Flights To Caribbean - Cheap Flights Starting at CA $167

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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. 6 - Sat., Sep. 13
YYZ
Pearson Intl.
PUJ
Punta Cana Intl.
CA $271 Roundtrip, just found
CA $271
Roundtrip
just found
Select Flair Airlines flight, departing Sat., Sep. 6 from Pearson Intl. to Punta Cana Intl., returning Sat., Sep. 13, priced at CA $271 just found
Wed., Nov. 12 - Tue., Nov. 25
YYZ
Pearson Intl.
SJU
Luis Munoz Marin Intl.
CA $327 Roundtrip, found 2 days ago
CA $327
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed., Nov. 12 from Pearson Intl. to Luis Munoz Marin Intl., returning Tue., Nov. 25, priced at CA $327 found 2 days ago
Sat., Jul. 12 - Fri., Jul. 18
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $337 Roundtrip, just found
CA $337
Roundtrip
just found
Select Flair Airlines flight, departing Sat., Jul. 12 from Pearson Intl. to Norman Manley Intl., returning Fri., Jul. 18, priced at CA $337 just found
Tue., Nov. 4 - Wed., Nov. 5
YUL
Pierre Elliott Trudeau Intl.
SJU
Luis Munoz Marin Intl.
CA $357 Roundtrip, found 6 days ago
CA $357
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue., Nov. 4 from Pierre Elliott Trudeau Intl. to Luis Munoz Marin Intl., returning Wed., Nov. 5, priced at CA $357 found 6 days ago
Wed., Jul. 2 - Wed., Jul. 9
YYZ
Pearson Intl.
NAS
Lynden Pindling Intl.
CA $405 Roundtrip, found 9 hours ago
CA $405
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Wed., Jul. 2 from Pearson Intl. to Lynden Pindling Intl., returning Wed., Jul. 9, priced at CA $405 found 9 hours ago
Tue., Aug. 19 - Fri., Aug. 29
YUL
Pierre Elliott Trudeau Intl.
AUA
Queen Beatrix Intl.
CA $406 Roundtrip, found 3 days ago
CA $406
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue., Aug. 19 from Pierre Elliott Trudeau Intl. to Queen Beatrix Intl., returning Fri., Aug. 29, priced at CA $406 found 3 days ago
Wed., Nov. 5 - Thu., Nov. 20
YUL
Pierre Elliott Trudeau Intl.
PUJ
Punta Cana Intl.
CA $409 Roundtrip, found 5 days ago
CA $409
Roundtrip
found 5 days ago
Select Arajet flight, departing Wed., Nov. 5 from Pierre Elliott Trudeau Intl. to Punta Cana Intl., returning Thu., Nov. 20, priced at CA $409 found 5 days ago
Wed., Jul. 9 - Tue., Jul. 15
YUL
Pierre Elliott Trudeau Intl.
NAS
Lynden Pindling Intl.
CA $410 Roundtrip, found 2 days ago
CA $410
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed., Jul. 9 from Pierre Elliott Trudeau Intl. to Lynden Pindling Intl., returning Tue., Jul. 15, priced at CA $410 found 2 days ago
OriginDestinationTravel datesFlights from*
PHLMontego BayJuly 19 to July 23CA $359
FLLOranjestadJuly 10 to July 17CA $362
FLLPiarcoJuly 3 to September 14CA $412
JFKMontego BaySeptember 7 to September 12CA $420
JFKNassauJuly 19 to July 26CA $448
BOSMontego BayJuly 12 to July 12CA $454
LGASantiago de los CaballerosJuly 5 to July 9CA $458
EWRKingstonJuly 2 to July 9CA $552
PHLSanto DomingoJuly 23 to July 30CA $617
BOSKingstonJuly 11 to July 16CA $688
MIAKingstonJuly 3 to July 7CA $779
LHRNassauSeptember 6 to September 14CA $1,103
LGWPunta CanaSeptember 29 to October 8CA $1,125
LGWPiarcoJuly 4 to July 8CA $1,385
LGWSanto DomingoAugust 27 to August 27CA $2,074
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
FLLMontego BayJune 20 to June 27CA $326
JFKSan JuanJune 21 to July 5CA $329
JFKSan JuanJune 21 to July 5CA $329
EWRSan JuanJune 21 to June 22CA $510
JFKMontego BayJune 22 to August 30CA $534
JFKMontego BayJune 22 to August 30CA $534
LGANassauJune 20 to June 21CA $582
JFKPunta CanaJune 20 to June 27CA $583
JFKPunta CanaJune 20 to June 27CA $583
EWRSanto DomingoJune 20 to June 29CA $586
EWRSanto DomingoJune 20 to June 29CA $586
EWRKingstonJune 20 to June 21CA $621
JFKKingstonJune 21 to July 14CA $734
JFKNassauJune 21 to June 26CA $788
BOSOranjestadJune 20 to June 24CA $1,029
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Alamanda Cottage at Serenity
3.0-star property

Alamanda Cottage at Serenity

Aug 30 - Sep 6

7 night stay

Montreal (YUL) to Montego Bay (MBJ)

United • 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

Sep 1 - Sep 7

6 night stay

Montreal (YUL) to Montego Bay (MBJ)

United • 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 21 - Jun 28

7 night stay

Montreal (YUL) to Montego Bay (MBJ)

American Airlines • Non-stop • Coach

Montego Bay (MBJ) to Montreal (YUL)

WestJet • Non-stop • 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)
". everything was great specially the location was walking distance from everything will consider staying there again in the future."

Reviewed on Jun. 17, 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 Aquaventure and Ocean Club Golf Course are located nearby.
8.6/10 Excellent! (1,666 reviews)
"Had a blast and was a very nice hotel"

Reviewed on Jun. 16, 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! (978 reviews)
"friendly staff and very clean rooms and restrooms"

Reviewed on Jun. 18, 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 Ocean Club Golf Course are located nearby.
8.8/10 Excellent! (1,375 reviews)
"Everything was wonderful- 2 areas of opportunity were 1.) the water in the shower had a strong treated smell 2.) the air conditioner in the master bedroom stayed a little too warm."

Reviewed on Jun. 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 $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 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 $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 $2,074 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.