Deal alert: Flights to Puerto Rico and Cuba from $125 round-trip

Jan 30, 2020

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Flights to island destinations such as Puerto Rico and Cuba are currently available from $125 round-trip.

One of the most shocking flight deals is the round-trip, nonstop fare from Newark (EWR) to San Juan (SJU) for just $125 round-trip.

Yes, it’s in United’s basic economy but all you need to pack is a suit and some flip flops, so who needs a carry-on anyway?

If you’re interested in taking advantage of one of the low-cost Cuba fares, make sure you read this first as there’s a bit of a caveat for American tourists.

To search, head to Google Flights and enter your origin and destination cities. Scroll through the calendar function to find dates and prices that work for you. Finally, click through to book directly with the airline or through an OTA like Priceline or Expedia.

Airlines: United, Delta, American, JetBlue
Routes: EWR/MCO/BOS/MIA/CLE/ORD/DTW/LAX to SJU/HAV
Cost: $125+ round-trip in basic economy
Travel Dates: 
February – May 2020
Pay With:
The Platinum Card® from American Express (5x on airfare booked directly with the airline), Citi Prestige® Card (5x on airfare),  Citi Premier® Card (3x on airfare), Chase Sapphire Reserve (3x on travel), American Express® Gold Card (3x on airfare booked directly with the airline or amextravel.com) or Chase Sapphire Preferred Card (2x on travel)

The information for the Citi Prestige has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Here’s an example of what you can book:

Newark (EWR) to San Juan (SJU) for $125 round-trip on United:

Orlando (MCO) to San Juan (SJU) for $178 round-trip on JetBlue:

Boston (BOS) to San Juan (SJU) for $198 round-trip on JetBlue:

Miami (MIA) to Havana (HAV) for $205 round-trip on Delta:

Cleveland (CLE) to San Juan (SJU) for $236 round-trip on American:

Chicago (ORD) to San Juan (SJU) for $244 round-trip on JetBlue:

Detroit (DTW) to San Juan (SJU) for $270 round-trip on Delta:

Los Angeles (LAX) to Havana (HAV) for $283 round-trip on American:

Maximize your purchase

Don’t forget to use a credit card that earns additional points on airfare purchases, such as The Platinum Card® from American Express (5x on flights booked directly with airlines or American Express Travel), Citi Prestige® Card (5x on airfare), Chase Sapphire ReserveAmerican Express® Gold Card Citi Premier® Card (3x on airfare) or the Chase Sapphire Preferred Card (2x on all travel purchases). Check out this post for more on maximizing airfare purchases.

Featured photo by Liz Hund/The Points Guy.

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