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Stewart

$104+ 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 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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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 septiembre 11, 2025.

Round-trip from

$212
(Mytrip)

One-way from

$104
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$167
From Illinois to New Windsor Stewart
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One-way flight from Illinois to New Windsor Stewart
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Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 septiembre 11, 2025.

This Mytrip deal was found by Cheapflights users on 9/11. 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.
jue. 11/65:59 pmORD - SWF
1 stop15h 42mMultiple Airlines
lun. 11/1012:01 pmSWF - ORD
1 stop12h 41mMultiple Airlines
Deal found 9/11$212
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
jue. 11/610:49 amORD - SWF
1 stop22h 52mMultiple Airlines
lun. 11/1712:01 pmSWF - ORD
1 stop12h 41mMultiple Airlines
Deal found 9/10$215
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
jue. 11/610:49 amORD - SWF
1 stop22h 52mMultiple Airlines
vie. 11/1411:01 amSWF - ORD
1 stop10h 59mMultiple Airlines
Deal found 9/10$217
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
dom. 11/95:59 pmORD - SWF
1 stop16h 12mMultiple Airlines
vie. 11/1411:01 amSWF - ORD
1 stop10h 59mMultiple Airlines
Deal found 9/9$232
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
dom. 11/910:49 amORD - SWF
1 stop23h 22mMultiple Airlines
lun. 11/1712:01 pmSWF - ORD
1 stop9h 59mMultiple Airlines
Deal found 9/9$235
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
jue. 10/210:35 amSTL - SWF
1 stop23h 46mMultiple Airlines
mar. 10/711:16 amSWF - STL
2 stops47h 46mMultiple Airlines
Deal found 9/10$285
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
jue. 10/210:35 amSTL - SWF
1 stop23h 46mMultiple Airlines
dom. 10/57:11 pmSWF - STL
2 stops20h 53mMultiple Airlines
Deal found 9/10$312
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
dom. 12/1412:20 pmSTL - SWF
1 stop22h 17mMultiple Airlines
jue. 12/1811:43 amSWF - STL
1 stop12h 03mMultiple Airlines
Deal found 9/9$345
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
mar. 11/2512:20 pmSTL - SWF
1 stop22h 07mMultiple Airlines
lun. 12/15:49 pmSWF - STL
2 stops53h 57mMultiple Airlines
Deal found 9/10$484
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
jue. 10/910:57 amSTL - SWF
1 stop22h 54mMultiple Airlines
lun. 10/1312:24 pmSWF - STL
2 stops8h 57mMultiple Airlines
Deal found 9/11$548
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
mié. 12/313:40 pmSTL - SWF
1 stop18h 23mMultiple Airlines
lun. 1/512:24 pmSWF - STL
2 stops11h 22mMultiple Airlines
Deal found 9/9$701
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
mié. 11/264:13 pmSTL - SWF
1 stop17h 50mMultiple Airlines
dom. 11/3011:43 amSWF - STL
1 stop13h 14mMultiple Airlines
Deal found 9/11$795

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 septiembre 11, 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

jue. 11/6

5:59 pm-10:41 am

1 stop15h 42m

New Windsor Stewart

lun. 11/10

12:01 pm-11:42 pm

1 stop12h 41m

$212

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

jue. 11/6

10:49 am-10:41 am

1 stop22h 52m

New Windsor Stewart

lun. 11/17

12:01 pm-11:42 pm

1 stop12h 41m

$215

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

jue. 11/6

10:49 am-10:41 am

1 stop22h 52m

New Windsor Stewart

vie. 11/14

11:01 am-9:00 pm

1 stop10h 59m

$219

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

dom. 11/9

5:59 pm-11:11 am

1 stop16h 12m

New Windsor Stewart

vie. 11/14

11:01 am-9:00 pm

1 stop10h 59m

$232

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

dom. 11/9

10:49 am-11:11 am

1 stop23h 22m

New Windsor Stewart

lun. 11/17

12:01 pm-9:00 pm

1 stop9h 59m

$235

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

jue. 10/2

10:35 am-11:21 am

1 stop23h 46m

New Windsor Stewart

mar. 10/7

11:16 am-10:02 am

2 stops47h 46m

$285

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

jue. 10/2

10:35 am-11:21 am

1 stop23h 46m

New Windsor Stewart

dom. 10/5

7:11 pm-3:04 pm

2 stops20h 53m

$312

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

mar. 11/25

12:20 pm-11:27 am

1 stop22h 07m

New Windsor Stewart

lun. 12/1

5:49 pm-10:46 pm

2 stops53h 57m

$484

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

jue. 10/9

10:57 am-10:51 am

1 stop22h 54m

New Windsor Stewart

lun. 10/13

12:24 pm-8:21 pm

2 stops8h 57m

$548

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

mié. 11/26

4:13 pm-11:03 am

1 stop17h 50m

New Windsor Stewart

dom. 11/30

11:43 am-11:57 pm

1 stop13h 14m

$795

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 40 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 $109). Flying from Illinois to New Windsor in December is currently the most expensive (average of $202). 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.

What is the cheapest time of day to fly from IL to SWF?

Find hourly flight availability from Illinois to Stewart. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to New Windsor as you normally would.

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.

  • 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 Greater Peoria - 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 $109). Flying from Illinois to New Windsor in December is currently the most expensive (average of $202). 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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