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Stewart

$99+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SWF
Aug 24 — Aug 311
Mon 8/24
Mon 8/31
1 adult, Economy
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Cheap 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 July 25, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/25. 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 12/23:55 pm
JAX
-
SWF
1 stop26h 04m
Multiple Airlines
Thu 12/106:49 pm
SWF
-
JAX
1 stop13h 51m
Multiple Airlines
Deal found 7/25$217
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 12/23:55 pm
JAX
-
SWF
1 stop26h 04m
Multiple Airlines
Sun 12/66:49 pm
SWF
-
JAX
1 stop13h 51m
Multiple Airlines
Deal found 7/25$224
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 10/26:46 pm
JAX
-
SWF
2 stops40h 12m
Multiple Airlines
Thu 10/810:18 am
SWF
-
JAX
1 stop22h 07m
Multiple Airlines
Deal found 7/24$226
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:38 pm
JAX
-
SWF
1 stop21h 03m
Multiple Airlines
Sun 9/67:30 pm
SWF
-
JAX
1 stop20h 56m
Multiple Airlines
Deal found 7/21$233
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:05 pm
JAX
-
SWF
2 stops15h 18m
Multiple Airlines
Sun 9/67:30 pm
SWF
-
JAX
1 stop20h 56m
Multiple Airlines
Deal found 7/21$236
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:50 pm
JAX
-
SWF
1 stop17h 58m
Multiple Airlines
Sun 11/111:58 am
SWF
-
JAX
1 stop20h 42m
Multiple Airlines
Deal found 7/21$239
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 11/43:50 pm
JAX
-
SWF
1 stop18h 20m
Multiple Airlines
Sun 11/812:00 pm
SWF
-
JAX
1 stop20h 40m
Multiple Airlines
Deal found 7/24$244
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 10/73:50 pm
JAX
-
SWF
1 stop17h 38m
Multiple Airlines
Sun 10/1111:53 am
SWF
-
JAX
1 stop20h 32m
Multiple Airlines
Deal found 7/23$248
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Tue 12/15:06 pm
JAX
-
SWF
1 stop18h 33m
Multiple Airlines
Thu 12/106:49 pm
SWF
-
JAX
1 stop13h 51m
Multiple Airlines
Deal found 7/25$251
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Tue 12/15:06 pm
JAX
-
SWF
1 stop18h 33m
Multiple Airlines
Sun 12/66:49 pm
SWF
-
JAX
1 stop13h 51m
Multiple Airlines
Deal found 7/25$258
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 8/229:38 pm
JAX
-
SWF
1 stop14h 32m
Multiple Airlines
Thu 10/1510:18 am
SWF
-
JAX
1 stop22h 07m
Multiple Airlines
Deal found 7/25$278

Find 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 July 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$214
(Kiwi.com)

One-way from

$99
(Kiwi.com)

Popular in

April

Cheapest in

January

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 ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 25, 2026.
Use the filters below to find and compare flights from Jacksonville to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Wed 10/28

3:50 pm-9:48 am

1 stop17h 58m

New Windsor Stewart

Sun 11/1

11:58 am-8:40 am

1 stop20h 42m

$239

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sat 8/15

9:38 pm-9:38 am

1 stop12h 00m

New Windsor Stewart

Fri 8/21

5:39 pm-2:17 pm

2 stops44h 38m

$391

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Tue 12/1

5:06 pm-11:39 am

1 stop18h 33m

New Windsor Stewart

Mon 12/21

12:16 pm-8:41 pm

2 stops32h 25m

$435

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Wed 12/23

3:55 pm-11:17 am

1 stop19h 22m

New Windsor Stewart

Sun 12/27

12:07 pm-8:40 am

1 stop20h 33m

$675

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 10/30

9:20 am-11:39 am

2 stops26h 19m

New Windsor Stewart

Mon 11/2

12:16 pm-9:40 am

2 stops21h 24m

$783
Quickest round-trip

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Tue 8/11

9:03 pm-11:25 am

1 stop14h 22m

New Windsor Stewart

Thu 8/13

10:33 am-8:08 pm

2 stops9h 35m

$788

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 10/23

9:20 am-11:39 am

2 stops26h 19m

New Windsor Stewart

Mon 10/26

12:16 pm-9:40 am

2 stops21h 24m

$798

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 10/2

9:05 am-11:39 am

2 stops26h 34m

New Windsor Stewart

Sun 10/4

10:56 am-8:28 pm

2 stops9h 32m

$813

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Tue 8/18

2:15 pm-11:25 am

1 stop21h 10m

New Windsor Stewart

Fri 8/21

12:17 pm-8:45 am

2 stops20h 28m

$838

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 10/1

9:10 am-11:36 am

2 stops26h 26m

New Windsor Stewart

Sat 10/3

12:39 pm-8:25 am

3 stops19h 46m

$869

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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.

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?

    Breeze Airways can get you from Jacksonville to New Windsor in just under 26h 19m. 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.

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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