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$141+ 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 6/20. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — JAX
May 7 — May 141
Thu 5/7
Thu 5/14
1 adult, Economy
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Cheap 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 April 7, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/3. 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 8/2912:05 pm
SWF
-
JAX
1 stop20h 33m
Breeze Airways
Tue 9/19:03 pm
JAX
-
SWF
1 stop14h 22m
Breeze Airways
Deal found 4/3$238
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 8/1912:05 pm
SWF
-
JAX
1 stop20h 33m
Breeze Airways
Tue 8/259:03 pm
JAX
-
SWF
1 stop14h 22m
Breeze Airways
Deal found 4/5$243
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 5/2712:05 pm
SWF
-
JAX
1 stop20h 33m
Breeze Airways
Tue 6/29:03 pm
JAX
-
SWF
1 stop14h 22m
Breeze Airways
Deal found 4/5$287
This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
Sun 10/411:48 am
SWF
-
JAX
1 stop20h 37m
Multiple Airlines
Sat 10/103:55 pm
JAX
-
SWF
1 stop19h 13m
Multiple Airlines
Deal found 4/2$329
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 6/2712:05 pm
SWF
-
JAX
1 stop20h 33m
Multiple Airlines
Wed 7/19:38 pm
JAX
-
SWF
1 stop12h 00m
Multiple Airlines
Deal found 4/2$345
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 6/512:17 pm
SWF
-
JAX
2 stops20h 28m
Breeze Airways
Tue 6/99:03 pm
JAX
-
SWF
1 stop14h 22m
Breeze Airways
Deal found 4/5$346
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 10/312:39 pm
SWF
-
JAX
1 stop19h 59m
Multiple Airlines
Sat 10/103:55 pm
JAX
-
SWF
1 stop19h 13m
Multiple Airlines
Deal found 4/2$347
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 7/210:28 am
SWF
-
JAX
2 stops21h 29m
Multiple Airlines
Sat 7/119:38 pm
JAX
-
SWF
1 stop12h 00m
Multiple Airlines
Deal found 4/4$369
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 7/1812:05 pm
SWF
-
JAX
1 stop20h 33m
Multiple Airlines
Sat 7/259:38 pm
JAX
-
SWF
1 stop12h 00m
Multiple Airlines
Deal found 4/5$372
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 6/2412:05 pm
SWF
-
JAX
1 stop20h 33m
Multiple Airlines
Mon 6/298:47 am
JAX
-
SWF
2 stops8h 18m
Multiple Airlines
Deal found 4/2$379
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 7/17:46 pm
SWF
-
JAX
2 stops18h 54m
Multiple Airlines
Sat 7/119:38 pm
JAX
-
SWF
1 stop12h 00m
Multiple Airlines
Deal found 4/4$380

Find 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 April 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$287
(Kiwi.com)

One-way from

$141
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$362
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. 9% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 7, 2026.
Use the filters below to find and compare flights from New Windsor to Jacksonville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Wed 6/3

12:05 pm-8:38 am

1 stop20h 33m

Jacksonville

Sun 6/7

9:49 pm-5:05 pm

2 stops19h 16m

$551

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Wed 6/17

12:05 pm-8:38 am

1 stop20h 33m

Jacksonville

Mon 6/22

8:32 pm-5:29 pm

2 stops20h 57m

$559
Quickest round-trip

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Wed 6/24

12:05 pm-8:38 am

1 stop20h 33m

Jacksonville

Tue 6/30

9:03 pm-11:25 am

1 stop14h 22m

$588

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Sat 6/6

12:05 pm-2:40 pm

2 stops26h 35m

Jacksonville

Tue 6/9

9:03 pm-11:25 am

1 stop14h 22m

$743

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Wed 6/24

12:05 pm-2:40 pm

2 stops26h 35m

Jacksonville

Sun 6/28

3:05 pm-11:37 am

2 stops20h 32m

$953

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Wed 5/13

12:05 pm-2:40 pm

2 stops26h 35m

Jacksonville

Fri 5/15

9:37 am-11:25 am

2 stops25h 48m

$983

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Mon 4/20

12:11 pm-5:08 pm

2 stops28h 57m

Jacksonville

Thu 4/23

11:37 am-11:31 am

2 stops23h 54m

$998

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Fri 6/5

12:17 pm-8:45 am

2 stops20h 28m

Jacksonville

Sun 6/7

3:20 pm-11:37 am

3 stops20h 17m

$1,016
Cheapest one-way

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Sat 6/20

12:05 pm-8:38 am

1 stop20h 33m

$141

New WindsorJacksonville

SWF - JAX

SWFJAX

New Windsor Stewart

Sat 7/4

12:05 pm-8:38 am

1 stop20h 33m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/6

Showing 1-10 of 19 resultsSorted by cheapest first
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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 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, August is the cheapest month in which you can book a flight from New Windsor to Jacksonville (average of $73). Flying from New Windsor to Jacksonville in April is currently the most expensive (average of $142). 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 $588. 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, August is the cheapest month in which you can book a flight from New Windsor to Jacksonville (average of $73). Flying from New Windsor to Jacksonville in April is currently the most expensive (average of $142). 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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