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Stewart

$99+ Cheap flights from Illinois to New Windsor (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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Illinois to Stewart

Keep the following information in mind while searching for Illinois to Stewart flight deals. Data was last updated August 20, 2025.

Round-trip from

$217
(Kiwi.com)

One-way from

$99
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$218
From Illinois to New Windsor Stewart
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One-way flight from Illinois to New Windsor Stewart
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Highest demand for flights based on searches. 3% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Illinois to Stewart

Cheapest flights from Illinois to Stewart
Explore the most affordable flight options available from Illinois to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/910:57 amSTL - SWF
1 stop22h 54mMultiple Airlines
Mon 10/1311:01 amSWF - STL
1 stop24h 01mMultiple Airlines
Deal found 8/17$217
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1910:57 amSTL - SWF
1 stop22h 14mMultiple Airlines
Fri 10/2411:31 amSWF - STL
1 stop31h 14mMultiple Airlines
Deal found 8/19$222
This Mytrip deal was found by Cheapflights users on 8/18. 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.
Thu 10/167:29 pmORD - SWF
1 stop14h 12mMultiple Airlines
Mon 10/2011:01 amSWF - ORD
1 stop8h 23mMultiple Airlines
Deal found 8/18$224
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1610:57 amSTL - SWF
1 stop22h 44mMultiple Airlines
Mon 10/2011:01 amSWF - STL
1 stop24h 01mMultiple Airlines
Deal found 8/19$228
This Mytrip deal was found by Cheapflights users on 8/20. 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.
Sun 11/95:59 pmORD - SWF
1 stop16h 12mMultiple Airlines
Fri 11/1411:01 amSWF - ORD
1 stop13h 41mMultiple Airlines
Deal found 8/20$228
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Thu 10/231:26 pmORD - SWF
2 stops20h 15mMultiple Airlines
Mon 10/273:01 pmSWF - ORD
1 stop11h 02mMultiple Airlines
Deal found 8/19$232
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/712:20 pmSTL - SWF
1 stop22h 17mMultiple Airlines
Fri 12/127:30 pmSWF - STL
2 stops19h 23mMultiple Airlines
Deal found 8/19$260
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/39:10 amMLI - SWF
1 stop9h 21mAllegiant Air
Tue 10/711:16 amSWF - MLI
1 stop21h 24mAllegiant Air
Deal found 8/20$337
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/43:13 pmMLI - SWF
1 stop26h 08mAllegiant Air
Tue 10/711:16 amSWF - MLI
1 stop21h 24mAllegiant Air
Deal found 8/20$356
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/26:44 pmORD - SWF
1 stop15h 37mMultiple Airlines
Sun 10/55:45 pmSWF - ORD
2 stops25h 39mMultiple Airlines
Deal found 8/17$358
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/287:46 pmORD - SWF
1 stop13h 21mMultiple Airlines
Fri 8/291:55 pmSWF - ORD
1 stop30h 12mMultiple Airlines
Deal found 8/20$402
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/317:46 pmORD - SWF
1 stop13h 26mMultiple Airlines
Mon 9/11:55 pmSWF - ORD
1 stop21h 36mMultiple Airlines
Deal found 8/19$407

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 August 20, 2025.
Use the filters below to find and compare flights from Illinois to New Windsor that are best for you.

Fly from

Illinois

Fly to

Stewart

Route

Depart

Return

Price

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Thu 10/9

10:57 am-10:51 am

1 stop22h 54m

New Windsor Stewart

Mon 10/13

11:01 am-10:02 am

1 stop24h 01m

$217

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Sun 10/19

10:57 am-10:11 am

1 stop22h 14m

New Windsor Stewart

Fri 10/24

11:31 am-5:45 pm

1 stop31h 14m

$222

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Sun 12/7

12:20 pm-11:37 am

1 stop22h 17m

New Windsor Stewart

Fri 12/12

12:27 pm-1:53 pm

1 stop26h 26m

$222

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/23

4:45 pm-10:41 am

1 stop16h 56m

New Windsor Stewart

Mon 10/27

3:01 pm-1:03 am

1 stop11h 02m

$224

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/16

7:29 pm-10:41 am

1 stop14h 12m

New Windsor Stewart

Mon 10/20

11:01 am-6:24 pm

1 stop8h 23m

$224

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Thu 10/16

10:57 am-10:41 am

1 stop22h 44m

New Windsor Stewart

Mon 10/20

11:01 am-10:02 am

1 stop24h 01m

$228

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 11/9

5:59 pm-11:11 am

1 stop16h 12m

New Windsor Stewart

Fri 11/14

11:01 am-11:42 pm

1 stop13h 41m

$228

MolineNew Windsor

MLI - SWF

MLISWF

Moline Quad-City

Fri 10/3

9:10 am-7:31 pm

1 stop9h 21m

New Windsor Stewart

Tue 10/7

11:16 am-7:40 am

1 stop21h 24m

$337

MolineNew Windsor

MLI - SWF

MLISWF

Moline Quad-City

Sat 10/4

3:13 pm-6:21 pm

1 stop26h 08m

New Windsor Stewart

Tue 10/7

11:16 am-7:40 am

1 stop21h 24m

$356

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/2

6:44 pm-11:21 am

1 stop15h 37m

New Windsor Stewart

Sun 10/5

5:45 pm-6:24 pm

2 stops25h 39m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 44 results
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Best time to book a flight from Illinois to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Illinois 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 Illinois to New Windsor

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

Currently, October is the cheapest month in which you can book a flight from Illinois to New Windsor (average of $109). Flying from Illinois to New Windsor in December is currently the most expensive (average of $202). 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 IL to SWF?

Find hourly flight availability from Illinois 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 August 20, 2025.

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

Related info for your journey

Find useful and relevant information for your journey from Illinois to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Illinois?

    For a flight from Illinois to New Windsor, you will be flying into Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

  • How long is the flight from Illinois to New Windsor?

    Allegiant Air can get you from Illinois to New Windsor in just under 9h 21m. Your travel time can differ by up to . The distance between Illinois and New Windsor is about 847 mi.

  • What are the most popular routes from Illinois to New Windsor?

    When deciding which route to take from Illinois to New Windsor consider Chicago O'Hare Intl - New Windsor Stewart, Lambert-St Louis - New Windsor Stewart or Greater Peoria - New Windsor Stewart as they are the most popular.

  • Can I find deals for flights from Illinois to Stewart that include hotel bookings?

    Yes. In addition to deals on Illinois to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Stewart.

  • Can I find deals for business class flights from Illinois to Stewart?

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Illinois to New Windsor (average of $109). Flying from Illinois to New Windsor in December is currently the most expensive (average of $202). 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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