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Stewart

$87+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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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 November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/205:00 amORD - SWF
1 stop28h 22mMultiple Airlines
Mon 11/2410:57 amSWF - ORD
1 stop23h 20mMultiple Airlines
Deal found 11/5$256
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/2010:53 amSTL - SWF
1 stop22h 29mMultiple Airlines
Mon 11/2410:57 amSWF - STL
2 stops28h 32mMultiple Airlines
Deal found 11/5$278
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/205:30 amMDW - SWF
2 stops27h 52mMultiple Airlines
Mon 11/247:28 pmSWF - MDW
1 stop15h 04mMultiple Airlines
Deal found 11/5$325
This Mytrip deal was found by Cheapflights users on 11/6. 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 11/2312:32 pmORD - SWF
2 stops20h 35mMultiple Airlines
Wed 11/2612:17 pmSWF - ORD
1 stop11h 56mMultiple Airlines
Deal found 11/6$328
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/245:47 pmMDW - SWF
1 stop14h 06mMultiple Airlines
Sun 11/308:41 pmSWF - MDW
2 stops37h 36mMultiple Airlines
Deal found 11/6$374
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/137:43 pmSTL - SWF
2 stops14h 20mMultiple Airlines
Thu 12/1811:43 amSWF - STL
1 stop11h 50mMultiple Airlines
Deal found 11/5$385
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/267:43 pmSTL - SWF
2 stops14h 20mMultiple Airlines
Sun 11/308:41 pmSWF - STL
1 stop28h 16mMultiple Airlines
Deal found 11/3$402
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/197:08 pmMLI - SWF
1 stop22h 52mAllegiant Air
Mon 12/227:10 pmSWF - MLI
1 stop13h 44mAllegiant Air
Deal found 11/6$464
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/197:24 pmSTL - SWF
1 stop14h 39mMultiple Airlines
Sun 11/306:04 pmSWF - STL
2 stops30h 53mMultiple Airlines
Deal found 11/6$483
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/63:18 pmORD - SWF
2 stops18h 23mMultiple Airlines
Thu 11/1311:43 amSWF - ORD
1 stop12h 23mMultiple Airlines
Deal found 11/5$483
This Mytrip deal was found by Cheapflights users on 11/4. 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.
Mon 11/178:34 amPIA - SWF
1 stop9h 18mAllegiant Air
Fri 11/217:28 pmSWF - PIA
1 stop17h 47mAllegiant Air
Deal found 11/4$521
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/76:37 pmMDW - SWF
2 stops16h 07mMultiple Airlines
Thu 12/1111:43 amSWF - MDW
1 stop11h 15mMultiple Airlines
Deal found 11/4$546

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 November 6, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$235
(Kiwi.com)

One-way from

$87
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$209
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
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From Illinois to New Windsor Stewart
Search Deals
One-way flight from Illinois to New Windsor Stewart
Search Deals
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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 November 6, 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

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/20

5:00 am-10:22 am

1 stop28h 22m

New Windsor Stewart

Mon 11/24

10:57 am-9:17 am

1 stop23h 20m

$256

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/13

8:28 am-10:11 am

2 stops24h 43m

New Windsor Stewart

Mon 11/17

12:01 pm-12:27 am

1 stop13h 26m

$259

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/8

7:52 pm-10:19 am

1 stop13h 27m

New Windsor Stewart

Sun 1/11

12:13 pm-7:45 pm

1 stop8h 32m

$263

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Thu 11/20

10:53 am-10:22 am

1 stop22h 29m

New Windsor Stewart

Mon 11/24

10:57 am-2:29 pm

2 stops28h 32m

$278

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 11/20

5:30 am-10:22 am

2 stops27h 52m

New Windsor Stewart

Mon 11/24

7:28 pm-9:32 am

1 stop15h 04m

$325

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 11/23

12:32 pm-10:07 am

2 stops20h 35m

New Windsor Stewart

Wed 11/26

12:17 pm-11:13 pm

1 stop11h 56m

$328

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

7:52 pm-10:19 am

1 stop13h 27m

New Windsor Stewart

Mon 1/19

11:09 am-6:47 pm

1 stop8h 38m

$334

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Mon 11/24

5:47 pm-8:53 am

1 stop14h 06m

New Windsor Stewart

Sun 11/30

8:41 pm-9:17 am

2 stops37h 36m

$374

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 11/26

5:30 pm-11:03 am

1 stop16h 33m

New Windsor Stewart

Sun 11/30

8:41 pm-9:17 am

2 stops37h 36m

$397

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Wed 11/26

7:43 pm-11:03 am

2 stops14h 20m

New Windsor Stewart

Sun 11/30

8:41 pm-11:57 pm

1 stop28h 16m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 48 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, January is the cheapest month in which you can book a flight from Illinois to New Windsor (average of $37). Flying from Illinois to New Windsor in July is currently the most expensive (average of $104). 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 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 22h 52m. 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 Moline Quad-City - 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, January is the cheapest month in which you can book a flight from Illinois to New Windsor (average of $37). Flying from Illinois to New Windsor in July is currently the most expensive (average of $104). 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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