Flights To Caribbean - Cheap Flights Starting at CA $139

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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.

Sun, Nov 23 - Tue, Dec 16
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $330 Roundtrip, found 9 hours ago
CA $330
Roundtrip
found 9 hours ago
Select Flair Airlines flight, departing Sun, Nov 23 from Pearson Intl. to Punta Cana Intl., returning Tue, Dec 16, priced at CA $330 found 9 hours ago
Wed, Apr 15 - Sat, Apr 18
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $333 Roundtrip, found 6 days ago
CA $333
Roundtrip
found 6 days ago
Select Arajet flight, departing Wed, Apr 15 from Pearson Intl. to Punta Cana Intl., returning Sat, Apr 18, priced at CA $333 found 6 days ago
Mon, Nov 17 - Wed, Nov 26
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $347 Roundtrip, just found
CA $347
Roundtrip
just found
Select WestJet flight, departing Mon, Nov 17 from Pearson Intl. to Lynden Pindling Intl., returning Wed, Nov 26, priced at CA $347 just found
Sun, Nov 16 - Fri, Nov 21
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $348 Roundtrip, just found
CA $348
Roundtrip
just found
Select WestJet flight, departing Sun, Nov 16 from Pearson Intl. to Lynden Pindling Intl., returning Fri, Nov 21, priced at CA $348 just found
Mon, Nov 3 - Fri, Nov 7
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $359 Roundtrip, just found
CA $359
Roundtrip
just found
Select WestJet flight, departing Mon, Nov 3 from Pearson Intl. to Queen Beatrix Intl., returning Fri, Nov 7, priced at CA $359 just found
Fri, Nov 28 - Wed, Dec 3
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $377 Roundtrip, found 8 hours ago
CA $377
Roundtrip
found 8 hours ago
Select Air Transat flight, departing Fri, Nov 28 from Pearson Intl. to Lynden Pindling Intl., returning Wed, Dec 3, priced at CA $377 found 8 hours ago
Sun, Feb 22 - Thu, Mar 5
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $384 Roundtrip, found 16 hours ago
CA $384
Roundtrip
found 16 hours ago
Select United flight, departing Sun, Feb 22 from Pearson Intl. to Luis Munoz Marin Intl., returning Thu, Mar 5, priced at CA $384 found 16 hours ago
Tue, Mar 10 - Wed, Mar 11
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $392 Roundtrip, found 16 hours ago
CA $392
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Tue, Mar 10 from Pearson Intl. to Luis Munoz Marin Intl., returning Wed, Mar 11, priced at CA $392 found 16 hours ago
OriginDestinationTravel datesFlights from*
LGAMontego BayNovember 2 to November 6CA $347
EWRSanto DomingoJanuary 22 to January 28CA $372
EWRPunta CanaNovember 8 to November 14CA $397
JFKPunta CanaNovember 18 to November 23CA $397
JFKNassauNovember 3 to November 6CA $421
JFKNassauNovember 3 to November 6CA $421
JFKSanto DomingoNovember 4 to November 8CA $446
JFKSantiago de los CaballerosNovember 12 to November 27CA $446
EWRMontego BayNovember 10 to November 15CA $447
JFKPiarcoNovember 6 to November 12CA $467
JFKPiarcoNovember 6 to November 12CA $467
JFKMontego BayNovember 15 to November 22CA $498
LGAKingstonNovember 8 to November 12CA $525
JFKKingstonNovember 8 to November 12CA $537
EWRKingstonNovember 8 to November 12CA $567
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKSan JuanOctober 25 to October 31CA $290
JFKSan JuanOctober 25 to October 31CA $290
EWRSan JuanOctober 26 to October 29CA $351
FLLKingstonOctober 24 to October 26CA $429
BOSSan JuanOctober 24 to October 27CA $486
BOSOranjestadOctober 26 to November 2CA $521
JFKMontego BayOctober 25 to November 1CA $563
JFKMontego BayOctober 25 to November 1CA $563
JFKNassauOctober 24 to November 1CA $577
JFKNassauOctober 24 to November 1CA $577
JFKKingstonOctober 25 to October 31CA $609
JFKKingstonOctober 25 to October 31CA $609
JFKPiarcoOctober 24 to October 31CA $700
JFKPiarcoOctober 24 to October 31CA $700
EWRPiarcoOctober 24 to October 31CA $701
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel
4.5-star property

Ola Boutique Hotel

Jan 7 - Jan 14

7 night stay

Calgary (YYC) to San Juan (SJU)

United • Roundtrip • Coach
Price was CA $3,026, price is now CA $1,308 per person
CA $1,308
per person
found 11 hours ago
Sunset at the Palms Resort - Adults Only - All Inclusive
4.5-star property

Sunset at the Palms Resort - Adults Only - All Inclusive

Jan 6 - Jan 13

7 night stay

Ottawa (YOW) to Montego Bay (MBJ)

WestJet • Non-stop roundtrip • Coach
Price was CA $7,904, price is now CA $2,973 per person
CA $2,973
per person
found 1 day ago
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Dec 9 - Dec 16

7 night stay

Ottawa (YOW) to Montego Bay (MBJ)

United • Non-stop roundtrip • Coach
Price was CA $3,458, price is now CA $1,470 per person
CA $1,470
per person
found 10 hours 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! (1,008 reviews)
"Property was clean and staff was very professional"

Reviewed on Oct 14, 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! (1,985 reviews)
"yes"

Reviewed on Oct 12, 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! (1,205 reviews)
"Great hotel!"

Reviewed on Oct 15, 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! (1,433 reviews)
"Most facilities closed, lazy river wasn’t working and the signature slide, leap of faith was closed. This could have been any other resort."

Reviewed on Oct 15, 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 $290. 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 November. 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 $290. 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 $290 and CA $701 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.