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$186+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — JAX
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
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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 October 22, 2025.

This Mytrip deal was found by Cheapflights users on 10/19. 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 38mMultiple Airlines
Sun 12/79:21 pmJAX - SWF
2 stops21h 19mMultiple Airlines
Deal found 10/19$434
This Mytrip deal was found by Cheapflights users on 10/21. 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.
Mon 12/227:10 pmSWF - JAX
2 stops23h 50mAllegiant Air
Tue 12/309:29 pmJAX - SWF
2 stops19h 15mAllegiant Air
Deal found 10/21$492
This Mytrip deal was found by Cheapflights users on 10/21. 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.
Mon 12/227:10 pmSWF - JAX
2 stops23h 50mAllegiant Air
Mon 12/299:19 pmJAX - SWF
2 stops18h 41mAllegiant Air
Deal found 10/21$706
This Mytrip deal was found by Cheapflights users on 10/20. 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.
Mon 12/228:25 pmSWF - JAX
2 stops16h 45mAllegiant Air
Sat 1/39:10 amJAX - SWF
2 stops24h 49mAllegiant Air
Deal found 10/20$735
This Mytrip deal was found by Cheapflights users on 10/21. 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 12/209:45 amSWF - JAX
2 stops22h 14mAllegiant Air
Sat 12/2711:40 amJAX - SWF
2 stops22h 19mAllegiant Air
Deal found 10/21$809
This Mytrip deal was found by Cheapflights users on 10/21. 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 38mMultiple Airlines
Sun 11/303:29 pmJAX - SWF
2 stops17h 37mMultiple Airlines
Deal found 10/21$819
This Mytrip deal was found by Cheapflights users on 10/20. 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.
Mon 12/228:25 pmSWF - JAX
2 stops16h 45mAllegiant Air
Fri 12/267:00 pmJAX - SWF
2 stops24h 55mAllegiant Air
Deal found 10/20$842

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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$335
(Mytrip)

One-way from

$186
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$262
Provider with most accurate pricing for New Windsor Stewart-Jacksonville flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Jacksonville flights.
Search Deals
From New Windsor Stewart to Jacksonville
Search Deals
One-way flight from New Windsor Stewart to Jacksonville
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 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 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 October 22, 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

Thu 1/8

10:48 am-10:35 am

2 stops23h 47m

Jacksonville

Sun 1/11

9:42 pm-6:43 pm

2 stops21h 01m

$335

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Wed 11/26

12:17 pm-8:55 am

2 stops20h 38m

Jacksonville

Sun 12/7

9:21 pm-6:40 pm

2 stops21h 19m

$434

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Mon 12/22

7:10 pm-7:00 pm

2 stops23h 50m

Jacksonville

Tue 12/30

9:29 pm-4:44 pm

2 stops19h 15m

$492

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Mon 12/22

7:10 pm-7:00 pm

2 stops23h 50m

Jacksonville

Mon 12/29

9:19 pm-4:00 pm

2 stops18h 41m

$706

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Mon 12/22

8:25 pm-1:10 pm

2 stops16h 45m

Jacksonville

Sat 1/3

9:10 am-9:59 am

2 stops24h 49m

$735

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Sat 12/20

9:45 am-7:59 am

2 stops22h 14m

Jacksonville

Sat 12/27

11:40 am-9:59 am

2 stops22h 19m

$809

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Wed 11/26

12:17 pm-8:55 am

2 stops20h 38m

Jacksonville

Sun 11/30

3:29 pm-9:06 am

2 stops17h 37m

$819

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Mon 12/22

8:25 pm-1:10 pm

2 stops16h 45m

Jacksonville

Fri 12/26

7:00 pm-7:55 pm

2 stops24h 55m

$842

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Fri 11/14

11:01 am-8:58 am

2 stops21h 57m

$186

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Thu 11/13

6:14 pm-8:36 pm

2 stops26h 22m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 20 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 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 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 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 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, December is the cheapest month in which you can book a flight from New Windsor to Jacksonville (average of $63). Flying from New Windsor to Jacksonville in June is currently the most expensive (average of $113). 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 October 22, 2025.

A simple way to save on the total cost of your ticket is to fly from New Windsor to Jacksonville at noon. If you’re flexible enough to do this you can expect to save up to 35% on your trip compared to booking a flight in the morning.

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 23h 47m. Allegiant Air provides one of the quickest options available for as low as $335. 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, December is the cheapest month in which you can book a flight from New Windsor to Jacksonville (average of $63). Flying from New Windsor to Jacksonville in June is currently the most expensive (average of $113). 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

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