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Stewart

$88+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Jan 26 — Feb 21
Mon 1/26
Mon 2/2
1 adult, Economy
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Cheap 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 December 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/25. 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 12/2912:22 pmEVV - SWF
1 stop21h 41mMultiple Airlines
Wed 12/315:34 pmSWF - EVV
1 stop24h 28mMultiple Airlines
Deal found 12/25$705
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Tue 12/309:43 amMDW - SWF
1 stop23h 07mMultiple Airlines
Fri 1/212:24 pmSWF - MDW
2 stops10h 34mMultiple Airlines
Deal found 12/25$759
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Mon 12/294:27 pmSTL - SWF
1 stop17h 36mMultiple Airlines
Thu 1/111:43 amSWF - STL
1 stop11h 50mMultiple Airlines
Deal found 12/26$770
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Sun 12/288:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Thu 1/812:13 pmSWF - ORD
1 stop8h 28mMultiple Airlines
Deal found 12/25$812
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 12/2912:22 pmEVV - SWF
1 stop21h 41mMultiple Airlines
Fri 1/28:18 pmSWF - EVV
1 stop12h 51mMultiple Airlines
Deal found 12/25$827
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Thu 12/2511:51 amSTL - SWF
1 stop22h 16mMultiple Airlines
Tue 12/3011:43 amSWF - STL
1 stop11h 50mMultiple Airlines
Deal found 12/25$886
This Kiwi.com deal was found by Cheapflights users on 12/24. 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 12/2811:51 amSTL - SWF
1 stop21h 56mMultiple Airlines
Tue 12/3011:43 amSWF - STL
1 stop11h 50mMultiple Airlines
Deal found 12/24$932
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Sun 12/288:09 pmORD - SWF
1 stop14h 53mMultiple Airlines
Sun 1/411:43 amSWF - ORD
1 stop8h 16mMultiple Airlines
Deal found 12/25$937
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Sat 12/272:16 pmMDW - SWF
1 stop19h 47mMultiple Airlines
Thu 1/111:43 amSWF - MDW
1 stop11h 15mMultiple Airlines
Deal found 12/26$1,059
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Sun 12/288:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Tue 12/3011:43 amSWF - ORD
1 stop8h 19mMultiple Airlines
Deal found 12/25$1,134
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/288:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Thu 1/111:43 amSWF - ORD
1 stop8h 19mMultiple Airlines
Deal found 12/26$1,267

Find flight deals from Illinois to Stewart

Keep the following information in mind while searching for Illinois to Stewart flight deals. Data was last updated December 27, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$209
(Kiwi.com)

One-way from

$88
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$236
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
Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 27, 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

Sun 1/25

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Sun 2/1

12:13 pm-10:41 am

1 stop23h 28m

$209

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/8

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Mon 1/12

11:09 am-7:38 pm

1 stop9h 29m

$252

PeoriaNew Windsor

PIA - SWF

PIASWF

Greater Peoria

Thu 4/2

5:05 pm-9:10 am

1 stop15h 05m

New Windsor Stewart

Mon 4/6

7:50 pm-12:51 pm

1 stop18h 01m

$534

PeoriaNew Windsor

PIA - SWF

PIASWF

Greater Peoria

Fri 4/3

5:04 pm-9:27 am

1 stop15h 23m

New Windsor Stewart

Mon 4/6

7:50 pm-12:51 pm

1 stop18h 01m

$592

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 1/4

8:09 pm-11:44 am

2 stops14h 35m

New Windsor Stewart

Thu 1/8

12:13 pm-7:41 pm

1 stop8h 28m

$660

EvansvilleNew Windsor

EVV - SWF

EVVSWF

Evansville Dress Regional

Mon 12/29

12:22 pm-11:03 am

1 stop21h 41m

New Windsor Stewart

Wed 12/31

5:34 pm-5:02 pm

1 stop24h 28m

$705

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Tue 12/30

9:43 am-9:50 am

1 stop23h 07m

New Windsor Stewart

Fri 1/2

12:24 pm-9:58 pm

2 stops10h 34m

$759

St. LouisNew Windsor

STL - SWF

STLSWF

Lambert-St Louis

Mon 12/29

4:27 pm-11:03 am

1 stop17h 36m

New Windsor Stewart

Thu 1/1

11:43 am-10:33 pm

1 stop11h 50m

$770

EvansvilleNew Windsor

EVV - SWF

EVVSWF

Evansville Dress Regional

Mon 12/29

12:22 pm-11:03 am

1 stop21h 41m

New Windsor Stewart

Fri 1/2

8:18 pm-8:09 am

1 stop12h 51m

$827

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 1/25

3:05 pm-10:19 am

1 stop18h 14m

$88

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 38 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 15h 05m. 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, Moline Quad-City - New Windsor Stewart or Lambert-St Louis - 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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