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Stewart

$89+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/26. 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 12/116:15 amORD - SWF
1 stop28h 22mMultiple Airlines
Mon 12/1512:24 pmSWF - ORD
2 stops10h 24mMultiple Airlines
Deal found 11/26$237
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.
Sun 12/75:00 amORD - SWF
1 stop29h 37mMultiple Airlines
Fri 12/1212:27 pmSWF - ORD
1 stop12h 42mMultiple Airlines
Deal found 11/24$238
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.
Sun 12/75:00 amORD - SWF
1 stop29h 37mMultiple Airlines
Mon 12/87:30 pmSWF - ORD
2 stops44h 01mMultiple Airlines
Deal found 11/24$262
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.
Sun 12/75:00 amORD - SWF
1 stop29h 37mMultiple Airlines
Sun 12/1411:43 amSWF - ORD
1 stop26h 33mMultiple Airlines
Deal found 11/24$267
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.
Sun 12/75:00 amORD - SWF
1 stop29h 37mMultiple Airlines
Thu 12/1111:09 amSWF - ORD
2 stops14h 00mMultiple Airlines
Deal found 11/24$269
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/103:30 pmSTL - SWF
1 stop18h 33mMultiple Airlines
Fri 12/127:30 pmSWF - STL
1 stop28h 03mMultiple Airlines
Deal found 11/25$273
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 12/87:20 amORD - SWF
1 stop10h 20mMultiple Airlines
Fri 12/1212:27 pmSWF - ORD
1 stop12h 42mMultiple Airlines
Deal found 11/24$309
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.
Sat 12/67:43 pmSTL - SWF
2 stops14h 20mMultiple Airlines
Mon 12/157:30 pmSWF - STL
1 stop28h 03mMultiple Airlines
Deal found 11/24$406
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.
Sat 12/207:43 pmSTL - SWF
2 stops14h 20mMultiple Airlines
Mon 12/228:25 pmSWF - STL
1 stop15h 31mMultiple Airlines
Deal found 11/24$449
This Booking.com deal was found by Cheapflights users on 11/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/72:47 pmSTL - SWF
1 stop19h 50mMultiple Airlines
Thu 12/1111:09 amSWF - STL
3 stops32h 27mMultiple Airlines
Deal found 11/25$450
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/297:43 pmSTL - SWF
2 stops14h 20mMultiple Airlines
Thu 1/111:43 amSWF - STL
1 stop11h 50mMultiple Airlines
Deal found 11/25$475
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 11/26$621

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 26, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$179
(Mytrip)

One-way from

$89
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$217
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
Search Deals
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
Highest demand for flights based on searches. 5% potential increase in price ($11 potential increase over avg. RT price).
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
Search Deals

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 26, 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 1/29

8:22 pm-10:19 am

1 stop12h 57m

New Windsor Stewart

Mon 2/2

11:09 am-11:46 pm

1 stop13h 37m

$179

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/8

8:22 pm-10:19 am

1 stop12h 57m

New Windsor Stewart

Mon 1/12

11:09 am-11:46 pm

1 stop13h 37m

$179

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/22

8:22 pm-10:19 am

1 stop12h 57m

New Windsor Stewart

Mon 1/26

11:09 am-8:54 pm

1 stop10h 45m

$189

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/11

6:15 am-11:37 am

1 stop28h 22m

New Windsor Stewart

Mon 12/15

12:24 pm-9:48 pm

2 stops10h 24m

$237

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 12/7

5:00 am-11:37 am

1 stop29h 37m

New Windsor Stewart

Fri 12/12

12:27 pm-12:09 am

1 stop12h 42m

$238

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:22 pm-10:19 am

1 stop12h 57m

New Windsor Stewart

Mon 1/19

11:09 am-11:46 pm

1 stop13h 37m

$248

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 12/7

5:00 am-11:37 am

1 stop29h 37m

New Windsor Stewart

Mon 12/8

7:30 pm-2:31 pm

2 stops44h 01m

$262

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 12/7

5:00 am-11:37 am

1 stop29h 37m

New Windsor Stewart

Thu 12/11

11:09 am-12:09 am

2 stops14h 00m

$269

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Wed 12/10

3:30 pm-11:03 am

1 stop18h 33m

New Windsor Stewart

Fri 12/12

7:30 pm-10:33 pm

1 stop28h 03m

$273

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Sat 12/6

7:43 pm-11:03 am

2 stops14h 20m

New Windsor Stewart

Mon 12/15

7:30 pm-10:33 pm

1 stop28h 03m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 47 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 $35). 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 29h 02m. Your travel time can differ by up to . The distance between Illinois and New Windsor is about 813 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 Chicago Midway - 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 $35). 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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