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Stewart

$144+ 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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — SWF
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap 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 3, 2025.

Round-trip from

$390
(Mytrip)

One-way from

$144
(Mytrip)

Popular in

December

Cheapest in

February

Average price

$286
From Jacksonville to New Windsor Stewart
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One-way flight from Jacksonville to New Windsor Stewart
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Highest demand for flights based on searches. 5% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find 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 3, 2025.

This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/195:48 pmJAX - SWF
2 stops16h 23mMultiple Airlines
Sun 10/267:11 pmSWF - JAX
2 stops22h 32mMultiple Airlines
Deal found 7/2$383
This Mytrip deal was found by Cheapflights users on 7/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/189:45 pmJAX - SWF
2 stops19h 13mAllegiant Air
Sat 7/2611:03 amSWF - JAX
2 stops21h 51mAllegiant Air
Deal found 7/2$390
This KAYAK deal was found by Cheapflights users on 7/1. 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 7/242:08 pmJAX - SWF
2 stops22h 40mBreeze Airways
Sun 7/277:52 pmSWF - JAX
2 stops21h 09mBreeze Airways
Deal found 7/1$751

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 3, 2025.
Use the filters below to find and compare flights from Jacksonville to New Windsor that are best for you.

Fly from

Jacksonville

Fly to

Stewart

Route

Depart

Return

Price

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 7/18

9:45 pm-4:58 pm

2 stops19h 13m

New Windsor Stewart

Sat 7/26

11:03 am-8:54 am

2 stops21h 51m

$390

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 7/18

9:45 pm-4:58 pm

2 stops19h 13m

New Windsor Stewart

Sun 7/20

7:52 pm-2:29 pm

2 stops18h 37m

$434

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Thu 7/24

2:08 pm-12:48 pm

2 stops22h 40m

New Windsor Stewart

Sun 7/27

7:52 pm-5:01 pm

2 stops21h 09m

$751

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sun 7/27

8:26 pm-7:06 pm

2 stops22h 40m

$144

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Fri 7/25

9:45 pm-4:58 pm

2 stops19h 13m

$186

JacksonvilleNew Windsor

JAX - SWF

JAXSWF

Jacksonville

Sun 7/20

2:08 pm-12:48 pm

2 stops22h 40m

$442

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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, October is the cheapest month in which you can book a flight from Jacksonville to New Windsor (average of $109). Flying from Jacksonville to New Windsor in August is currently the most expensive (average of $222). 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 JAX to SWF?

Find hourly flight availability from Jacksonville to Stewart. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Jacksonville to New Windsor as you normally would.

Reviews of airlines servicing Stewart

Get insights into the airlines that provide service to Stewart. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Stewart. Reviews last updated July 3, 2025.
See what other customers who have flown with Breeze Airways and Allegiant Air from Jacksonville to New Windsor have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
183 reviews

Overall

8.1

Food

6.8

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
183 reviews
Breeze Airways
8.1
Very good
183 reviews

Overall

8.1

Food

6.8

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Allegiant Air
7.3
Good
708 reviews
Breeze Airways
8.1
Very good
183 reviews

Overall

8.1

Food

6.8

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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.

  • 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, October is the cheapest month in which you can book a flight from Jacksonville to New Windsor (average of $109). Flying from Jacksonville to New Windsor in August is currently the most expensive (average of $222). 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?

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