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Stewart

$141+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SWF
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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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 October 16, 2025.

This Mytrip deal was found by Cheapflights users on 10/14. 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 11/1311:08 amJAX - SWF
2 stops23h 03mAllegiant Air
Sun 11/166:14 pmSWF - JAX
2 stops24h 29mAllegiant Air
Deal found 10/14$360
This Mytrip deal was found by Cheapflights users on 10/14. 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 10/233:26 pmJAX - SWF
2 stops19h 15mAllegiant Air
Sun 10/267:11 pmSWF - JAX
2 stops22h 32mAllegiant Air
Deal found 10/14$361
This Mytrip deal was found by Cheapflights users on 10/14. 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
Sun 11/26:16 pmSWF - JAX
2 stops23h 27mMultiple Airlines
Deal found 10/14$376
This Mytrip deal was found by Cheapflights users on 10/14. 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 11/611:08 amJAX - SWF
2 stops23h 33mAllegiant Air
Sun 11/96:14 pmSWF - JAX
2 stops24h 29mAllegiant Air
Deal found 10/14$452
This Mytrip deal was found by Cheapflights users on 10/14. 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 10/193:26 pmJAX - SWF
2 stops18h 45mAllegiant Air
Sun 10/267:11 pmSWF - JAX
2 stops22h 32mAllegiant Air
Deal found 10/14$454
This Mytrip deal was found by Cheapflights users on 10/16. 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 12/219:21 pmJAX - SWF
2 stops20h 59mAllegiant Air
Mon 12/228:25 pmSWF - JAX
2 stops16h 45mAllegiant Air
Deal found 10/16$500
This Mytrip deal was found by Cheapflights users on 10/15. 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.
Sat 12/208:55 amJAX - SWF
2 stops25h 24mAllegiant Air
Mon 12/227:10 pmSWF - JAX
2 stops23h 50mAllegiant Air
Deal found 10/15$605
This Mytrip deal was found by Cheapflights users on 10/15. 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.
Sun 12/219:21 pmJAX - SWF
2 stops22h 14mAllegiant Air
Sat 1/38:45 pmSWF - JAX
2 stops21h 58mAllegiant Air
Deal found 10/15$616

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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$402
(Mytrip)

One-way from

$141
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$277
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
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. 7% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 16, 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

Sun 11/2

6:16 pm-5:43 pm

2 stops23h 27m

$402

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 11/6

11:08 am-10:41 am

2 stops23h 33m

New Windsor Stewart

Sun 11/9

6:14 pm-6:43 pm

2 stops24h 29m

$466

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sun 12/21

9:21 pm-6:20 pm

2 stops20h 59m

New Windsor Stewart

Mon 12/22

8:25 pm-1:10 pm

2 stops16h 45m

$500

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sat 12/20

8:55 am-10:19 am

2 stops25h 24m

New Windsor Stewart

Mon 12/22

7:10 pm-7:00 pm

2 stops23h 50m

$605

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sun 12/21

9:21 pm-7:35 pm

2 stops22h 14m

New Windsor Stewart

Sat 1/3

8:45 pm-6:43 pm

2 stops21h 58m

$616

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 12/19

8:29 pm-7:00 pm

2 stops22h 31m

New Windsor Stewart

Mon 12/22

7:10 pm-7:00 pm

2 stops23h 50m

$620

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sun 12/21

9:21 pm-7:35 pm

2 stops22h 14m

New Windsor Stewart

Sat 12/27

8:45 pm-6:43 pm

2 stops21h 58m

$736

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sat 12/27

11:40 am-9:59 am

2 stops22h 19m

New Windsor Stewart

Mon 12/29

11:37 am-7:59 am

3 stops20h 22m

$1,192

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 12/11

11:40 am-11:37 am

2 stops23h 57m

$141

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sun 12/7

11:40 am-11:37 am

2 stops23h 57m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

Showing 1-10 of 17 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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, March is the cheapest month in which you can book a flight from Jacksonville to New Windsor (average of $68). Flying from Jacksonville to New Windsor in January is currently the most expensive (average of $134). 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 23h 33m. 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, March is the cheapest month in which you can book a flight from Jacksonville to New Windsor (average of $68). Flying from Jacksonville to New Windsor in January is currently the most expensive (average of $134). 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

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