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Stewart

$124+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SWF
Mar 30 — Apr 61
Mon 3/30
Mon 4/6
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 February 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/27. 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 6/43:20 pm
JAX
-
SWF
2 stops17h 29m
Multiple Airlines
Sat 6/612:05 pm
SWF
-
JAX
1 stop20h 33m
Multiple Airlines
Deal found 2/27$340
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 7/189:38 pm
JAX
-
SWF
1 stop12h 00m
Multiple Airlines
Wed 7/2212:05 pm
SWF
-
JAX
1 stop20h 33m
Multiple Airlines
Deal found 2/26$353
This Kiwi.com deal was found by Cheapflights users on 2/25. 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 6/69:12 pm
JAX
-
SWF
2 stops20h 31m
Multiple Airlines
Sat 6/2012:05 pm
SWF
-
JAX
1 stop20h 33m
Multiple Airlines
Deal found 2/25$358
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 5/319:49 pm
JAX
-
SWF
2 stops19h 14m
Multiple Airlines
Sat 6/612:05 pm
SWF
-
JAX
1 stop20h 33m
Multiple Airlines
Deal found 2/26$381
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 5/219:37 am
JAX
-
SWF
2 stops9h 43m
Multiple Airlines
Sat 5/2312:05 pm
SWF
-
JAX
1 stop20h 33m
Multiple Airlines
Deal found 2/26$454
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 8/59:38 pm
JAX
-
SWF
1 stop12h 00m
Multiple Airlines
Sun 8/911:45 am
SWF
-
JAX
2 stops10h 08m
Multiple Airlines
Deal found 2/27$645
This KAYAK deal was found by Cheapflights users on 2/27. 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.
Thu 6/43:20 pm
JAX
-
SWF
3 stops20h 15m
Breeze Airways
Sat 6/612:05 pm
SWF
-
JAX
1 stop20h 33m
Breeze Airways
Deal found 2/27$757
This KAYAK deal was found by Cheapflights users on 2/24. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:37 am
JAX
-
SWF
2 stops25h 48m
Breeze Airways
Wed 6/1012:05 pm
SWF
-
JAX
1 stop20h 33m
Breeze Airways
Deal found 2/24$779
This KAYAK deal was found by Cheapflights users on 2/26. 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.
Thu 8/203:05 pm
JAX
-
SWF
2 stops20h 30m
Breeze Airways
Mon 8/2412:15 pm
SWF
-
JAX
2 stops27h 13m
Breeze Airways
Deal found 2/26$838
This KAYAK deal was found by Cheapflights users on 2/26. 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.
Sun 5/3112:07 pm
JAX
-
SWF
3 stops23h 28m
Breeze Airways
Sat 6/612:05 pm
SWF
-
JAX
1 stop20h 33m
Breeze Airways
Deal found 2/26$857

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 February 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$340
(Kiwi.com)

One-way from

$148
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$236
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
High demand for flights, 0% potential price rise
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 February 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 February 28, 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

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sat 7/18

9:38 pm-9:38 am

1 stop12h 00m

New Windsor Stewart

Wed 7/22

12:05 pm-8:38 am

1 stop20h 33m

$353

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sat 6/6

9:12 pm-5:43 pm

2 stops20h 31m

New Windsor Stewart

Sat 6/20

12:05 pm-8:38 am

1 stop20h 33m

$358

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 6/4

3:20 pm-11:35 am

3 stops20h 15m

New Windsor Stewart

Sat 6/6

12:05 pm-8:38 am

1 stop20h 33m

$757

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 8/20

3:05 pm-11:35 am

2 stops20h 30m

New Windsor Stewart

Mon 8/24

12:15 pm-3:28 pm

2 stops27h 13m

$838

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sun 5/31

12:07 pm-11:35 am

3 stops23h 28m

New Windsor Stewart

Sat 6/6

12:05 pm-8:38 am

1 stop20h 33m

$857

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 5/28

3:05 pm-11:35 am

2 stops20h 30m

New Windsor Stewart

Mon 6/1

12:15 pm-3:28 pm

2 stops27h 13m

$878

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 6/12

9:37 am-11:25 am

2 stops25h 48m

New Windsor Stewart

Mon 6/15

12:15 pm-3:28 pm

2 stops27h 13m

$890

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 5/21

3:05 pm-11:35 am

2 stops20h 30m

New Windsor Stewart

Sat 5/23

12:05 pm-2:40 pm

2 stops26h 35m

$913

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 5/22

9:37 am-11:25 am

2 stops25h 48m

New Windsor Stewart

Mon 5/25

12:15 pm-3:28 pm

2 stops27h 13m

$913

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 7/24

9:37 am-11:25 am

2 stops25h 48m

New Windsor Stewart

Tue 7/28

11:48 am-8:48 am

2 stops21h 00m

$921

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/26

Showing 1-10 of 22 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 February.
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.

Cheapflights Insights

Everything you need to know about your flight from Jacksonville to New Windsor

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

Currently, January is the cheapest month in which you can book a flight from Jacksonville to New Windsor (average of $63). Flying from Jacksonville to New Windsor in July is currently the most expensive (average of $128). 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 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 20h 15m. 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.

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

    Currently, January is the cheapest month in which you can book a flight from Jacksonville to New Windsor (average of $63). Flying from Jacksonville to New Windsor in July is currently the most expensive (average of $128). 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 New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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