Flights To Caribbean - Cheap Flights Starting at CA $176

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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.

Mon, Nov. 17 - Tue, Nov. 18
YUL
Pierre Elliott Trudeau Intl.
SJU
Luis Munoz Marin Intl.
CA $344 Roundtrip, found 2 days ago
CA $344
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Nov. 17 from Pierre Elliott Trudeau Intl. to Luis Munoz Marin Intl., returning Tue, Nov. 18, priced at CA $344 found 2 days ago
Sun, Nov. 2 - Fri, Nov. 7
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $348 Roundtrip, found 1 day ago
CA $348
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Nov. 2 from Pearson Intl. to Luis Munoz Marin Intl., returning Fri, Nov. 7, priced at CA $348 found 1 day ago
Sat, Sep. 20 - Sat, Sep. 27
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $367 Roundtrip, just found
CA $367
Roundtrip
just found
Select Flair Airlines flight, departing Sat, Sep. 20 from Pearson Intl. to Punta Cana Intl., returning Sat, Sep. 27, priced at CA $367 just found
Tue, Nov. 4 - Wed, Nov. 5
YYZ
Pearson Intl.
AUA
Queen Beatrix Intl.
CA $394 Roundtrip, found 20 hours ago
CA $394
Roundtrip
found 20 hours ago
Select WestJet flight, departing Tue, Nov. 4 from Pearson Intl. to Queen Beatrix Intl., returning Wed, Nov. 5, priced at CA $394 found 20 hours ago
Wed, Nov. 26 - Sun, Nov. 30
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $414 Roundtrip, found 2 days ago
CA $414
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Wed, Nov. 26 from Pearson Intl. to Lynden Pindling Intl., returning Sun, Nov. 30, priced at CA $414 found 2 days ago
Thu, Sep. 18 - Thu, Sep. 25
YUL
Pierre Elliott Trudeau Intl.
PUJ
Punta Cana Intl.
CA $416 Roundtrip, found 9 hours ago
CA $416
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Thu, Sep. 18 from Pierre Elliott Trudeau Intl. to Punta Cana Intl., returning Thu, Sep. 25, priced at CA $416 found 9 hours ago
Wed, Nov. 12 - Wed, Nov. 26
YUL
Pierre Elliott Trudeau Intl.
AUA
Queen Beatrix Intl.
CA $437 Roundtrip, found 2 days ago
CA $437
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Nov. 12 from Pierre Elliott Trudeau Intl. to Queen Beatrix Intl., returning Wed, Nov. 26, priced at CA $437 found 2 days ago
Fri, Oct. 3 - Fri, Oct. 10
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $443 Roundtrip, just found
CA $443
Roundtrip
just found
Select Flair Airlines flight, departing Fri, Oct. 3 from Pearson Intl. to Norman Manley Intl., returning Fri, Oct. 10, priced at CA $443 just found
OriginDestinationTravel datesFlights from*
FLLSanto DomingoSeptember 6 to September 14CA $285
FLLMontego BaySeptember 6 to September 10CA $295
FLLSantiago de los CaballerosSeptember 6 to September 8CA $299
MIAPunta CanaSeptember 27 to October 2CA $316
MIAPiarcoSeptember 18 to September 27CA $403
FLLOranjestadSeptember 20 to September 27CA $409
JFKNassauOctober 25 to November 1CA $425
EWRSantiago de los CaballerosSeptember 22 to September 26CA $462
JFKSantiago de los CaballerosSeptember 4 to September 11CA $466
BOSOranjestadSeptember 22 to September 29CA $489
JFKMontego BaySeptember 6 to September 12CA $512
JFKPiarcoSeptember 7 to September 13CA $542
JFKPiarcoSeptember 7 to September 13CA $542
BOSKingstonSeptember 26 to October 3CA $579
EWRKingstonSeptember 18 to September 23CA $579
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
FLLKingstonAugust 23 to August 29CA $349
PHLPunta CanaAugust 23 to August 30CA $404
FLLSan JuanAugust 22 to August 25CA $425
MIANassauAugust 23 to August 27CA $477
FLLOranjestadAugust 23 to August 30CA $491
LGASanto DomingoAugust 23 to August 25CA $512
EWRSanto DomingoAugust 23 to August 25CA $639
JFKSan JuanAugust 22 to August 25CA $687
BOSMontego BayAugust 22 to August 29CA $758
YYZPunta CanaAugust 23 to August 30CA $761
JFKPiarcoAugust 22 to August 25CA $767
JFKMontego BayAugust 24 to August 30CA $884
JFKNassauAugust 22 to August 25CA $897
EWRMontego BayAugust 24 to September 1CA $908
YYZSan JuanAugust 23 to August 26CA $1,321
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Princess Grand Jamaica Resort - All Inclusive
4.5-star property

Princess Grand Jamaica Resort - All Inclusive

Sep 9 - Sep 16

7 night stay

Montreal (YUL) 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

Sep 11 - Sep 18

7 night stay

Montreal (YUL) to Montego Bay (MBJ)

Delta • Non-stop • Coach

Montego Bay (MBJ) to Montreal (YUL)

American Airlines • Non-stop • Coach
per person
found 1 day ago
Coral Costa Caribe Beach Resort - All Inclusive
4.0-star property

Coral Costa Caribe Beach Resort - All Inclusive

Oct 24 - Oct 31

7 night stay

Montreal (YUL) to Santo Domingo (SDQ)

American Airlines • Non-stop roundtrip • Coach
per person
found 1 day 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.
8.8/10 Excellent! (1,005 reviews)
"So kind. Thanks!"

Reviewed on Aug. 15, 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 Cable Beach are located nearby.
8.6/10 Excellent! (1,886 reviews)
"Antonya at the front desk was excellent"

Reviewed on Aug. 14, 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! (1,097 reviews)
"Been here several times before and the staff as usual very professional and helpful. Great hotel to stay for cruise ship vacations. Highly recommend it. Our favorite hotel in San Juan. Thank you."

Reviewed on Aug. 16, 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! (1,405 reviews)
"Everything was great . But would love to to have some fish or shrimp without paying a fortune ."

Reviewed on Aug. 16, 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 $285. 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 $285. 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 $285 and CA $1,321 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.