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$183+ Cheap flights from New Windsor to Jacksonville (SWF - JAX)

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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — JAX
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Stewart to Jacksonville

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Jacksonville (JAX). 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 16, 2025.

Round-trip from

$684
(Mytrip)

One-way from

$183
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$237
From New Windsor Stewart to Jacksonville
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One-way flight from New Windsor Stewart to Jacksonville
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Highest demand for flights based on searches. 3% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Stewart to Jacksonville

Cheapest flights from Stewart to Jacksonville
Explore the most affordable flight options available from Stewart to Jacksonville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

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.
Wed 11/2612:17 pmSWF - JAX
2 stops20h 38mAllegiant Air
Sun 11/308:51 amJAX - SWF
2 stops24h 15mAllegiant Air
Deal found 9/13$684
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.
Fri 10/3112:24 pmSWF - JAX
3 stops20h 34mBreeze Airways
Sun 11/211:18 amJAX - SWF
2 stops24h 26mBreeze Airways
Deal found 9/14$771
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.
Tue 11/2511:36 amSWF - JAX
2 stops22h 11mAllegiant Air
Sun 11/308:51 amJAX - SWF
2 stops24h 15mAllegiant Air
Deal found 9/14$789
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.
Fri 10/2412:24 pmSWF - JAX
3 stops20h 34mBreeze Airways
Sun 10/2611:40 amJAX - SWF
2 stops24h 04mBreeze Airways
Deal found 9/14$858
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.
Fri 10/312:24 pmSWF - JAX
3 stops20h 34mBreeze Airways
Sun 10/511:18 amJAX - SWF
2 stops24h 26mBreeze Airways
Deal found 9/14$864
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:24 pmSWF - JAX
3 stops21h 29mBreeze Airways
Sun 12/1411:18 amJAX - SWF
2 stops24h 26mBreeze Airways
Deal found 9/15$873
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2112:24 pmSWF - JAX
3 stops20h 34mBreeze Airways
Sun 11/2311:40 amJAX - SWF
2 stops24h 04mBreeze Airways
Deal found 9/15$877

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Jacksonville 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 16, 2025.
Use the filters below to find and compare flights from New Windsor to Jacksonville that are best for you.

Fly from

Stewart

Fly to

Jacksonville

Route

Depart

Return

Price

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Wed 11/26

12:17 pm-8:55 am

2 stops20h 38m

Jacksonville

Sun 11/30

8:51 am-9:06 am

2 stops24h 15m

$684

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Fri 10/31

12:24 pm-8:58 am

3 stops20h 34m

Jacksonville

Sun 11/2

11:18 am-11:44 am

2 stops24h 26m

$771

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Tue 11/25

11:36 am-9:47 am

2 stops22h 11m

Jacksonville

Sun 11/30

8:51 am-9:06 am

2 stops24h 15m

$789

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Fri 10/3

12:24 pm-8:58 am

3 stops20h 34m

Jacksonville

Sun 10/5

11:18 am-11:44 am

2 stops24h 26m

$864

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Fri 11/21

12:24 pm-8:58 am

3 stops20h 34m

Jacksonville

Sun 11/23

11:40 am-11:44 am

2 stops24h 04m

$877

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Fri 10/24

12:24 pm-8:58 am

3 stops20h 34m

Jacksonville

Sun 10/26

11:40 am-11:44 am

2 stops24h 04m

$878

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Fri 10/24

11:31 am-10:51 am

2 stops23h 20m

$183

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Mon 10/6

11:01 am-8:53 am

3 stops45h 52m

$184

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Sun 10/5

7:11 pm-8:36 pm

2 stops25h 25m

$197

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Sun 12/14

11:43 am-8:58 am

2 stops21h 15m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 16 results
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Best time to book a flight from Stewart to Jacksonville

Have a flexible travel schedule? Discover the best time to fly to Jacksonville from Stewart 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 New Windsor to Jacksonville

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

Currently, August is the cheapest month in which you can book a flight from New Windsor to Jacksonville (average of $278). Flying from New Windsor to Jacksonville in March is currently the most expensive (average of $365). 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.

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

Find hourly flight availability from Stewart to Jacksonville. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

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

Related info for your journey

Find useful and relevant information for your journey from Stewart to Jacksonville. 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 New Windsor to Jacksonville?

    A quick flight from New Windsor to Jacksonville can take about 20h 34m. Allegiant Air provides one of the quickest options available for as low as $771. There are 869 mi between New Windsor and Jacksonville. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Jacksonville 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 New Windsor to Jacksonville?

    Currently, August is the cheapest month in which you can book a flight from New Windsor to Jacksonville (average of $278). Flying from New Windsor to Jacksonville in March is currently the most expensive (average of $365). 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 Jacksonville?

Book flights to Jacksonville if you plan to visit one of these locations
Jacksonville Beach
Orange Park
Kingsland
Fernandina Beach
Waycross

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