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$209+ 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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — JAX
Feb 17 — Feb 241
Tue 2/17
Tue 2/24
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 January 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$314
(Kiwi.com)

One-way from

$209
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$225
Provider with most accurate pricing for New Windsor Stewart-Jacksonville flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-Jacksonville flights.
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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. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1312:05 pm
SWF
-
JAX
1 stop20h 33m
Breeze Airways
Tue 6/169:03 pm
JAX
-
SWF
1 stop14h 22m
Breeze Airways
Deal found 1/15$314
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
Sat 5/2312:05 pm
SWF
-
JAX
1 stop20h 33m
Breeze Airways
Tue 5/269:03 pm
JAX
-
SWF
1 stop14h 22m
Breeze Airways
Deal found 1/18$320
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1212:15 pm
SWF
-
JAX
2 stops20h 30m
Breeze Airways
Tue 6/169:03 pm
JAX
-
SWF
1 stop14h 22m
Breeze Airways
Deal found 1/15$397
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
Wed 6/1712:05 pm
SWF
-
JAX
1 stop20h 33m
Multiple Airlines
Sun 6/219:49 pm
JAX
-
SWF
2 stops19h 16m
Multiple Airlines
Deal found 1/18$406
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1110:28 am
SWF
-
JAX
2 stops22h 29m
Multiple Airlines
Tue 6/169:03 pm
JAX
-
SWF
1 stop14h 22m
Multiple Airlines
Deal found 1/15$407
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
Thu 5/2110:28 am
SWF
-
JAX
2 stops22h 29m
Multiple Airlines
Tue 5/269:03 pm
JAX
-
SWF
1 stop14h 22m
Multiple Airlines
Deal found 1/18$454
This Kiwi.com deal was found by Cheapflights users on 1/17. 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.
Wed 5/2012:05 pm
SWF
-
JAX
1 stop20h 33m
Multiple Airlines
Sun 5/249:37 am
JAX
-
SWF
2 stops9h 43m
Multiple Airlines
Deal found 1/17$555
This Kiwi.com deal was found by Cheapflights users on 1/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:05 pm
SWF
-
JAX
1 stop20h 33m
Multiple Airlines
Sun 7/59:49 pm
JAX
-
SWF
2 stops19h 10m
Multiple Airlines
Deal found 1/16$682

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 January 18, 2026.
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

Sat 6/13

12:05 pm-8:38 am

1 stop20h 33m

Jacksonville

Tue 6/16

9:03 pm-11:25 am

1 stop14h 22m

$314

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Sat 5/23

12:05 pm-8:38 am

1 stop20h 33m

Jacksonville

Tue 5/26

9:03 pm-11:25 am

1 stop14h 22m

$320

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Fri 6/12

12:15 pm-8:45 am

2 stops20h 30m

Jacksonville

Tue 6/16

9:03 pm-11:25 am

1 stop14h 22m

$397

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Wed 6/17

12:05 pm-8:38 am

1 stop20h 33m

Jacksonville

Sun 6/21

9:49 pm-5:05 pm

2 stops19h 16m

$406

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Thu 6/11

10:28 am-8:57 am

2 stops22h 29m

Jacksonville

Tue 6/16

9:03 pm-11:25 am

1 stop14h 22m

$407

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Thu 5/21

10:28 am-8:57 am

2 stops22h 29m

Jacksonville

Tue 5/26

9:03 pm-11:25 am

1 stop14h 22m

$454

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Wed 5/20

12:05 pm-8:38 am

1 stop20h 33m

Jacksonville

Sun 5/24

9:37 am-7:20 pm

2 stops9h 43m

$555

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Wed 7/1

12:05 pm-8:38 am

1 stop20h 33m

Jacksonville

Sun 7/5

9:49 pm-4:59 pm

2 stops19h 10m

$682

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Mon 2/16

12:11 pm-5:08 pm

2 stops28h 57m

$209

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Thu 4/30

11:45 am-10:01 am

2 stops22h 16m

$226

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 16 results
1
2

Compare providers for flights from Stewart to Jacksonville

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 Stewart to Jacksonville in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 New Windsor-Jacksonville flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Jacksonville flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Jacksonville flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Jacksonville flights, Cheapflights users trust Expedia the most. Expedia 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 New Windsor-Jacksonville 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 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, February is the cheapest month in which you can book a flight from New Windsor to Jacksonville (average of $68). Flying from New Windsor to Jacksonville in October is currently the most expensive (average of $126). 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 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 33m. Breeze Airways provides one of the quickest options available for as low as $314. There are 869 mi between New Windsor and Jacksonville.

  • 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, February is the cheapest month in which you can book a flight from New Windsor to Jacksonville (average of $68). Flying from New Windsor to Jacksonville in October is currently the most expensive (average of $126). 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
Fernandina Beach
Kingsland
Waycross
Yulee

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