6 Cheap Caribbean Flights Under $400 To Book Now for a Winter Escape
Written by
Gabrielle Olya
Edited by
Molly Sullivan
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If you’re dreaming of warm weather and turquoise waters while shoveling snow, you don’t need a big budget to make it happen. Dollar Flight Club analyzed thousands of airfare data points from major U.S. airports to top Caribbean destinations for travel between January and April 2026 to find the cheapest flight routes — perfect for a winter escape.
Based on this analysis, here’s where you can fly for less than $400 on average.
1. Newark, New Jersey (EWR) to San Juan, Puerto Rico (SJU)
- Cheapest flights: From $116
- Average price: $320
- Dates: January-March
2. Queens, New York (JFK) to San Juan, Puerto Rico (SJU)
- Cheapest flights: From $136
- Average price: $340
- Dates: February-April
3. Fort Lauderdale, Florida (FLL) to San Juan, Puerto Rico (SJU)
- Cheapest flights: From $150
- Average price: $330
- Dates: January-March
4. Orlando, Florida (MCO) to St. Thomas, US Virgin Islands (STT)
- Cheapest flights: From $152
- Average price: $360
- Dates: January-February
5. Philadelphia (PHL) to San Juan, Puerto Rico (SJU)
- Cheapest flights: From $157
- Average price: $350
- Dates: February-March
6. Detroit (DTW) to San Juan, Puerto Rico (SJU)
- Cheapest flights: From $162
- Average price: $370
- Dates: January-March
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