Want to escape the winter chill without going over budget? It’s easier than you might think, especially if you want cheap flights to Puerto Rico and other Caribbean destinations.
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All you need is a reliable booking platform, a list of eligible islands, and round-trip flights for under $300.
I know—it sounds too good to be true, but it does come with a little catch. You need to be pretty laser-focused when it comes to finding the right deals. Not all airports let you book cheap flights, meaning you might need to factor in connecting flights to your total costs.
That being said, Dollar Flight Club and CheapOair make it easy to find great deals in January and February for cheap flights to Puerto Rico, Mexico, the Dominican Republic, and beyond. These are the best deals out there, broken down by platform.
(Just a note: You need to become a member to take advantage of deals on Dollar Flight Club. You can start a trial for free, but be mindful of when the free trial ends and what your options are to cancel it, in case it doesn’t work out.)
Cheap flights to Puerto Rico & the Caribbean
Offers from CheapOair for January and February
Atlanta to San Juan, Puerto Rico
- January 20–27
- Starting at $217.99 on Spirit
Newark to Santo Domingo, Dominican Republic
- February 3–10
- Starting at $327.99 on Spirit
New York City to Punta Cana, Dominican Republic
- February 3–10
- Starting at $355.54 on American
Offers from Dollar Flight Club for January – April
New York City (EWR) to San Juan, Puerto Rico
- January – March
- Starting at $116 (Avg. Price: $320)
New York City (JFK) to San Juan, Puerto Rico
- February – April
- Starting at $136
Orlando to St. Thomas, US Virgin Islands
- January – February
- Starting at $152
Philadelphia to San Juan, Puerto Rico
- February – March
- Starting at $157
Dallas to San Juan, Puerto Rico
- January – March
- Starting at $162
Fort Lauderdale to Aruba
- February – April
- Starting at $198
Fort Lauderdale to Santo Domingo, Dominican Republic
- February – March
- Starting at $200
Fort Lauderdale to Montego Bay, Jamaica
- January – March
- Starting at $214
New York City (Newark) to Grenada
- February – April
- Starting at $228
