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Deal alert: Winter fares to Puerto Rico from various US cities for under $300 round trip

June 20, 2022
5 min read
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A winter escape to the sunnier climes is a cherished tradition. Savvy travelers know to plan these trips well in advance, especially this year since deals are harder to come by.

Right now, there are quality discount airfares to Puerto Rico, with several sub-$300 round-trip tickets available. San Juan is a particularly attractive destination for those who live in cities that are often frigid in winter, such as Buffalo, Chicago, Cleveland, New York City and Washington, D.C., all of which are part of this sale. That's even more true now that all COVID-19 travel restrictions have been removed for visitors.

This fare sale is for economy tickets, so expect to pay at least $60 to check a bag if you need to do so. The majority of the sale fares we found were for travel between September and March 2023.

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Thanks to Scott’s Cheap Flights for first alerting us to this deal. Its Premium membership is available for $49 per year, while the Elite tier option is available for $199 per year. The latter offers access to deals on premium economy, business- and first-class tickets. As always, try to be as flexible with your travel plans as possible, as it'll typically help you find better prices.

Deal basics

Airlines: American, Delta, JetBlue.
Routes: Akron, Ohio; Baltimore; Chicago; Cleveland; Newark; New York City; Washington, D.C.; and more to San Juan, Puerto Rico.
How to book: Search Google Flights and book directly through the airline.
Travel dates: From September through March 2023.

(Photo by Wyatt Smith/The Points Guy)

Sample flights

Once football season ends and the winter weather really kicks in in cities like Buffalo, a trip south may be just what you need. Consider heading to sunny San Juan, where average daytime highs rarely fall below 85 degrees year-round. Delta has round-trip fares from Buffalo Niagara International Airport (BUF) for just $305, a nice markdown from regular prices.

(Screenshot from Google Flights)

You can fly American out of Cleveland Hopkins International Airport (CLE) to Puerto Rico in March for only $297 round trip. It's a basic economy fare, so keep in mind that you only get a free carry-on bag. If you wish to check a bag, it will cost you $60.

(Screenshot from Google Flights)

You can fly Delta out of Chicago's O'Hare International Airport (ORD) to Puerto Rico in January and February for as low as $309 round trip. We found lots of availability at this price in early 2023.

(Screenshot from Google Flights)

Indianapolis International Airport (IND) to Puerto Rico is also available in January for just $261 round trip on American.

(Screenshot from Google Flights)

Additionally, you can fly nonstop on JetBlue out of New York City's John F. Kennedy International Airport (JFK) to San Juan for only $296 in early December. That's a great price for this route during the holiday travel season, and we saw quite a bit of availability at this price.

(Screenshot from Google Flights)

JetBlue has excellent fares out of Washington, D.C.'s Ronald Reagan Washington National Airport (DCA) to San Juan just before Christmas, too. You can fly nonstop for only $304, a huge savings from what this route normally costs during the holiday season.

(Screenshot from Google Flights)

Maximize your purchase

Pay with: The Platinum Card® from American Express for 5 points per dollar on airfare booked directly with the airline or through American Express Travel (on up to $500,000 on these purchases per calendar year), the Citi Prestige® Card for 5 points per dollar on airfare, the Citi Premier® Card or Chase Sapphire Reserve for 3 points per dollar on air travel, the American Express® Gold Card for 3 points per dollar on airfare when booked directly with the airline or through Amex Travel, or the Chase Sapphire Preferred Card for 2 points per dollar on travel.

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

Featured image by Getty Images/iStockphoto
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
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Rewards

1 - 3X points
3XEarn 3 Points per $1 spent at Restaurants and Supermarkets
3XEarn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
1XEarn 1 Point per $1 spent on all other purchases

Intro offer

Earn 80,000 ThankYou® points60,000 points
For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening

Annual Fee

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Recommended Credit

670-850
Excellent, Good
Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

Why We Chose It

The Citi Premier’s 3 points per dollar spent across a wide range of popular categories is one of the more lucrative offerings in the world of points and miles. The Citi Premier comes with a $95 annual fee and is currently offering a solid sign up bonus of 80,000 points after you spend $4,000 on purchases within the first three months. It also has some valuable transfer partners to make the most of your rewards. Add in access to Citi Entertainment plus a $100 hotel credit for any single-stay hotel booking that exceeds $500 or more, excluding taxes and fees, booked through the Citi travel website, there are few reasons why the Citi Premier should not be in every traveler’s wallet.

Pros

  • Earns 3x points on restaurants, supermarkets, gas stations, air travel and hotels.
  • $100 annual hotel savings benefit (on single hotel stay bookings of $500 or more, excluding taxes and fees, booked through thankyou.com)
  • Points transfer to 16 airline programs, from JetBlue to Virgin Atlantic.
  • World Elite Mastercard benefits, extended warranty, damage and theft protection.

Cons

  • $95 annual fee
  • Lacks travel protections that other travel rewards cards come with
  • For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening
  • Earn 3 Points per $1 spent at Restaurants and Supermarkets
  • Earn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
  • Earn 1 Point per $1 spent on all other purchases
  • Annual Hotel Savings Benefit
  • 80,000 Points are redeemable for $800 in gift cards when redeemed at thankyou.com
  • No expiration and no limit to the amount of points you can earn with this card
  • No Foreign Transaction Fees on purchases
Best starter travel card
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards Rate

3XEarn 3 Points per $1 spent at Restaurants and Supermarkets
3XEarn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
1XEarn 1 Point per $1 spent on all other purchases
  • Intro Offer
    For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening

    Earn 80,000 ThankYou® points
    60,000 points
  • Annual Fee

    $95
  • Recommended Credit
    Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

    670-850
    Excellent, Good

Why We Chose It

The Citi Premier’s 3 points per dollar spent across a wide range of popular categories is one of the more lucrative offerings in the world of points and miles. The Citi Premier comes with a $95 annual fee and is currently offering a solid sign up bonus of 80,000 points after you spend $4,000 on purchases within the first three months. It also has some valuable transfer partners to make the most of your rewards. Add in access to Citi Entertainment plus a $100 hotel credit for any single-stay hotel booking that exceeds $500 or more, excluding taxes and fees, booked through the Citi travel website, there are few reasons why the Citi Premier should not be in every traveler’s wallet.

Pros

  • Earns 3x points on restaurants, supermarkets, gas stations, air travel and hotels.
  • $100 annual hotel savings benefit (on single hotel stay bookings of $500 or more, excluding taxes and fees, booked through thankyou.com)
  • Points transfer to 16 airline programs, from JetBlue to Virgin Atlantic.
  • World Elite Mastercard benefits, extended warranty, damage and theft protection.

Cons

  • $95 annual fee
  • Lacks travel protections that other travel rewards cards come with
  • For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening
  • Earn 3 Points per $1 spent at Restaurants and Supermarkets
  • Earn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
  • Earn 1 Point per $1 spent on all other purchases
  • Annual Hotel Savings Benefit
  • 80,000 Points are redeemable for $800 in gift cards when redeemed at thankyou.com
  • No expiration and no limit to the amount of points you can earn with this card
  • No Foreign Transaction Fees on purchases