Read also: The Ultimate Guide to Finding Cheap Flights
Methodology
To build the 2026 Caribbean Flight Report, we analyzed hundreds of thousands of airfare data points from major U.S. airports to top Caribbean destinations for travel between January and April 2026. The dataset includes Dollar Flight Club’s proprietary alert data, airline and partner feed data, OTA and fare-search engine pricing, and multi-year historical price curves. By combining real-time fares with long-term patterns, we were able to identify destinations and routes that reliably produce low all-in roundtrip prices rather than isolated flash sales.
We focused on major and mid-sized U.S. gateways that consistently see strong Caribbean deal volume, including EWR, JFK, LGA, BOS, PHL, IAD/DCA, FLL, MIA, MCO, ATL, CLT, IAH/HOU, DFW/DAL, DTW, ORD/MDW, BNA, and others.
The resulting rankings highlight destinations where travelers can expect consistent, accessible low fares throughout the early 2026 winter season.
Top 10 Cheapest City-Pairs (Jan–Apr 2026)
1. EWR → SJU (Puerto Rico – San Juan)
- From $116 (Avg. Price: $320)
- Dates: Jan–Mar
2. JFK → SJU (Puerto Rico – San Juan)
- From $136 (Avg. Price: $340)
- Dates: Feb–Apr
3. FLL → SJU (Puerto Rico – San Juan)
- From $150 (Avg. Price: $330)
- Dates: Jan–Mar
4. MCO → STT (U.S. Virgin Islands – St. Thomas)
- From $152 (Avg. Price: $360)
- Dates: Jan–Feb
5. PHL → SJU (Puerto Rico – San Juan)
- From $157 (Avg. Price: $350)
- Dates: Feb–Mar
6. DTW → SJU (Puerto Rico – San Juan)
- From $162 (Avg. Price: $370)
- Dates: Jan–Mar
7. FLL → AUA (Aruba)
- From $198 (Avg. Price: $400)
- Dates: Feb–Apr
8. FLL → SDQ (Dominican Republic – Santo Domingo)
- From $200 (Avg. Price: $410)
- Dates: Jan–Mar
9. FLL → MBJ (Jamaica – Montego Bay)
- From $214 (Avg. Price: $420)
- Dates: Jan–Mar
10. EWR → GND (Grenada)
- From $228 (Avg. Price: $450)
- Dates: Feb–Apr
Bahamas
Why visit: The Bahamas continues to be one of the easiest and most affordable Caribbean getaways from the U.S. Its mix of short flights, warm weather, and clear waters makes it a go-to for travelers looking for a quick escape without long-haul flights.
Dollar Flight Club insight: We’re seeing roundtrip fares to Nassau (NAS) starting at $240, compared to an average of $460 in early 2025. The best deals depart from Fort Lauderdale and Miami, especially during January and March, when fare competition between budget and legacy carriers peaks.
Puerto Rico
Why visit: Puerto Rico is always in demand, and for good reason. It’s culturally rich, easy to reach, and doesn’t require a passport for U.S. travelers. The island’s mix of culture and nature makes it one of the most versatile Caribbean destinations.
Dollar Flight Club insight: San Juan (SJU) remains one of the most competitive markets in the Caribbean. Fares are as low as $116 roundtrip from Newark, with averages hovering around $330–$360 through March. Routes from Detroit, Philadelphia, and Fort Lauderdale also remain consistently under $200–$220, with budget carriers driving much of the price pressure.
Jamaica
Why visit: Culture-rich, wallet-friendly, and home to some of the Caribbean’s most stunning beaches. Parts of the island were impacted by Hurricane Melissa; please keep recovery efforts in mind as you plan. When Jamaica is ready to welcome visitors again, your trip will directly support local communities.
Dollar Flight Club insight: We’ve tracked roundtrip fares to Montego Bay (MBJ) dipping as low as $214 from Fort Lauderdale, with averages around $400–$420. February shows the strongest availability, and flights from Atlanta and Dallas are pricing 10% lower than last winter.
Dominican Republic
Why visit: With lush rainforests, white-sand beaches, and an incredible mix of all-inclusive resorts, the Dominican Republic remains one of the Caribbean’s best-value islands.
Dollar Flight Club insight: Santo Domingo (SDQ) saw multiple flash price drops in October and November 2025, bringing fares down to $200 roundtrip from Fort Lauderdale. Average prices are holding near $410, still about 12% lower than this time last year. Look for continued dips in late February and early March, especially on Tuesday/Wednesday departures.
Aruba
Why visit: Sunny nearly 365 days a year, Aruba remains a consistent favorite for winter escapes. It’s perfect for travelers who want guaranteed sunshine and calm beaches without worrying about storm season.
Dollar Flight Club insight: Fares to Aruba (AUA) are currently as low as $198 roundtrip from Fort Lauderdale, with averages around $400 through April. Interestingly, shoulder-season pricing (late March–early April) has been 8–10% cheaper than peak February, which could signal strong off-peak value.
Barbados
Why visit: Barbados brings together everything travelers love about the Caribbean at a more accessible price than many expect.
Dollar Flight Club insight: Fares to Bridgetown (BGI) are trending below $280 from East Coast hubs like Newark and Philadelphia, averaging around $430 through March. JetBlue and American have expanded capacity here, which has helped flatten price spikes even during school breaks.
St. Lucia
Why visit: With its dramatic peaks and volcanic beaches, St. Lucia is one of the Caribbean’s most scenic islands. It’s ideal for travelers seeking a mix of relaxation and adventure; think snorkeling by day and sunset views at night.
Dollar Flight Club insight: Flights to St. Lucia (UVF) from New York have dipped to $255 roundtrip, averaging around $420 through March. We’ve also noticed growing availability for midweek departures, which are pricing up to 20% below weekend itineraries.
Grand Cayman
Why visit: Known for its crystal-clear waters and world-class diving, Grand Cayman delivers a high-end feel without always commanding a high-end price tag.
Dollar Flight Club insight: Fares to Grand Cayman (GCM) have hit $205 roundtrip from Fort Lauderdale, averaging around $380 during February and March. Flights from Houston and Dallas are also pricing below $300 this year for the first time in over two years.
When to Book
If you’re planning a Caribbean getaway this winter, your best window to buy is 4–8 weeks before departure, especially for travel between mid-January and mid-March. Tuesday and Wednesday departures with Saturday returns are still 12–25% cheaper than weekend roundtrips. Presidents’ Day week (February 14–21) remains the one stretch where prices consistently spike, so book around it if you can.
Want to plan your 2026 island escape?
Join Dollar Flight Club for free and get instant alerts when flight deals drop up to 90% off from your home airport to destinations across the Caribbean and beyond.
