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$95+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORD
Dec 24 — Dec 311
Wed 12/24
Wed 12/31
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 November 24, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$224
(Mytrip)

One-way from

$95
(Mytrip)

Popular in

August

Cheapest in

January

Average price

$236
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
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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. 8% potential increase in price ($21 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 November 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 November 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
Fri 12/196:56 pmSWF - ORD
1 stop30h 34mMultiple Airlines
Sun 1/48:09 pmORD - SWF
1 stop14h 53mMultiple Airlines
Deal found 11/23$311
This Kiwi.com deal was found by Cheapflights users on 11/22. 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 12/76:28 pmSWF - ORD
2 stops28h 20mMultiple Airlines
Thu 12/115:00 amORD - SWF
1 stop29h 37mMultiple Airlines
Deal found 11/22$335
This Mytrip deal was found by Cheapflights users on 11/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:27 pmSWF - ORD
1 stop8h 34mMultiple Airlines
Sun 12/71:34 pmORD - SWF
2 stops21h 03mMultiple Airlines
Deal found 11/23$338
This Mytrip deal was found by Cheapflights users on 11/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:09 amSWF - PIA
1 stop7h 41mAllegiant Air
Fri 12/198:12 pmPIA - SWF
1 stop11h 43mAllegiant Air
Deal found 11/24$361
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Thu 12/1811:43 amSWF - ORD
1 stop22h 09mMultiple Airlines
Sun 1/48:09 pmORD - SWF
1 stop14h 53mMultiple Airlines
Deal found 11/24$362
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Thu 12/1811:43 amSWF - MDW
1 stop11h 15mMultiple Airlines
Sun 1/42:16 pmMDW - SWF
1 stop20h 46mMultiple Airlines
Deal found 11/24$363
This Kiwi.com deal was found by Cheapflights users on 11/21. 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.
Thu 12/1811:43 amSWF - STL
1 stop11h 50mMultiple Airlines
Fri 12/198:37 pmSTL - SWF
1 stop11h 18mMultiple Airlines
Deal found 11/21$371
This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
Mon 12/812:27 pmSWF - ORD
1 stop23h 41mMultiple Airlines
Fri 12/129:14 pmORD - SWF
2 stops36h 49mMultiple Airlines
Deal found 11/23$393
This Kiwi.com deal was found by Cheapflights users on 11/22. 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.
Mon 12/228:25 pmSWF - STL
1 stop15h 31mMultiple Airlines
Mon 12/294:27 pmSTL - SWF
1 stop17h 36mMultiple Airlines
Deal found 11/22$397
This Kiwi.com deal was found by Cheapflights users on 11/22. 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 12/245:34 pmSWF - EVV
1 stop24h 06mAllegiant Air
Tue 12/308:42 pmEVV - SWF
1 stop19h 02mAllegiant Air
Deal found 11/22$417
This Kiwi.com deal was found by Cheapflights users on 11/22. 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 12/2311:43 amSWF - STL
1 stop11h 50mMultiple Airlines
Wed 12/244:27 pmSTL - SWF
1 stop17h 36mMultiple Airlines
Deal found 11/22$422
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Mon 12/227:10 pmSWF - ORD
1 stop14h 52mMultiple Airlines
Tue 12/3010:22 pmORD - SWF
2 stops17h 22mMultiple Airlines
Deal found 11/24$425

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 November 24, 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

Fri 1/30

11:09 am-8:54 pm

1 stop10h 45m

Chicago O'Hare Intl

Sun 2/1

5:32 pm-10:19 am

1 stop15h 47m

$224

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/9

11:09 am-8:54 pm

1 stop10h 45m

Chicago O'Hare Intl

Sun 1/11

5:32 pm-10:19 am

1 stop15h 47m

$225

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/23

11:09 am-7:17 pm

1 stop9h 08m

Chicago O'Hare Intl

Sun 1/25

5:32 pm-10:19 am

1 stop15h 47m

$239

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Sun 2/1

12:13 pm-9:21 am

1 stop22h 08m

Lambert-St Louis

Wed 2/4

4:45 pm-11:08 am

1 stop17h 23m

$253

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/16

11:09 am-7:17 pm

1 stop9h 08m

Chicago O'Hare Intl

Sun 1/18

5:32 pm-10:19 am

1 stop15h 47m

$290

New WindsorPeoria

SWF - PIA

SWFPIA

New Windsor Stewart

Thu 12/11

11:09 am-5:50 pm

1 stop7h 41m

Greater Peoria

Fri 12/19

8:12 pm-8:55 am

1 stop11h 43m

$361

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 12/18

11:43 am-9:58 pm

1 stop11h 15m

Chicago Midway

Sun 1/4

2:16 pm-12:02 pm

1 stop20h 46m

$363

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Thu 12/18

11:43 am-10:33 pm

1 stop11h 50m

Lambert-St Louis

Fri 12/19

8:37 pm-8:55 am

1 stop11h 18m

$371

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Mon 12/22

8:25 pm-10:56 am

1 stop15h 31m

Lambert-St Louis

Mon 12/29

4:27 pm-11:03 am

1 stop17h 36m

$397

New WindsorEvansville

SWF - EVV

SWFEVV

New Windsor Stewart

Wed 12/24

5:34 pm-4:40 pm

1 stop24h 06m

Evansville Dress Regional

Tue 12/30

8:42 pm-4:44 pm

1 stop19h 02m

$417

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 55 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, May is the cheapest month in which you can book a flight from New Windsor to Illinois (average of $55). Flying from New Windsor to Illinois in July is currently the most expensive (average of $126). 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 7h 41m. 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 Greater Rockford, 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, May is the cheapest month in which you can book a flight from New Windsor to Illinois (average of $55). Flying from New Windsor to Illinois in July is currently the most expensive (average of $126). 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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