A new report from Dollar Flight Club found flights to the Caribbean this winter are cheaper than they’ve been in years. The report looked at airfare between major U.S. airports and Caribbean destinations, for travel between January and April 2026, contrasting those fares against long-term patterns.
One of the standout destinations? San Juan, Puerto Rico. Right now, travelers can head to San Juan from multiple major U.S. hubs, including Newark (EWR), New York City (JFK), Fort Lauderdale (FLL), Philadelphia (PHL) and Detroit (DTW) at fares averaging around $300–350, though flights start as low as $116.
Other destinations proving budget-friendly this winter? Flights to Nassau are starting at around $240, compared to the $460 average from last year around this time. Similar fare differences can be seen in flights to Jamaica, the Dominican Republic, Aruba, Barbados and St. Lucia.
Dollar Flight Club advises, if you are going to take advantage of some of these seasonal deals, to attempt to book your flight four–eight weeks out. Additionally, the brand noted travelers can see significant savings by booking a Tuesday or Wednesday departure with a Saturday return, as opposed to a weekend roundtrip.
Read This Next
#TrazeeTravel
Insta FeedDestinations / North America
Jun 15, 2026Experience Astrotourism in This New Mexico Destination
Taos, New Mexico, invites travelers to experience its dark side. The city in northern New Mexico is known for its art and cultural attractions, with its stargazing opportunities becoming increasingly popular.
Sponsored Content
A New Rhythm of Work in Seoul
SEOUL REDEFINES THE FUTURE OF WORKATION by seamlessly integrating business, leisure and culture across the city. From the established MICE hub of Magok to the creative energy and scenic lifestyle along the Han River, it offers a dynamic ecosystem where productivity and relaxation naturally coexist — positioning Seoul as a global destination for a new way of working and living.
Hotel
Jun 15, 2026Anantara Plans to Open First Property in Caribbean
Minor Hotels’ luxury Anantara brand is bringing its first property to the Caribbean. Anantara Turks and Caicos Resort & Residences is expected to open in 2029.
Hotel
Jun 15, 2026Third citizenM Hotel in Washington, D.C., to Debut in Georgetown District
This month, citizenM opens its third Washington, D.C., property, citizenM Washington, D.C. Georgetown. The opening marks the first property opening for citizenM as part of Marriott Bonvoy, meaning all citizenM guests can now earn and redeem Marriott Bonvoy points across all citizenM stays.
Sponsored Content
An Adults-Only Resort for All the Milestone Moments
On Saturday, Feb.14, Devossion by Live Aqua celebrated its grand opening, marking a significant milestone for Grupo Posadas and the Live Aqua brand. This adults-only resort focuses on celebration, authentic Mexican experiences and elevated hospitality — perfectly situated in the heart of the Riviera Maya.
Hotel
Jun 12, 2026Kimpton Ashbel New York-Park Avenue Launches Package for Pet Owners
Kimpton Ashbel New York-Park Avenue, in the heart of Midtown Manhattan, is a new hotel known for stylish accommodations and proximity to Grand Central Terminal, Bryant Park, Fifth Avenue shopping and plenty of other iconic New York City cultural attractions. The design-forward property with townhouse-inspired interiors provides the perfect home base for travelers looking to explore New York City with pets.
ShareThis