Flights To Caribbean - Cheap Flights Starting at CA $155

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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.

Wed., 26 Feb. - Wed., 5 Mar.
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $331 Roundtrip, found 8 hours ago
CA $331
Roundtrip
found 8 hours ago
Select Flair Airlines flight, departing Wed., 26 Feb. from Pearson Intl. to Norman Manley Intl., returning Wed., 5 Mar., priced at CA $331 found 8 hours ago
Wed., 5 Feb. - Wed., 12 Feb.
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $344 Roundtrip, found 3 days ago
CA $344
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed., 5 Feb. from Pearson Intl. to Luis Munoz Marin Intl., returning Wed., 12 Feb., priced at CA $344 found 3 days ago
Fri., 3 Oct. - Fri., 10 Oct.
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $360 Roundtrip, found 6 hours ago
CA $360
Roundtrip
found 6 hours ago
Select Arajet flight, departing Fri., 3 Oct. from Pearson Intl. to Punta Cana Intl., returning Fri., 10 Oct., priced at CA $360 found 6 hours ago
Wed., 16 Apr. - Thu., 19 Jun.
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $368 Roundtrip, found 4 days ago
CA $368
Roundtrip
found 4 days ago
Select WestJet flight, departing Wed., 16 Apr. from Pearson Intl. to Queen Beatrix Intl., returning Thu., 19 Jun., priced at CA $368 found 4 days ago
Sun., 30 Mar. - Sun., 20 Apr.
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $393 Roundtrip, found 6 days ago
CA $393
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sun., 30 Mar. from Pearson Intl. to Luis Munoz Marin Intl., returning Sun., 20 Apr., priced at CA $393 found 6 days ago
Sat., 22 Feb. - Fri., 28 Feb.
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $407 Roundtrip, found 1 day ago
CA $407
Roundtrip
found 1 day ago
Select United flight, departing Sat., 22 Feb. from Pearson Intl. to Luis Munoz Marin Intl., returning Fri., 28 Feb., priced at CA $407 found 1 day ago
Tue., 15 Apr. - Wed., 23 Apr.
YYZ
Pearson Intl.
SDQ
Las Americas Intl.
CA $415 Roundtrip, found 6 days ago
CA $415
Roundtrip
found 6 days ago
Select Arajet flight, departing Tue., 15 Apr. from Pearson Intl. to Las Americas Intl., returning Wed., 23 Apr., priced at CA $415 found 6 days ago
Tue., 1 Apr. - Tue., 8 Apr.
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $420 Roundtrip, found 8 hours ago
CA $420
Roundtrip
found 8 hours ago
Select WestJet flight, departing Tue., 1 Apr. from Pearson Intl. to Lynden Pindling Intl., returning Tue., 8 Apr., priced at CA $420 found 8 hours ago
OriginDestinationTravel datesFlights from*
PHLSan JuanMarch 1 to March 6CA $219
JFKSan JuanMarch 3 to March 7CA $229
MIASanto DomingoApril 11 to April 18CA $353
FLLSanto DomingoMarch 4 to March 7CA $377
EWRKingstonMarch 12 to March 19CA $419
EWRKingstonMarch 12 to March 19CA $419
JFKOranjestadMarch 9 to March 17CA $445
EWRSanto DomingoMarch 1 to March 8CA $457
BOSNassauMarch 22 to April 3CA $462
EWRSantiago de los CaballerosFebruary 23 to February 27CA $473
JFKKingstonApril 2 to April 9CA $519
BOSSantiago de los CaballerosFebruary 28 to March 9CA $528
PHLMontego BayMarch 18 to March 23CA $597
BOSKingstonApril 9 to April 17CA $709
BOSPiarcoMarch 31 to April 8CA $783
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
EWRSan JuanFebruary 9 to February 14CA $187
EWRSan JuanFebruary 9 to February 14CA $187
BOSSan JuanFebruary 8 to February 12CA $212
FLLSanto DomingoFebruary 9 to February 13CA $355
FLLOranjestadFebruary 9 to February 22CA $373
FLLPunta CanaFebruary 8 to February 15CA $461
EWROranjestadFebruary 9 to February 18CA $500
JFKKingstonFebruary 9 to February 11CA $525
BOSSanto DomingoFebruary 9 to February 15CA $544
JFKOranjestadFebruary 7 to February 11CA $647
EWRMontego BayFebruary 7 to February 16CA $727
BOSNassauFebruary 9 to February 16CA $767
EWRNassauFebruary 7 to February 10CA $815
EWRNassauFebruary 7 to February 10CA $815
JFKNassauFebruary 7 to February 10CA $1,064
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Retreat Plantation House
3.0-star property

Retreat Plantation House

Apr. 23 - Apr. 30

7 night stay

Toronto (YYZ) to Montego Bay (MBJ)

Flair Airlines • Roundtrip • Coach
per person
found 1 day ago
The Signature Level At Grand Palladium Lady Hamilton Resort & Spa
4.5-star property

The Signature Level At Grand Palladium Lady Hamilton Resort & Spa

Mar. 1 - Mar. 8

7 night stay

Winnipeg (YWG) to Montego Bay (MBJ)

WestJet • Roundtrip • Coach
per person
found 1 day ago
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Mar. 22 - Mar. 29

7 night stay

Winnipeg (YWG) to Montego Bay (MBJ)

WestJet • Coach

Montego Bay (MBJ) to Winnipeg (YWG)

Air Canada • Coach
per person
found 22 hours ago
Don't see what you're looking for?
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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! (1,008 reviews)
"Lovely little boutique hotel!"

Reviewed on 31 Jan. 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 Cabbage Beach and Cable Beach are located nearby.
8.4/10 Very Good! (1,215 reviews)
"The property is downtown and central of nassau. Parking is convenient."

Reviewed on 2 Feb. 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! (710 reviews)
"Excellent"

Reviewed on 31 Jan. 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 Cable Beach and Aquaventure are located nearby.
8.8/10 Excellent! (1,137 reviews)
"Our stay was very enjoyable. Staff was amazing."

Reviewed on 3 Feb. 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 $187. 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 February. 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 $187. 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 $187 and CA $1,064 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.