatrix Intl., returning Tue., Sep. 30, priced at CA $368 just found
Fri., Jul. 18 - Thu., Jul. 31
YYZ
Pearson Intl.
MBJ
Sir Donald Sangster Intl.
CA $372 Roundtrip, found 1 hour ago
CA $372
Roundtrip
found 1 hour ago
Select WestJet flight, departing Fri., Jul. 18 from Pearson Intl. to Sir Donald Sangster Intl., returning Thu., Jul. 31, priced at CA $372 found 1 hour ago
OriginDestinationTravel datesFlights from*
FLLOranjestadMay 24 to May 25CA $320
MIANassauJune 6 to June 11CA $375
FLLSantiago de los CaballerosJune 13 to June 16CA $438
JFKSantiago de los CaballerosJune 1 to June 21CA $439
BOSPunta CanaMay 16 to May 24CA $440
JFKSanto DomingoMay 16 to May 18CA $450
JFKNassauJune 1 to June 7CA $499
EWRKingstonMay 19 to May 28CA $500
EWRKingstonMay 19 to May 28CA $500
JFKPiarcoJune 6 to June 13CA $544
JFKPiarcoJune 6 to June 13CA $544
EWRPiarcoJune 5 to June 8CA $560
PHLMontego BayMay 24 to May 31CA $592
JFKKingstonMay 19 to May 28CA $603
BOSPiarcoMay 17 to May 21CA $690
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
FLLPunta CanaMay 3 to May 4CA $308
EWRSan JuanMay 3 to May 6CA $336
MIANassauMay 3 to May 7CA $415
JFKSantiago de los CaballerosMay 4 to May 9CA $579
JFKSantiago de los CaballerosMay 4 to May 9CA $579
EWRPiarcoMay 3 to May 10CA $591
EWRPiarcoMay 3 to May 10CA $591
LGAKingstonMay 3 to May 5CA $658
EWRKingstonMay 3 to May 5CA $696
JFKPiarcoMay 3 to May 10CA $708
JFKPunta CanaMay 3 to May 6CA $713
JFKPunta CanaMay 3 to May 6CA $713
JFKMontego BayMay 3 to May 7CA $734
YYZMontego BayMay 4 to May 11CA $856
JFKKingstonMay 3 to May 5CA $889
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at The Palms
3.0-star property

Ocho Rios Villa at The Palms

May 2 - May 8

6 night stay

Toronto (YTO) to Montego Bay (MBJ)

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

Jun. 7 - Jun. 14

7 night stay

Hamilton (YHM) to Montego Bay (MBJ)

Air Canada • Non-stop roundtrip • Coach
per person
found 1 day ago
Princess Grand Jamaica Resort - All Inclusive
4.5-star property

Princess Grand Jamaica Resort - All Inclusive

Jul. 13 - Jul. 20

7 night stay

Toronto (YTO) to Montego Bay (MBJ)

United • Non-stop • Coach

Montego Bay (MBJ) to Toronto (YTO)

Air Transat • Non-stop • 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.
8.6/10 Excellent! (1,000 reviews)
"El Convento is always a great choice for Old San Juan. Our room this time did have a disagreeable view of the squalid property’s roof which was next door. Management could not move us but were very apologetic and sincere in taking our concerns seriously. We always stay at El Convento."

Reviewed on Apr. 27, 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 Junkanoo Beach and Aquaventure are located nearby.
8.4/10 Very Good! (1,530 reviews)
"The property is great but the area surrounding the property shuts down once cruise ships leave port which gives the impression they cater to the ship clientele needs."

Reviewed on Apr. 28, 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.
8.8/10 Excellent! (914 reviews)
"Loved Michael and Christian at the bar. They were kind, respectful and very attentive."

Reviewed on Apr. 30, 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 Aquaventure and Cabbage Beach are located nearby.
8.8/10 Excellent! (1,323 reviews)
"Beautiful beach, clean, many pools, room with kitchen"

Reviewed on Apr. 29, 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 $271. 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 June. 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 $271. 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 $271 and CA $889 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.