Flights To Caribbean - Cheap Flights Starting at CA $99

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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., Apr. 28 - Sat., May 3
EWR
Newark Liberty Intl. Airport
SJU
Luis Munoz Marin Intl.
CA $259 Roundtrip, found 6 days ago
CA $259
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon., Apr. 28 from Newark Liberty Intl. Airport to Luis Munoz Marin Intl., returning Sat., May 3, priced at CA $259 found 6 days ago
Sun., May 4 - Sun., May 11
JFK
John F. Kennedy Intl.
SJU
Luis Munoz Marin Intl.
CA $267 Roundtrip, found 6 days ago
CA $267
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sun., May 4 from John F. Kennedy Intl. to Luis Munoz Marin Intl., returning Sun., May 11, priced at CA $267 found 6 days ago
Thu., Sep. 25 - Thu., Oct. 9
EWR
Newark Liberty Intl. Airport
SDQ
Las Americas Intl.
CA $417 Roundtrip, found 5 days ago
CA $417
Roundtrip
found 5 days ago
Select Arajet flight, departing Thu., Sep. 25 from Newark Liberty Intl. Airport to Las Americas Intl., returning Thu., Oct. 9, priced at CA $417 found 5 days ago
Fri., May 9 - Thu., May 15
EWR
Newark Liberty Intl. Airport
PUJ
Punta Cana Intl.
CA $417 Roundtrip, found 6 days ago
CA $417
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Fri., May 9 from Newark Liberty Intl. Airport to Punta Cana Intl., returning Thu., May 15, priced at CA $417 found 6 days ago
Tue., Sep. 16 - Tue., Sep. 23
EWR
Newark Liberty Intl. Airport
MBJ
Sir Donald Sangster Intl.
CA $421 Roundtrip, found 2 days ago
CA $421
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue., Sep. 16 from Newark Liberty Intl. Airport to Sir Donald Sangster Intl., returning Tue., Sep. 23, priced at CA $421 found 2 days ago
Fri., Jun. 6 - Sat., Jun. 21
YUL
Pierre Elliott Trudeau Intl.
PUJ
Punta Cana Intl.
CA $422 Roundtrip, found 18 hours ago
CA $422
Roundtrip
found 18 hours ago
Select Arajet flight, departing Fri., Jun. 6 from Pierre Elliott Trudeau Intl. to Punta Cana Intl., returning Sat., Jun. 21, priced at CA $422 found 18 hours ago
Tue., Apr. 29 - Wed., May 7
YUL
Pierre Elliott Trudeau Intl.
AUA
Queen Beatrix Intl.
CA $437 Roundtrip, found 1 day ago
CA $437
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue., Apr. 29 from Pierre Elliott Trudeau Intl. to Queen Beatrix Intl., returning Wed., May 7, priced at CA $437 found 1 day ago
Thu., May 1 - Wed., May 7
JFK
John F. Kennedy Intl.
SDQ
Las Americas Intl.
CA $453 Roundtrip, found 6 days ago
CA $453
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu., May 1 from John F. Kennedy Intl. to Las Americas Intl., returning Wed., May 7, priced at CA $453 found 6 days ago
Thu., May 29 - Thu., Jun. 5
EWR
Newark Liberty Intl. Airport
AUA
Queen Beatrix Intl.
CA $454 Roundtrip, found 2 days ago
CA $454
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu., May 29 from Newark Liberty Intl. Airport to Queen Beatrix Intl., returning Thu., Jun. 5, priced at CA $454 found 2 days ago
Tue., Jul. 22 - Tue., Jul. 29
JFK
John F. Kennedy Intl.
NAS
Lynden Pindling Intl.
CA $461 Roundtrip, found 6 days ago
CA $461
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue., Jul. 22 from John F. Kennedy Intl. to Lynden Pindling Intl., returning Tue., Jul. 29, priced at CA $461 found 6 days ago
Wed., Apr. 30 - Wed., May 7
YUL
Pierre Elliott Trudeau Intl.
NAS
Lynden Pindling Intl.
CA $468 Roundtrip, found 5 days ago
CA $468
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed., Apr. 30 from Pierre Elliott Trudeau Intl. to Lynden Pindling Intl., returning Wed., May 7, priced at CA $468 found 5 days ago
OriginDestinationTravel datesFlights from*
FLLKingstonMay 3 to May 7CA $346
FLLSantiago de los CaballerosMay 1 to May 4CA $407
BOSPunta CanaApril 30 to May 7CA $429
BOSKingstonMay 5 to May 14CA $443
JFKSantiago de los CaballerosMay 10 to May 17CA $476
JFKSantiago de los CaballerosMay 10 to May 17CA $476
FLLPiarcoJuly 13 to August 1CA $479
EWRKingstonApril 28 to May 6CA $501
EWRKingstonApril 28 to May 6CA $501
EWRSantiago de los CaballerosMay 10 to May 17CA $510
JFKKingstonMay 7 to May 11CA $534
JFKPiarcoMay 10 to May 17CA $557
JFKPiarcoMay 10 to May 17CA $557
EWRPiarcoMay 10 to May 17CA $603
MIAWest EndApril 23 to April 27CA $744
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MIASan JuanApril 13 to April 22CA $157
FLLSan JuanApril 13 to April 22CA $240
BOSSan JuanApril 11 to April 16CA $315
FLLNassauApril 11 to April 17CA $606
MIASanto DomingoApril 12 to April 16CA $616
JFKSan JuanApril 11 to April 16CA $834
JFKSan JuanApril 11 to April 16CA $834
JFKPunta CanaApril 11 to April 13CA $854
JFKSantiago de los CaballerosApril 11 to April 14CA $890
JFKSantiago de los CaballerosApril 11 to April 14CA $890
JFKKingstonApril 11 to April 18CA $981
EWRPunta CanaApril 11 to April 13CA $1,186
LGANassauApril 11 to April 17CA $1,228
JFKNassauApril 11 to April 16CA $1,240
EWRNassauApril 11 to April 16CA $1,698
*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

May 14 - May 21

7 night stay

Montreal (YUL) to Santo Domingo (SDQ)

United • Non-stop • Coach

Santo Domingo (SDQ) to Montreal (YUL)

American Airlines • Non-stop • Coach
per person
found 6 hours ago
Princess Grand Jamaica Resort - All Inclusive
4.5-star property

Princess Grand Jamaica Resort - All Inclusive

May 26 - Jun. 2

7 night stay

Montreal (YUL) to Montego Bay (MBJ)

Air Canada • 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

May 12 - May 19

7 night stay

Montreal (YUL) to Montego Bay (MBJ)

United • Non-stop • Coach

Montego Bay (MBJ) to Montreal (YUL)

American Airlines • Non-stop • Coach
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.
8.6/10 Excellent! (1,001 reviews)
"The history in it and all around it is phenomenal"

Reviewed on Apr. 4, 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 Aquaventure are located nearby.
8.4/10 Very Good! (1,465 reviews)
"Rooms smell bad"

Reviewed on Apr. 8, 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! (867 reviews)
"Excelente"

Reviewed on Apr. 6, 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 Cabbage Beach are located nearby.
8.8/10 Excellent! (1,301 reviews)
"We had a wonderful stay at the Reef Atlantis. It is beautiful here. The hotel, the beach, the pool area were so nice. Everything is convenient and walkable if you want to go to the other hotels and use their pools or the water parks, a shuttle bus takes you to and from each place every 7 minutes ..."

Reviewed on Apr. 6, 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 $157. 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 20 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 April. 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 $157. 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 $157 and CA $1,698 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.