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Deal Alert: NYC and Chicago to San Juan From $198 Round-Trip

Sept. 20, 2016
3 min read
san juan - featured
Deal Alert: NYC and Chicago to San Juan From $198 Round-Trip
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Airfare deals are typically only available on limited dates. We recommend that you use Google Flights to find dates to fly, then book through an online travel agency, such as Orbitz, which allows you to cancel flights without penalty by 11pm Eastern Time within one day of booking. Remember: Fares may disappear quickly, so book right away and take advantage of Orbitz's courtesy cancellation if you're unable to travel. Additionally, keep in mind that discounted partner fares may not earn miles with US-based carriers.

As the Northeast starts to cool down, many will be looking to escape the cold. These cheap fares to San Juan, Puerto Rico are a great way to do just that. JetBlue has tickets starting at just $198 round-trip from New York City (JFK) and Chicago (ORD) to San Juan (SJU). We're seeing wide availability from the end of September through January 2017 .

Although parts of Miami have recently been declared Zika-free, there is still a CDC travel warning to Puerto Rico due to the virus' outbreak there. Make sure you know how to protect yourself from the Zika if traveling to the island.

Airline: JetBlue
Route: JFK and ORD to SJU
Cost: $198+ round-trip in Economy
Dates: September 2016 - January 2017
Booking Link: Expedia
Pay With: Chase Sapphire Reserve, Premier Rewards Gold Card from American Express, Citi Prestige Card or Chase Sapphire Preferred

Here are a few examples of what you can book:

New York (JFK) to San Juan (SJU) for $198 round-trip in October:

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New York (JFK) to San Juan (SJU) for $198 round-trip in October.

Chicago (ORD) to San Juan (SJU) for $198 round-trip in November:

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Chicago (ORD) to San Juan (SJU) for $198 round-trip in November.

Maximize Your Purchase

Don't forget to use a credit card that earns additional points on airfare purchases, such as the Chase Sapphire Reserve, American Express Premier Rewards Gold or Citi Prestige (3x on airfare) or the Chase Sapphire Preferred Card (2x on all travel purchases). Check out this post for more on maximizing airfare purchases.

H/T: The Flight Deal

If you're able to score one of these tickets, please share the good news in the comments below!