HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$136+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SWF
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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

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 September 15, 2025.

Round-trip from

$378
(Mytrip)

One-way from

$136
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$222
From Jacksonville to New Windsor Stewart
Search Deals
One-way flight from Jacksonville to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find 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 September 15, 2025.

This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/28:44 amJAX - SWF
2 stops26h 37mMultiple Airlines
Sun 10/57:11 pmSWF - JAX
2 stops25h 25mMultiple Airlines
Deal found 9/15$378
This Mytrip deal was found by Cheapflights users on 9/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:44 amJAX - SWF
3 stops24h 57mMultiple Airlines
Thu 11/66:14 pmSWF - JAX
2 stops26h 22mMultiple Airlines
Deal found 9/14$379
This Mytrip deal was found by Cheapflights users on 9/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/23:26 pmJAX - SWF
2 stops19h 55mAllegiant Air
Sun 10/57:11 pmSWF - JAX
2 stops25h 25mAllegiant Air
Deal found 9/13$393
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/233:26 pmJAX - SWF
2 stops19h 15mAllegiant Air
Sun 10/267:11 pmSWF - JAX
2 stops22h 32mAllegiant Air
Deal found 9/15$406
This Mytrip deal was found by Cheapflights users on 9/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/163:26 pmJAX - SWF
2 stops19h 15mAllegiant Air
Sun 10/197:11 pmSWF - JAX
2 stops25h 25mAllegiant Air
Deal found 9/12$414
This Mytrip deal was found by Cheapflights users on 9/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/123:26 pmJAX - SWF
2 stops18h 45mAllegiant Air
Sun 10/197:11 pmSWF - JAX
2 stops25h 25mAllegiant Air
Deal found 9/14$529
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/257:37 pmJAX - SWF
2 stops22h 58mAllegiant Air
Sun 11/3012:51 pmSWF - JAX
2 stops20h 54mAllegiant Air
Deal found 9/15$879
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/202:25 pmJAX - SWF
2 stops21h 19mBreeze Airways
Mon 11/2412:24 pmSWF - JAX
2 stops29h 54mBreeze Airways
Deal found 9/14$908

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 September 15, 2025.
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

Thu 10/30

9:44 am-10:41 am

3 stops24h 57m

New Windsor Stewart

Thu 11/6

6:14 pm-8:36 pm

2 stops26h 22m

$378

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 10/2

8:44 am-11:21 am

2 stops26h 37m

New Windsor Stewart

Sun 10/5

7:11 pm-8:36 pm

2 stops25h 25m

$378

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 10/2

3:26 pm-11:21 am

2 stops19h 55m

New Windsor Stewart

Sun 10/5

7:11 pm-8:36 pm

2 stops25h 25m

$393

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 10/23

3:26 pm-10:41 am

2 stops19h 15m

New Windsor Stewart

Sun 10/26

7:11 pm-5:43 pm

2 stops22h 32m

$406

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 10/16

3:26 pm-10:41 am

2 stops19h 15m

New Windsor Stewart

Sun 10/19

7:11 pm-8:36 pm

2 stops25h 25m

$414

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sun 10/12

3:26 pm-10:11 am

2 stops18h 45m

New Windsor Stewart

Sun 10/19

7:11 pm-8:36 pm

2 stops25h 25m

$539

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 1/22

2:21 pm-11:31 am

2 stops21h 10m

New Windsor Stewart

Mon 1/26

12:11 pm-5:08 pm

2 stops28h 57m

$722

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sun 10/5

12:38 pm-10:26 am

2 stops45h 48m

$136

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 10/16

6:03 pm-10:41 am

2 stops16h 38m

$150

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 10/24

3:55 pm-6:21 pm

3 stops50h 26m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 17 results
1
2

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, October is the cheapest month in which you can book a flight from Jacksonville to New Windsor (average of $109). Flying from Jacksonville to New Windsor in December is currently the most expensive (average of $202). 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?

    Allegiant Air can get you from Jacksonville to New Windsor in just under 19h 55m. 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, October is the cheapest month in which you can book a flight from Jacksonville to New Windsor (average of $109). Flying from Jacksonville to New Windsor in December is currently the most expensive (average of $202). 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 LaGuardia flights
Fort Lauderdale to Newark flights
Fort Lauderdale to John F Kennedy Intl flights
Miami to LaGuardia flights
Miami to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
Tampa to LaGuardia flights
Miami to Newark flights
Tampa to John F Kennedy Intl flights
Orlando to LaGuardia flights
Tampa to Newark flights
West Palm Beach to John F Kennedy Intl flights
Orlando to Newark flights
West Palm Beach to Newark flights
Jacksonville to John F Kennedy Intl flights
West Palm Beach to LaGuardia flights
Jacksonville to LaGuardia flights
Jacksonville to Newark flights
Orlando to Islip flights
Fort Myers to John F Kennedy Intl flights
Fort Myers to Newark flights
Sarasota to LaGuardia flights
Tampa to Islip flights
Tampa to Buffalo flights
Sarasota to John F Kennedy Intl flights
Orlando to White Plains flights
Orlando to Buffalo flights
Sarasota to Newark flights
Orlando to Stewart flights
Tampa to White Plains flights
Fort Myers to LaGuardia flights
Fort Lauderdale to Buffalo flights
Pensacola to LaGuardia flights
Orlando to Albany flights
Orlando to Rochester flights
Orlando to Syracuse flights
Fort Lauderdale to White Plains flights
West Palm Beach to Islip flights
Fort Lauderdale to Islip flights
Pensacola to John F Kennedy Intl flights
Tampa to Stewart flights
Fort Lauderdale to Stewart flights
West Palm Beach to White Plains flights
Pensacola to Newark flights
Gainesville to Newark flights
Tampa to Rochester flights
Gainesville to John F Kennedy Intl flights
Fort Myers to White Plains flights
Panama City to LaGuardia flights
Tampa to Albany 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.