Cheap Flights to Caribbean as Low as

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Jet to one of Caribbean's top cities

Malecon

Havana

Flights
Havana
OriginDestinationTravel DatesFlights From*
JFKSan JuanOctober 28 to November 1$198
JFKNassauNovember 28 to January 11$312
JFKSanto DomingoNovember 8 to November 8$320
EWRNassauOctober 17 to October 21$320
JFKSantiago de los CaballerosOctober 6 to October 7$323
JFKPunta CanaDecember 3 to December 8$331
EWRPiarcoOctober 11 to October 25$394
JFKPiarcoNovember 6 to November 10$394
JFKWest EndOctober 15 to November 1$426
JFKWest EndOctober 15 to November 1$426
EWRWest EndDecember 29 to January 4$890
BKKNassauOctober 20 to November 15$1,657
BKKPunta CanaOctober 16 to October 23$1,753
BKKPiarcoNovember 1 to November 29$1,780
BKKSanto DomingoJanuary 4 to January 4$7,808
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MIASan JuanSeptember 30 to October 4$95
EWRSan JuanSeptember 29 to October 3$203
BOSSan JuanOctober 1 to October 3$224
YYZOranjestadSeptember 30 to October 10$317
EWRPunta CanaSeptember 29 to October 7$372
JFKPunta CanaSeptember 29 to October 7$372
YYZMontego BaySeptember 30 to October 3$373
JFKKingstonOctober 1 to October 6$391
YYZPunta CanaSeptember 30 to October 7$394
FLLPiarcoOctober 1 to October 9$398
YYZSan JuanOctober 1 to October 2$435
YYZPiarcoSeptember 30 to October 10$471
JFKWest EndOctober 1 to October 17$506
JFKPiarcoSeptember 30 to October 10$583
MIAOranjestadSeptember 30 to October 2$584
*Prices include taxes and fees

Best Caribbean Flight and Hotel Packages

Fairmont El San Juan Hotel
5.0-star property

Fairmont El San Juan Hotel

Nov 9 - Nov 13

4 night stay

Atlanta (ATL) to San Juan (SJU)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flightPrice was $5,072, price is now $2,880 per person
per person
OLV Hotel - Adults Only
4.0-star property

OLV Hotel - Adults Only

Oct 18 - Oct 21

3 night stay

Atlanta (ATL) to San Juan (SJU)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flightPrice was $1,047, price is now $710 per person
per person
Fairmont El San Juan Villa Experience
5.0-star property

Fairmont El San Juan Villa Experience

Dec 3 - Dec 7

4 night stay

Newark (EWR) to San Juan (SJU)

Spirit Airlines • Non-stop • Coach

San Juan (SJU) to Newark (EWR)

American Airlines • Non-stop • Coach
Save 100% on your flightPrice was $2,120, price is now $1,491 per person
per person
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Prices and availability subject to change. Additional terms may apply.

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, and room service. Our guests praise the pool and the property condition in our reviews. Popular attractions Port of San Juan and Condado Beach are located nearby. Discover genuine guest reviews for Hotel El Convento, in Old San Juan neighborhood, along with the latest prices and availability – book now.
8.6/10 Excellent! (1,003 reviews)
"Excellent"

Reviewed on Sep 21, 2023

Hotel El Convento
Sheraton Old San Juan Hotel

Sheraton Old San Juan Hotel

4 out of 5
100 Brumbaugh Street, San Juan
Stay at this 4-star business-friendly hotel in San Juan. Enjoy free WiFi, breakfast, and room service. Popular attractions Port of San Juan and Condado Beach are located nearby. Discover genuine guest reviews for Sheraton Old San Juan Hotel, in Old San Juan neighborhood, along with the latest prices and availability – book now.
7.8/10 Good! (1,000 reviews)
"They are doing a lot of upgrades, but still was nice. They gave us welcome drink coupon and a food and drink voucher. Great location by the cruise terminal!"

Reviewed on Sep 6, 2023

Sheraton Old San Juan Hotel
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 private beach, and a marina. Our guests praise the pool and the property condition in our reviews. Popular attractions Aquaventure and Paradise Lagoon Beach South are located nearby. Discover genuine guest reviews for The Reef at Atlantis along with the latest prices and availability – book now.
8.6/10 Excellent! (1,001 reviews)
"Beautiful hotel resort. Staff was very helpful and friendly. Room was very spacious for 3. Lots of activities to do or just enjoy the beach."

Reviewed on Sep 14, 2023

The Reef at Atlantis

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Boutique Hotel Palacio

Boutique Hotel Palacio

3.5 out of 5
Calle Duarte 106, Santo Domingo, Distrito Nacional
Stay at this 3.5-star business-friendly hotel in Santo Domingo. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Regional Museum of Archaeology and Calle El Conde are located nearby. Discover genuine guest reviews for Boutique Hotel Palacio, in Zona Colonial neighborhood, along with the latest prices and availability – book now.
8.6/10 Excellent! (1,000 reviews)
"Safety,very good food places to go and eat, quite and the peoples are very nice and friendly. This country is a good place to retire and enjoy yourself"

Reviewed on Sep 18, 2023

Boutique Hotel Palacio
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

Can I fly to Caribbean right now?
There are various factors that could affect your travel plans if you’re thinking about a flight to Caribbean. They include where you’re arriving from and coronavirus restrictions in your destination. Before booking, browse relevant government websites for the latest info. Travelocity’s Covid-19 Travel Advisor will also inform you about traveling during the COVID-19 pandemic. Click on the link to learn about physical distancing rules, quarantine and more for Caribbean.
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 $95. 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.
If I cannot travel due to COVID-19, can I change my booking to a later date?
If COVID-19 has impacted your travel plans, visit our Customer Service Portal link. Whether you need to change your flight or request a refund, you’ll find all the information you need there. For peace of mind, it’s smart to check the terms and conditions of your preferred carrier before booking tickets to Caribbean.
What is the cheapest month to fly to Caribbean?
Spend more money on great adventures rather than airfares by zipping off to Caribbean in October. 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 $95. 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 $95 and $7,808 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.
What can I expect on a flight to Caribbean?
The duration of your flight and whether you’re flying with a full-service or low-priced airline play a major role. If you’re searching for long-haul flights to Caribbean, drinks, food and entertainment will often be included. Want cheap flights for family vacations? You’ll save with budget carriers. These airlines usually don’t have as many inclusions, so be prepared to pay for food and drinks.

Destinations in Caribbean

Top Flight Routes

Top Airlines

Top Airports

*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.