What is the cheapest airline to fly from New Windsor to San Juan round-trip?

Flying on JetBlue is currently your cheapest option to San Juan, with prices starting at $227.

In terms of precipitation, rainfall in San Juan ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit San Juan when rainfall is around 2.2 in.

If weather is an important factor for your trip to San Juan, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

What is the cheapest time of day to fly from SWF to SJU?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Windsor to San Juan as you normally would.

What airport do you fly from for flights from New Windsor to San Juan?

If you book a flight to San Juan from New Windsor, you will be flying from Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor. There are 0 flights from Stewart to San Juan per day from 1 airline.

Can I find deals for flights from Stewart to San Juan that include hotel bookings?

Yes. In addition to deals on Stewart to San Juan flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Stewart to San Juan?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to San Juan.

Can I find deals for business class flights from Stewart to San Juan?

Yes. Cheapflights offers flight deals from Stewart to San Juan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Find Cheap Flights from New Windsor to San Juan

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Find flight deals from Stewart to San Juan

Popular in	July
Cheapest in	October
Average price	$331

Highest demand for flights based on searches. 10% potential increase in price ($41 potential increase over avg. RT price).

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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).

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Average for round-trip flights in September 2026

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Best time to book a flight from Stewart to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan from Stewart with our price prediction graph.

SWF-PR1

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing San Juan

Peruse reviews from past customers who have flown with JetBlue from New Windsor to San Juan to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

JetBlue

7.1

Good

3,043 reviews

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2026

ISP - FLL

Had a four delay with family of 5 was not a great day.

JetBlue

7.1

Good

3,043 reviews

JetBlue

7.1

Good

3,043 reviews

Reviews

1 / 20

6.0

Good

Anonymous,Jul 2026

ISP - FLL

Had a four delay with family of 5 was not a great day.

Related info for your journey

What airport do you fly from for flights from New Windsor to San Juan?
If you book a flight to San Juan from New Windsor, you will be flying from Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor. There are 0 flights from Stewart to San Juan per day from 1 airline.
What is the cheapest airline to fly from New Windsor to San Juan round-trip?
Flying on JetBlue is currently your cheapest option to San Juan, with prices starting at $227.
Can I find deals for flights from Stewart to San Juan that include hotel bookings?
Yes. In addition to deals on Stewart to San Juan flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Stewart to San Juan?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to San Juan.
Can I find deals for business class flights from Stewart to San Juan?
Yes. Cheapflights offers flight deals from Stewart to San Juan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Stewart to San Juan

Top airline flying from Stewart to San Juan

Airline	Cheapest	Average	Flexibility	On-time
JetBlue	Cheapest$227	Average$365	FlexibilityNo cancel fee	On-time62%

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Find cheap flights from Stewart to San Juan with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Stewart to San Juan

Popular in

Cheapest in

Average price

Best time to book a flight from Stewart to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan from Stewart with our price prediction graph.

Reviews of airlines servicing San Juan

Peruse reviews from past customers who have flown with JetBlue from New Windsor to San Juan to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

What airport do you fly from for flights from New Windsor to San Juan?

What is the cheapest airline to fly from New Windsor to San Juan round-trip?

Can I find deals for flights from Stewart to San Juan that include hotel bookings?

How can I find direct flights from Stewart to San Juan?

Can I find deals for business class flights from Stewart to San Juan?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to San Juan

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to San Juan by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Stewart to San Juan by cabin class

Find flights from Stewart to San Juan, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Stewart and San Juan flights

Browse other Stewart and San Juan flight options. Last updated on September 30, 2026.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2026

Top airline flying from Stewart to San Juan

100% Free

Book with Flexibility

Travel Smart

Cheap flights from New Windsor (SWF) to San Juan

Find cheap flights from Stewart to San Juan with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Stewart to San Juan

Popular in

Cheapest in

Average price

Best time to book a flight from Stewart to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan from Stewart with our price prediction graph.

Reviews of airlines servicing San Juan

Peruse reviews from past customers who have flown with JetBlue from New Windsor to San Juan to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

What airport do you fly from for flights from New Windsor to San Juan?

What is the cheapest airline to fly from New Windsor to San Juan round-trip?

Can I find deals for flights from Stewart to San Juan that include hotel bookings?

How can I find direct flights from Stewart to San Juan?

Can I find deals for business class flights from Stewart to San Juan?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to San Juan

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to San Juan by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Stewart to San Juan by cabin class

Find flights from Stewart to San Juan, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Stewart and San Juan flights

Browse other Stewart and San Juan flight options. Last updated on September 30, 2026.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2026

Top airline flying from Stewart to San Juan

100% Free

Book with Flexibility

Travel Smart