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Stewart

$98+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Nov 12 — Nov 191
Wed 11/12
Wed 11/19
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 October 13, 2025.

This Mytrip deal was found by Cheapflights users on 10/10. 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 10/275:05 amORD - SWF
1 stop8h 06mMultiple Airlines
Fri 10/3111:31 amSWF - ORD
1 stop14h 32mMultiple Airlines
Deal found 10/10$187
This Mytrip deal was found by Cheapflights users on 10/11. 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 11/203:26 pmORD - SWF
1 stop17h 56mMultiple Airlines
Mon 11/2410:57 amSWF - ORD
1 stop10h 30mMultiple Airlines
Deal found 10/11$223
This Mytrip deal was found by Cheapflights users on 10/12. 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 10/234:59 pmORD - SWF
1 stop16h 42mMultiple Airlines
Mon 10/273:01 pmSWF - ORD
1 stop11h 02mMultiple Airlines
Deal found 10/12$224
This Mytrip deal was found by Cheapflights users on 10/11. 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 11/233:26 pmORD - SWF
1 stop17h 41mMultiple Airlines
Wed 11/2612:17 pmSWF - ORD
1 stop11h 56mMultiple Airlines
Deal found 10/11$257
This Mytrip deal was found by Cheapflights users on 10/12. 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 10/278:20 amPIA - SWF
1 stop9h 56mAllegiant Air
Fri 10/318:06 pmSWF - PIA
1 stop15h 24mAllegiant Air
Deal found 10/12$331
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 10/249:54 pmORD - SWF
2 stops36h 09mMultiple Airlines
Mon 10/273:01 pmSWF - ORD
1 stop11h 02mMultiple Airlines
Deal found 10/11$333
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/175:11 pmSTL - SWF
1 stop16h 52mMultiple Airlines
Sun 1/1111:48 amSWF - STL
1 stop11h 45mMultiple Airlines
Deal found 10/11$354
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/111:36 amMDW - SWF
1 stop23h 27mMultiple Airlines
Tue 11/411:16 amSWF - MDW
2 stops26h 25mMultiple Airlines
Deal found 10/12$357
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 12/135:11 pmSTL - SWF
1 stop16h 52mMultiple Airlines
Mon 12/1512:24 pmSWF - STL
2 stops11h 22mMultiple Airlines
Deal found 10/10$369
This Mytrip deal was found by Cheapflights users on 10/11. 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 10/161:26 pmORD - SWF
2 stops20h 15mMultiple Airlines
Mon 10/2011:01 amSWF - ORD
1 stop13h 44mMultiple Airlines
Deal found 10/11$422
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 11/264:13 pmSTL - SWF
1 stop17h 50mMultiple Airlines
Sun 11/308:41 pmSWF - STL
1 stop28h 16mMultiple Airlines
Deal found 10/10$424
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/259:06 amMLI - SWF
2 stops25h 21mMultiple Airlines
Sun 11/308:41 pmSWF - MLI
1 stop12h 05mMultiple Airlines
Deal found 10/12$453

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 October 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$187
(Mytrip)

One-way from

$98
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$201
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, 1% potential price rise
Search Deals
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 October 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 October 13, 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

Mon 10/27

5:05 am-2:11 pm

1 stop8h 06m

New Windsor Stewart

Fri 10/31

11:31 am-1:03 am

1 stop14h 32m

$187

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/20

3:26 pm-10:22 am

1 stop17h 56m

New Windsor Stewart

Mon 11/24

10:57 am-8:27 pm

1 stop10h 30m

$223

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/23

7:43 pm-10:41 am

1 stop13h 58m

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

Sun 11/23

3:26 pm-10:07 am

1 stop17h 41m

New Windsor Stewart

Wed 11/26

12:17 pm-11:13 pm

1 stop11h 56m

$257

PeoriaNew Windsor

PIA - SWF

PIASWF

Greater Peoria

Mon 10/27

8:20 am-7:16 pm

1 stop9h 56m

New Windsor Stewart

Fri 10/31

8:06 pm-10:30 am

1 stop15h 24m

$331

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 10/24

9:54 pm-11:03 am

2 stops36h 09m

New Windsor Stewart

Mon 10/27

3:01 pm-1:03 am

1 stop11h 02m

$333

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Wed 12/17

5:11 pm-11:03 am

1 stop16h 52m

New Windsor Stewart

Sun 1/11

11:48 am-10:33 pm

1 stop11h 45m

$354

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sat 11/1

11:36 am-12:03 pm

1 stop23h 27m

New Windsor Stewart

Tue 11/4

11:16 am-12:41 pm

2 stops26h 25m

$357

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Sat 12/13

5:11 pm-11:03 am

1 stop16h 52m

New Windsor Stewart

Mon 12/15

12:24 pm-10:46 pm

2 stops11h 22m

$369

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Wed 11/26

4:13 pm-11:03 am

1 stop17h 50m

New Windsor Stewart

Sun 11/30

8:41 pm-11:57 pm

1 stop28h 16m

$424

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 51 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 $54). 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 9h 56m. 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, October is the cheapest month in which you can book a flight from Illinois to New Windsor (average of $54). 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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