Skip to content

Caribbean deal alert: Fly to Puerto Rico and US Virgin Islands from $239 round trip

May 13, 2022
6 min read
ocean view in San Juan, Puerto Rico
This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.

There's a killer fare sale happening right now on flights to Caribbean islands that don't require passports (and yes, I did use "killer" as an adjective because I'm a child of the '80s). So if you've been dreaming of blue skies, white sand beaches and drinks with colorful umbrellas, now's the time to book your trip.

American Airlines, Delta Air Lines and United Airlines have marked down fares to evergreen tropical destinations such as the U.S. Virgin Islands — particularly St. Croix and St. Thomas — and San Juan, Puerto Rico. We came across some absolutely epic savings as we searched for itineraries.

The best deals are for fall travel between September and November. However, there are also some sweet bargains on early 2023 winter travel. Remember that basic economy fares with JetBlue and United don't include full-size carry-on bags. It costs between $50 and $80 round trip to upgrade for more overhead bin space. Checked luggage costs around $30 to $35 each way.

Sign up for our daily newsletter

Want more TPG news delivered every morning to your inbox? Sign up for our daily newsletter.

A tip of the travel cap to Scott’s Cheap Flights for alerting travelers of this new deal. Its Premium membership is available for $49 per year. The Elite tier option is available for $199 per year, and it offers access to deals on premium economy, business-class and first-class tickets.

You know what we always say: The more flexible you can be with your travel plans, the better price you'll find.

Deal basics

Airlines: American, Delta, JetBlue, United.
Routes: Atlanta, Chicago, Fort Lauderdale, Los Angeles, Miami, Newark, New York City, Tuscon to San Juan, St. Croix, St. Thomas.
How to book: Search Google Flights and book directly through the airline.
Travel dates: Best availability September-November 2022 and January-March 2023.

Overlooking Charlotte Amalie, Hassel and Water islands from a Blackbeard’s Castle vantage point on St. Thomas in the U.S. Virgin Islands. (Photo by Nick Heinemann/Getty Images)

Related: US Virgin Islands see surge in tourism

Sample flights

Let's start out West, where you can fly from Los Angeles International Airport (LAX) to Luis Muñoz Marín International Airport (SJU) in San Juan in February on American for just $321 round trip. American's basic economy ticket allows for a free carry-on.

(Screenshot from Google Flights)

A nonstop from Hartsfield-Jackson Atlanta International Airport (ATL) to San Juan in January is only $268 on Delta, and this basic economy ticket also comes with a free carry-on.

(Screenshot from Google Flights)

Here's a fantastic fare we found from Chicago's O'Hare International Airport (ORD) to San Juan in late October for only $239 round trip on Delta.

(Screenshot from Google Flights)

Chicago to St. Croix's Henry E. Rohlsen Airport (STX) in late January certainly sounds nice, doesn't it? You can book that itinerary on American for just $357 round trip.

(Screenshot from Google Flights)

Here's an excellent end-of-summer deal for Arizona travelers. You can fly from Tucson International Airport (TUS) to Cyril E. King Airport (STT) on St. Thomas for just $291 round trip through Delta. That's an excellent price for this fare. Please note that the outbound flight includes two stops.

(Screenshot from Google Flights)

If you live in the New York City area, you have plenty of bargain tickets to choose from. JetBlue has Blue Basic fares from JFK to St. Thomas in August for only $274 round trip. That includes a nonstop outbound flight. Carry-on bags are not included, though, so you should consider upgrading a tier for $50, which is cheaper than checking a bag.

(Screenshot from Google Flights)

Nonstop flights from New York City to San Juan in August cost only $276 on JetBlue — a substantial markdown from normal prices. Remember, the Blue Basic fares don't come with a free full-size carry-on, so plan accordingly.

(Screenshot from Google Flights)

If you live in Music City, here's a nice deal for you: You can fly from Nashville International Airport (BNA) to San Juan in January for only $235 round trip on American. We found plenty of availability at this great price in early 2023.

(Screenshot from Google Flights)

Related: Cleared for takeoff: A trip to Puerto Rico for a family of four

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.

TPG featured card

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

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

$95

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