HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$122+ Cheap flights from Jacksonville to New Windsor (JAX - SWF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SWF
Mar 2 — Mar 91
Mon 3/2
Mon 3/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Jacksonville to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Jacksonville to Stewart

Cheapest flights from Jacksonville to Stewart
Explore the most affordable flight options available from Jacksonville to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 31, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:03 pm
JAX
-
SWF
1 stop14h 22m
Breeze Airways
Sat 5/2312:05 pm
SWF
-
JAX
1 stop20h 33m
Breeze Airways
Deal found 1/28$292
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:03 pm
JAX
-
SWF
1 stop14h 22m
Multiple Airlines
Fri 6/55:55 pm
SWF
-
JAX
2 stops14h 53m
Multiple Airlines
Deal found 1/30$387
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:03 pm
JAX
-
SWF
1 stop14h 22m
Multiple Airlines
Fri 5/295:53 pm
SWF
-
JAX
2 stops14h 55m
Multiple Airlines
Deal found 1/29$411
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/239:03 pm
JAX
-
SWF
1 stop14h 22m
Multiple Airlines
Mon 6/295:55 pm
SWF
-
JAX
2 stops21h 33m
Multiple Airlines
Deal found 1/29$468
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:03 pm
JAX
-
SWF
1 stop14h 22m
Multiple Airlines
Fri 7/105:49 pm
SWF
-
JAX
2 stops14h 59m
Multiple Airlines
Deal found 1/30$503
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/239:03 pm
JAX
-
SWF
1 stop14h 22m
Multiple Airlines
Fri 6/265:55 pm
SWF
-
JAX
2 stops14h 53m
Multiple Airlines
Deal found 1/31$591

Find flight deals from Jacksonville to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (JAX) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

February

Average price

$207
Provider with most accurate pricing for Jacksonville-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jacksonville-New Windsor Stewart flights.
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jacksonville to Stewart that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 31, 2026.
Use the filters below to find and compare flights from Jacksonville to New Windsor that are best for you.

Fly from

Jacksonville

Fly to

Stewart

Route

Depart

Return

Price

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Tue 5/19

9:03 pm-11:25 am

1 stop14h 22m

New Windsor Stewart

Sat 5/23

12:05 pm-8:38 am

1 stop20h 33m

$292

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Tue 6/2

9:03 pm-11:25 am

1 stop14h 22m

New Windsor Stewart

Fri 6/5

5:55 pm-8:48 am

2 stops14h 53m

$387

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Tue 5/26

9:03 pm-11:25 am

1 stop14h 22m

New Windsor Stewart

Fri 5/29

5:53 pm-8:48 am

2 stops14h 55m

$411

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Tue 6/23

9:03 pm-11:25 am

1 stop14h 22m

New Windsor Stewart

Mon 6/29

5:55 pm-3:28 pm

2 stops21h 33m

$468

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Tue 7/7

9:03 pm-11:25 am

1 stop14h 22m

New Windsor Stewart

Fri 7/10

5:49 pm-8:48 am

2 stops14h 59m

$503

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 6/5

9:46 pm-9:38 am

2 stops35h 52m

New Windsor Stewart

Sat 6/13

12:05 pm-8:38 am

1 stop20h 33m

$513

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Tue 6/23

9:03 pm-11:25 am

1 stop14h 22m

New Windsor Stewart

Fri 6/26

5:55 pm-8:48 am

2 stops14h 53m

$591

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Wed 3/4

7:53 pm-9:19 am

2 stops13h 26m

$122

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Wed 2/11

7:53 pm-10:52 am

2 stops14h 59m

$134

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sat 2/28

7:56 pm-11:02 am

2 stops15h 06m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 14 results
1
2

Compare providers for flights from Jacksonville to Stewart

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Jacksonville to Stewart in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Jacksonville-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jacksonville-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jacksonville-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Jacksonville-New Windsor flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Jacksonville-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Jacksonville to Stewart

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

Cheapflights Insights

Everything you need to know about your flight from Jacksonville to New Windsor

What is the cheapest month to book a flight from Jacksonville to New Windsor?

Currently, December is the cheapest month in which you can book a flight from Jacksonville to New Windsor (average of $65). Flying from Jacksonville to New Windsor in July is currently the most expensive (average of $128). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Jacksonville to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Jacksonville to New Windsor?

    Breeze Airways can get you from Jacksonville to New Windsor in just under 14h 22m. Your travel time can differ by up to . The distance from Jacksonville to New Windsor is about 869 mi.

  • Can I find deals for flights from Jacksonville to Stewart that include hotel bookings?

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

  • How can I find direct flights from Jacksonville to Stewart?

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

  • Can I find deals for business class flights from Jacksonville to Stewart?

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

  • What is the cheapest month to book a flight from Jacksonville to New Windsor?

    Currently, December is the cheapest month in which you can book a flight from Jacksonville to New Windsor (average of $65). Flying from Jacksonville to New Windsor in July is currently the most expensive (average of $128). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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 Jacksonville to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to John F Kennedy Intl flights
Miami to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
Miami to LaGuardia flights
Fort Lauderdale to Newark flights
Fort Lauderdale to LaGuardia flights
Miami to Newark flights
Orlando to LaGuardia flights
Orlando to Newark flights
Tampa to John F Kennedy Intl flights
West Palm Beach to Newark flights
Tampa to LaGuardia flights
Tampa to Newark flights
West Palm Beach to John F Kennedy Intl flights
West Palm Beach to LaGuardia flights
Jacksonville to John F Kennedy Intl flights
Jacksonville to Newark flights
Jacksonville to LaGuardia flights
Fort Myers to John F Kennedy Intl flights
Fort Myers to Newark flights
Sarasota to John F Kennedy Intl flights
Orlando to White Plains flights
Pensacola to LaGuardia flights
Fort Myers to LaGuardia flights
Sarasota to Newark flights
Orlando to Buffalo flights
Pensacola to John F Kennedy Intl flights
Pensacola to Newark flights
Sarasota to LaGuardia flights
Orlando to Stewart flights
Tampa to Islip flights
Tampa to Buffalo flights
Orlando to Syracuse flights
Orlando to Islip flights
West Palm Beach to Islip flights
Tampa to White Plains flights
Orlando to Albany flights
Fort Lauderdale to White Plains flights
Fort Myers to White Plains flights
West Palm Beach to White Plains flights
Orlando to Rochester flights
Tallahassee to John F Kennedy Intl flights
Gainesville to John F Kennedy Intl flights
Gainesville to Newark flights
Fort Lauderdale to Stewart flights
Fort Lauderdale to Buffalo flights
Tallahassee to Newark flights
Fort Lauderdale to Islip flights
Panama City to LaGuardia flights
Daytona Beach to John F Kennedy Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.