Hand-picked deals by our pirate team
Get inspired!
Hand-picked deals by our pirate team
Hand-picked deals by our pirate team
Get inspired!
Hand-picked deals by our pirate team
Our Roundup of The Cheapest Flights to the Caribbean! ✈️ 🌴
Flights to Puerto Rico, Bahamas, Barbados & More from $65 One-Way — JetBlue, American & United
From $65
Pirates, there’s always time for a beach getaway, and the Caribbean’s stunning beaches are calling! We’ve rounded up the best flight deals to some of our favorite tropical destinations, starting from $65 one-way.
Explore Puerto Rico, Turks & Caicos, Aruba, and more, with flights on JetBlue, American, and United.
Departure
- New York City
- Boston
- Los Angeles
- Miami
- Orlando
- Raleigh
- Nashville
- Pittsburgh
Destination
- San Juan
- Nassau
- Aruba
- Turks and Caicos Islands
- Barbados
- Punta Cana
- Cayman Islands
Details
We found some dates and departure airports for you, but more are available.
Click on the links below to change your departure city and date.
Example of Cheapest Flight
Additional Information
All of our deals are available at the time of publishing, but prices are subject to fluctuations and changes at any time.
Download Our App
The easiest way to see all our content first.
Tags
Report a legal concernWe value your privacy
We use cookies to enhance your browsing experience, serve personalized content, and analyze our traffic. By clicking "Accept All" you accept this and consent that we share this information with third parties and that your data may be processed in the USA. For more information, please read our .
You can adjust your preferences at any time. If you deny, we will use only the essential cookies and unfortunately, you will not receive any personalized content. To deny, .