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.

Sat, Sep 27 - Sat, Sep 27
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $267 Roundtrip, found 5 days ago
CA $267
Roundtrip
found 5 days ago
Select Flair Airlines flight, departing Sat, Sep 27 from Pearson Intl. to Punta Cana Intl., returning Sat, Sep 27, priced at CA $267 found 5 days ago
Sat, Oct 4 - Thu, Oct 9
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $346 Roundtrip, just found
CA $346
Roundtrip
just found
Select WestJet flight, departing Sat, Oct 4 from Pearson Intl. to Lynden Pindling Intl., returning Thu, Oct 9, priced at CA $346 just found
Mon, Nov 10 - Wed, Nov 19
YUL
Pierre Elliott Trudeau Intl.
SJU
Luis Munoz Marin Intl.
CA $352 Roundtrip, found 18 hours ago
CA $352
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Mon, Nov 10 from Pierre Elliott Trudeau Intl. to Luis Munoz Marin Intl., returning Wed, Nov 19, priced at CA $352 found 18 hours ago
Fri, Oct 17 - Wed, Oct 29
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $373 Roundtrip, found 1 day ago
CA $373
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct 17 from Pearson Intl. to Luis Munoz Marin Intl., returning Wed, Oct 29, priced at CA $373 found 1 day ago
Fri, Nov 7 - Mon, Nov 17
YUL
Pierre Elliott Trudeau Intl.
NAS
Lynden Pindling Intl.
CA $385 Roundtrip, found 2 days ago
CA $385
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 7 from Pierre Elliott Trudeau Intl. to Lynden Pindling Intl., returning Mon, Nov 17, priced at CA $385 found 2 days ago
Mon, Nov 3 - Fri, Nov 7
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $387 Roundtrip, found 4 hours ago
CA $387
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 $387 found 4 hours ago
Fri, Oct 24 - Fri, Oct 31
YUL
Pierre Elliott Trudeau Intl.
PUJ
Punta Cana Intl.
CA $398 Roundtrip, found 7 hours ago
CA $398
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, Oct 24 from Pierre Elliott Trudeau Intl. to Punta Cana Intl., returning Fri, Oct 31, priced at CA $398 found 7 hours ago
Wed, Oct 1 - Wed, Oct 8
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $428 Roundtrip, found 8 hours ago
CA $428
Roundtrip
found 8 hours ago
Select Flair Airlines flight, departing Wed, Oct 1 from Pearson Intl. to Norman Manley Intl., returning Wed, Oct 8, priced at CA $428 found 8 hours ago
OriginDestinationTravel datesFlights from*
EWRSan JuanOctober 14 to October 23CA $271
JFKPunta CanaOctober 19 to October 24CA $360
JFKPunta CanaOctober 19 to October 24CA $360
EWRSanto DomingoNovember 7 to November 18CA $366
EWRSanto DomingoNovember 7 to November 18CA $366
JFKNassauOctober 12 to October 16CA $429
JFKSantiago de los CaballerosOctober 14 to October 21CA $437
JFKSanto DomingoOctober 13 to October 17CA $437
EWRMontego BayOctober 27 to November 2CA $442
JFKPiarcoOctober 3 to October 9CA $461
JFKPiarcoOctober 3 to October 9CA $461
JFKMontego BayOctober 27 to November 2CA $500
JFKKingstonOctober 31 to November 3CA $530
JFKKingstonOctober 31 to November 3CA $530
EWRKingstonDecember 5 to December 28CA $822
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
FLLSanto DomingoSeptember 20 to September 24CA $283
JFKSan JuanSeptember 21 to September 30CA $302
JFKSan JuanSeptember 21 to September 30CA $302
EWRSan JuanSeptember 21 to September 25CA $423
YYZKingstonSeptember 20 to September 27CA $459
MIANassauSeptember 20 to September 27CA $471
EWRPunta CanaSeptember 21 to September 24CA $503
BOSPunta CanaSeptember 21 to September 24CA $546
JFKPunta CanaSeptember 21 to September 24CA $578
JFKPiarcoSeptember 20 to September 23CA $585
JFKPiarcoSeptember 20 to September 23CA $585
YYZPiarcoSeptember 21 to October 11CA $637
MIAPiarcoSeptember 21 to October 5CA $675
BOSSantiago de los CaballerosSeptember 20 to September 22CA $733
YYZOranjestadSeptember 21 to September 24CA $804
*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 12 - Oct 19

7 night stay

Ottawa (YOW) to Santo Domingo (SDQ)

United • Non-stop • Coach

Santo Domingo (SDQ) to Ottawa (YOW)

WestJet • Non-stop • Coach
Price was CA $2,682, price is now CA $1,076 per person
CA $1,076
per person
found 1 day ago
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Nov 20 - Nov 25

5 night stay

Winnipeg (YWG) to Montego Bay (MBJ)

WestJet • Non-stop roundtrip • Coach
Price was CA $3,749, price is now CA $1,227 per person
CA $1,227
per person
found 1 day ago
Ocho Rios Villa at The Palms
3.0-star property

Ocho Rios Villa at The Palms

Nov 7 - Nov 14

7 night stay

Toronto (YYZ) to Montego Bay (MBJ)

United • Non-stop roundtrip • Coach
Price was CA $3,803, price is now CA $1,550 per person
CA $1,550
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! (1,003 reviews)
"I booked Hotel El Convento for an after cruise stay for my husband, myself, my two adult kids and their spouses and we couldn’t be happier with the experience. The staff couldn’t wait to help us with all of our travel needs and our stay here was the highlight of a two week 50th anniversary celebration! ..."

Reviewed on Sep 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! (1,950 reviews)
Nice place in downtown Nassau
"I stayed at the British Colonial on a recent business trip and I have nothing but good things to say about the property. It’s well located and the rooms are comfortable. The gym is decent too. Food is a little on the pricey side, but this being The Bahamas, that’s to be expected."

Reviewed on Sep 16, 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! (1,158 reviews)
"Fantastic staff. Hotel is beautifully maintained. Close to old San Juan shopping and tourism! We loved our stay."

Reviewed on Sep 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! (1,416 reviews)
Love The Cove
"We stayed at The Cove and loved the high ceilings, beautiful balcony with two chairs and a table, huge marble bathroom, gorgeous beaches and swimming pools!"

Reviewed on Sep 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 $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 $822 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.