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$97+ Cheap flights from New Windsor (SWF) to Illinois

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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORD
Ogos 25 — Sep 11
Isnin 8/25
Isnin 9/1
1 adult, Economy
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Cheap flight deals from Stewart to Illinois

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

Round-trip from

$209
(Mytrip)

One-way from

$97
(Mytrip)

Popular in

June

Cheapest in

September

Average price

$269
From New Windsor Stewart to Illinois
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One-way flight from New Windsor Stewart to Illinois
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Highest demand for flights based on searches. 11% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 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 Stewart to Illinois

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

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.
Jumaat 10/3111:31 amSWF - ORD
1 stop7h 53mMultiple Airlines
Ahad 11/27:29 pmORD - SWF
1 stop14h 42mMultiple Airlines
Deal found 8/19$209
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.
Isnin 10/611:01 amSWF - STL
1 stop24h 01mMultiple Airlines
Khamis 10/910:57 amSTL - SWF
1 stop22h 54mMultiple Airlines
Deal found 8/19$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.
Isnin 10/611:01 amSWF - STL
1 stop24h 01mMultiple Airlines
Ahad 10/1210:57 amSTL - SWF
1 stop22h 14mMultiple Airlines
Deal found 8/19$222
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.
Jumaat 10/312:11 pmSWF - ORD
1 stop11h 37mMultiple Airlines
Ahad 10/54:45 pmORD - SWF
1 stop16h 26mMultiple Airlines
Deal found 8/19$224
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.
Jumaat 10/1711:31 amSWF - ORD
1 stop13h 14mMultiple Airlines
Ahad 10/197:29 pmORD - SWF
1 stop13h 42mMultiple Airlines
Deal found 8/19$232
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.
Jumaat 10/1011:41 amSWF - ORD
1 stop13h 04mMultiple Airlines
Ahad 10/127:29 pmORD - SWF
1 stop13h 42mMultiple Airlines
Deal found 8/18$244
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Khamis 9/117:12 pmSWF - ORD
2 stops16h 19mMultiple Airlines
Sabtu 9/135:45 pmORD - SWF
1 stop23h 37mMultiple Airlines
Deal found 8/18$284
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.
Ahad 10/57:11 pmSWF - STL
2 stops20h 53mMultiple Airlines
Khamis 10/910:57 amSTL - SWF
1 stop22h 54mMultiple Airlines
Deal found 8/19$285
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.
Ahad 10/57:11 pmSWF - STL
2 stops20h 53mMultiple Airlines
Ahad 10/1210:57 amSTL - SWF
1 stop22h 14mMultiple Airlines
Deal found 8/19$291
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.
Khamis 10/97:11 pmSWF - STL
2 stops16h 26mMultiple Airlines
Ahad 10/1210:57 amSTL - SWF
1 stop22h 14mMultiple Airlines
Deal found 8/19$307
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.
Isnin 10/611:01 amSWF - STL
1 stop24h 01mMultiple Airlines
Sabtu 10/117:00 pmSTL - SWF
2 stops22h 21mMultiple Airlines
Deal found 8/19$328
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.
Jumaat 10/36:39 pmSWF - STL
2 stops40h 23mMultiple Airlines
Khamis 10/910:57 amSTL - SWF
1 stop22h 54mMultiple Airlines
Deal found 8/19$344

Cheapflights Fare Finder

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

Fly from

Stewart

Fly to

Illinois

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Jumaat 10/31

11:31 am-1:03 am

1 stop14h 32m

Chicago O'Hare Intl

Ahad 11/2

7:29 pm-11:11 am

1 stop14h 42m

$209

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Isnin 10/6

11:01 am-10:02 am

1 stop24h 01m

Lambert-St Louis

Khamis 10/9

10:57 am-10:51 am

1 stop22h 54m

$217

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Isnin 10/6

11:01 am-10:02 am

1 stop24h 01m

Lambert-St Louis

Ahad 10/12

10:57 am-10:11 am

1 stop22h 14m

$222

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Jumaat 11/14

11:01 am-11:42 pm

1 stop13h 41m

Chicago O'Hare Intl

Ahad 11/16

5:59 pm-11:11 am

1 stop16h 12m

$224

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Jumaat 10/24

11:31 am-11:45 pm

1 stop13h 14m

Chicago O'Hare Intl

Ahad 10/26

7:29 pm-2:11 pm

1 stop17h 42m

$224

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Jumaat 10/3

12:11 pm-10:48 pm

1 stop11h 37m

Chicago O'Hare Intl

Ahad 10/5

4:45 pm-10:11 am

1 stop16h 26m

$224

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Isnin 10/6

11:01 am-11:45 pm

1 stop13h 44m

Chicago O'Hare Intl

Khamis 10/9

7:29 pm-10:51 am

1 stop14h 22m

$224

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Jumaat 10/17

11:31 am-11:45 pm

1 stop13h 14m

Chicago O'Hare Intl

Ahad 10/19

7:29 pm-10:11 am

1 stop13h 42m

$224

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Ahad 10/5

7:11 pm-3:04 pm

2 stops20h 53m

Lambert-St Louis

Khamis 10/9

10:57 am-10:51 am

1 stop22h 54m

$285

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Ahad 10/5

7:11 pm-3:04 pm

2 stops20h 53m

Lambert-St Louis

Ahad 10/12

10:57 am-10:11 am

1 stop22h 14m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 49 results
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Best time to book a flight from Stewart to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois

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

Currently, August is the cheapest month in which you can book a flight from New Windsor to Illinois (average of $245). Flying from New Windsor to Illinois in March is currently the most expensive (average of $321). 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 Illinois. 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 from for flights from New Windsor to Illinois?

    Most people fly from New Windsor Stewart (SWF) if they book a flight from New Windsor to Illinois. New Windsor Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

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

    Allegiant Air can get you from New Windsor to Illinois in just under 15h 09m. Your travel time can differ by up to . The distance from New Windsor to Illinois is about 813 mi.

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

    While some choose either New Windsor Stewart - Lambert-St Louis or New Windsor Stewart - Chicago Midway, New Windsor Stewart - Chicago O'Hare Intl is the most popular route from New Windsor to Illinois.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Illinois 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 Illinois?

    Currently, August is the cheapest month in which you can book a flight from New Windsor to Illinois (average of $245). Flying from New Windsor to Illinois in March is currently the most expensive (average of $321). 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

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