Caribbean Flights Are the Cheapest in Years: Here Are the Best Deals

As the winter chill settles in across the country, here’s some travel intel that's likely to be welcome news: Flights to the Caribbean are the cheapest they’ve been in years.

And not just a little cheaper. We’re talking significantly cheaper, according to a new report from Dollar Flight Club.

While it may not necessarily make sense (isn’t everyone trying to fly to warmer locales right now?), it seems dozens of round-trip routes to the sun-drenched Caribbean region are currently priced at just $300, according to Dollar Flight Club’s 2026 Caribbean Flight Report. That includes such hot-spots as Puerto Rico, the U.S. Virgin Islands, Jamaica and the Dominican Republic.

In order to come up with this news, Dollar Flight Club analyzed hundreds of thousands of airfare data points, specifically those covering routes between major U.S. airports and top Caribbean destinations. This analysis included flight data from airline partners, online travel agencies, and major search engines, covering price trends, historical averages, and seasonal fluctuations.

This intensive effort revealed that there are bargains galore available to the Caribbean for the coming few months. Here are some of the stand-out routes on sale right now include:

• Newark Liberty International Airport - San Juan, Puerto Rico: Prices start at $116. Average price: $320. For flights between January and March.
• John F. Kennedy Airport - San Juan, Puerto Rico: Prices start at $136. Average price: $320. For flights between February and April.
• Fort Lauderdale–Hollywood International Airport - San Juan, Puerto Rico: Prices start at $150. Average price: $330. For flights between January and March.
• MCO, Orlando, Florida - U.S. Virgin Islands – St. Thomas: Prices start at $152. Average price: $360. For flights between January and February.
• Philadelphia International Airport - San Juan, Puerto Rico: Prices start at $157. Average price: $350. For flights from February through March.
• Detroit Metropolitan Wayne County Airport - San Juan, Puerto Rico: Prices start at $162. Average price: $370. For flights from January through March.
• Fort Lauderdale–Hollywood International Airport - Aruba: Prices start at $198. Average price: $400. For flights from February through April.
• Fort Lauderdale–Hollywood International Airport - Dominican Republic: Prices start at: $200. Average price: $410. For flights from January through March.
• Fort Lauderdale–Hollywood International Airport - Jamaica, Montego Bay: Prices from $214. Average price: $420. For flights from January through March.

• Newark Liberty International Airport - Grenada: Prices from: $228. Average price: $450. For travel from February through April.

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