Deal alert: Late summer and fall trips to Puerto Rico for $250 or less

Jun 27, 2022

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Here’s an option for travelers looking to get one more trip on the calendar before we move too far past summer, or to plan what will undoubtedly be a much-needed fall getaway. If you’re willing to travel just after the peak summer travel period unofficially ends, you can get some pretty great deals on flights to Puerto Rico. A popular destination for its resorts and beaches, among other things, you can find flights to San Juan for $250 and under starting around Labor Day weekend and lasting well into fall.

If you haven’t flown on an ultra-low-cost airline before, we’ll go over what you’ll pay in fees if you choose one of the lower fares on Spirit. There are also some deals available on the legacy carriers, but you may have to look around a bit more to find them.

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Whether you’ve held off on booking flights for the summer because the airfare hasn’t been right or you’re looking for an excuse to travel to a Caribbean destination, this could be something to consider.

Scott’s Cheap Flights was the first to point out the great fares to San Juan. The site offers memberships starting at $49 for economy deals, and $149 for a premium membership that will alert you to great business- and first-class fares.

(Photo by HaizhanZheng/Getty Images)

Related: 8 reasons to visit Puerto Rico right now

Deal Basics

Airlines: American, Delta, United and Spirit.
Routes: Newark, Baltimore, Chicago, Atlanta, Miami, Philadelphia and other eastern U.S. cities to San Juan.
Travel dates: September-October.
How to book: Directly with the airlines or with Google Flights.

The vast majority of the deals we found available in the late summer and fall months were aboard low-cost carrier Spirit Airlines and they’re pretty widespread. If you live in the eastern U.S. and Spirit serves your home airport, there’s a good chance you can find a round trip to San Juan for $250 or less.

Now, one of the things you want to always keep in mind — with any airline, but particularly low-cost carriers — is what the fees will entail; the fare is very much only one part of your ultimate trip cost.

For instance, when I go to Spirit’s website to book a round trip to Luis Muñoz Marín International Airport (SJU) out of Newark Liberty International Airport (EWR) I can select a round-trip fare of $164 in Spirit’s most discounted fare class. My ticket doesn’t include a full-size carry-on though, and certainly not a checked bag.

spirit fees screenshot
(Screenshot from Spirit Airlines)

If you’re a light packer planning to just go to Puerto Rico for the weekend with a few items in a backpack you can fit under the seat, you’re in luck. However, to bring a full-size carry-on bag, you’ll have to pay an extra $59 for this trip each way — $118 round-trip. That upgrade also gets you a checked bag and the right to pick your seat and board earlier.

Not interested in flying on a low-cost airline? If you can be flexible with your travel dates, you may be able to track down a comparable deal on one of the legacy airlines.

Here are a few of the routes and prices we found:

  • Baltimore to San Juan for $253 on Delta.
  • Chicago to San Juan for $259 on United.
  • Newark to San Juan for $260 on JetBlue.
  • Boston to San Juan for $239 (base fare) on Spirit.
  • Fort Lauderdale to San Juan for $176 (base fare) on Spirit.
  • Miami to San Juan for $118 (base fare) on Spirit.

We’ll start by taking a look at one of the Spirit itineraries. Departing from Miami International Airport (MIA) just after Labor Day weekend, it’s a quick 2 1/2 hours or so to San Juan (SJU) aboard Spirit. Google Flights notes that for this particular itinerary, you’d pay $78 for the round trip to check a bag, bringing your cost (with no seat selection) to $196 for the trip.

spirit booking screenshot
(Screenshot from Google Flights)

While there are numerous options aboard Spirit out of the New York area, I also found a September option on JetBlue for $260 round-trip out of Newark. You get nonstop service on the southbound trip with a stop in Boston on the way home.

jetblue booking screenshot
(Screenshot from Google Flights)

Washington, D.C.-area travelers can get to Puerto Rico and back out of Baltimore/Washington Thurgood Marshall International Airport (BWI) for $253 aboard Delta. The trip involves a stop in both directions at New York’s John F. Kennedy International Airport (JFK).

delta booking screenshot
(Screenshot from Google Flights)

United loyalists departing from Chicago can get a $259 round-trip fare out of O’Hare International Airport (ORD). The layover on the outbound trip is a little longer than I’d prefer — north of four hours, but not terrible — at Houston’s George Bush Intercontinental Airport (IAH) with a much shorter stop on the return trip at Washington’s Dulles International Airport (IAD).

united booking screenshot
(Screenshot from Google Flights)

Regardless of the airline or itinerary, it is worth noting that this deal does fall during portions of peak Atlantic hurricane season. For that reason, it could be worth considering some sort of travel insurance or flexible ticket just to protect yourself in the event Mother Nature does not cooperate with your travel plans.

Related: Your points and miles guide to Puerto Rico

Maximize your purchase

Pay with: The Platinum Card® from American Express earns you 5 points per dollar when you book directly through the airline or through American Express Travel (on up to $500,000 on these purchases per calendar year). The Chase Sapphire Preferred Card earns you 5 points per dollar on travel purchased through Chase Ultimate Rewards. If you’re a frequent Spirit Airlines traveler booking this deal, you might consider buying your ticket with the Free Spirit® Travel More World Elite Mastercard®, which gets you 3 points per dollar on eligible Spirit purchases.

Condado Beach in San Juan, Puerto Rico. (Photo by Clint Henderson/The Points Guy)

Bottom line

This deal presents a great opportunity to avoid the largest summer crowds by booking a trip just after peak travel season in early to mid-September, or to escape to warm weather in Puerto Rico just as some parts of the U.S. are beginning to experience some chillier fall temperatures.

Featured photo by gregobagel/Getty Images.

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