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$89+ Cheap flights from New Windsor (SWF) to Illinois

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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORD
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap flight deals from Stewart to Illinois

Keep the following information in mind while searching for Stewart to Illinois flight deals. Data was last updated January 8, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$182
(Mytrip)

One-way from

$89
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$179
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
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From New Windsor Stewart to Illinois
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One-way flight from New Windsor Stewart to Illinois
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Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Stewart to Illinois

Cheapest flights from Stewart to Illinois
Explore the most affordable flight options available from Stewart to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 8, 2026.

This Mytrip deal was found by Cheapflights users on 1/6. 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.
Fri 1/3011:09 amSWF - ORD
1 stop9h 29mMultiple Airlines
Sun 2/18:43 pmORD - SWF
1 stop12h 36mMultiple Airlines
Deal found 1/6$182
This Mytrip deal was found by Cheapflights users on 1/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/211:09 amSWF - ORD
1 stop13h 38mMultiple Airlines
Thu 2/58:43 pmORD - SWF
1 stop12h 36mMultiple Airlines
Deal found 1/5$196
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Thu 1/2912:13 pmSWF - STL
1 stop12h 20mMultiple Airlines
Sun 2/15:42 pmSTL - SWF
1 stop24h 01mMultiple Airlines
Deal found 1/6$197
This Mytrip deal was found by Cheapflights users on 1/6. 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.
Fri 2/611:09 amSWF - ORD
1 stop9h 29mMultiple Airlines
Sun 2/88:43 pmORD - SWF
1 stop12h 36mMultiple Airlines
Deal found 1/6$204
This Mytrip deal was found by Cheapflights users on 1/6. 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.
Fri 1/2311:09 amSWF - ORD
1 stop10h 54mMultiple Airlines
Sun 1/258:43 pmORD - SWF
1 stop12h 36mMultiple Airlines
Deal found 1/6$230
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/1912:11 pmSWF - ORD
2 stops26h 02mMultiple Airlines
Sun 1/253:05 pmORD - SWF
1 stop18h 14mMultiple Airlines
Deal found 1/6$261
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Thu 2/511:48 amSWF - MDW
1 stop9h 04mMultiple Airlines
Thu 2/123:00 pmMDW - SWF
2 stops50h 39mMultiple Airlines
Deal found 1/6$301
This Mytrip deal was found by Cheapflights users on 1/7. 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 1/266:02 pmSWF - RFD
1 stop16h 34mAllegiant Air
Fri 1/3010:42 amRFD - SWF
1 stop7h 01mAllegiant Air
Deal found 1/7$373
This Mytrip deal was found by Cheapflights users on 1/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/26:02 pmSWF - RFD
1 stop16h 34mMultiple Airlines
Thu 2/51:24 pmRFD - SWF
2 stops19h 55mMultiple Airlines
Deal found 1/5$588
This Kiwi.com deal was found by Cheapflights users on 1/8. 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 1/1512:13 pmSWF - STL
1 stop11h 21mMultiple Airlines
Sun 1/185:11 pmSTL - SWF
1 stop24h 32mMultiple Airlines
Deal found 1/8$597
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 3/1211:48 amSWF - STL
1 stop12h 31mMultiple Airlines
Sat 3/148:53 pmSTL - SWF
1 stop13h 15mMultiple Airlines
Deal found 1/7$601
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 3/2012:11 pmSWF - STL
2 stops12h 08mMultiple Airlines
Sat 3/218:53 pmSTL - SWF
1 stop13h 15mMultiple Airlines
Deal found 1/7$920

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Illinois 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 January 8, 2026.
Use the filters below to find and compare flights from New Windsor to Illinois that are best for you.

Fly from

Stewart

Fly to

Illinois

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/30

11:09 am-7:38 pm

1 stop9h 29m

Chicago O'Hare Intl

Sun 2/1

8:43 pm-10:19 am

1 stop12h 36m

$182

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 2/2

11:09 am-11:47 pm

1 stop13h 38m

Chicago O'Hare Intl

Thu 2/5

8:43 pm-10:19 am

1 stop12h 36m

$196

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Thu 1/29

12:13 pm-11:33 pm

1 stop12h 20m

Lambert-St Louis

Sun 2/1

5:42 pm-6:43 pm

1 stop24h 01m

$197

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 2/6

11:09 am-7:38 pm

1 stop9h 29m

Chicago O'Hare Intl

Sun 2/8

8:43 pm-10:19 am

1 stop12h 36m

$204

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/23

11:09 am-9:03 pm

1 stop10h 54m

Chicago O'Hare Intl

Sun 1/25

8:43 pm-10:19 am

1 stop12h 36m

$230

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 2/5

11:48 am-7:52 pm

1 stop9h 04m

Chicago Midway

Thu 2/12

3:00 pm-6:39 pm

2 stops50h 39m

$301

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Mon 1/26

6:02 pm-9:36 am

1 stop16h 34m

Chicago Greater Rockford

Fri 1/30

10:42 am-6:43 pm

1 stop7h 01m

$373

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Mon 2/2

6:02 pm-9:36 am

1 stop16h 34m

Chicago Greater Rockford

Thu 2/5

1:24 pm-10:19 am

2 stops19h 55m

$588

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Thu 3/12

11:48 am-11:19 pm

1 stop12h 31m

Lambert-St Louis

Sat 3/14

8:53 pm-11:08 am

1 stop13h 15m

$601

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Fri 3/20

12:11 pm-11:19 pm

2 stops12h 08m

Lambert-St Louis

Sat 3/21

8:53 pm-11:08 am

1 stop13h 15m

$920

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 40 results
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Best time to book a flight from Stewart to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Stewart 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 New Windsor to Illinois

What is the cheapest month to book a flight from New Windsor to Illinois?

Currently, December is the cheapest month in which you can book a flight from New Windsor to Illinois (average of $48). Flying from New Windsor to Illinois in July is currently the most expensive (average of $126). 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 Stewart to Illinois. 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 from for flights from New Windsor to Illinois?

    Most people fly from New Windsor Stewart (SWF) if they book a flight from New Windsor to Illinois. New Windsor Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

  • How long is the flight from New Windsor to Illinois?

    Allegiant Air can get you from New Windsor to Illinois in just under 16h 34m. Your travel time can differ by up to . The distance from New Windsor to Illinois is about 772 mi.

  • What are the most popular routes from New Windsor to Illinois?

    While some choose either New Windsor Stewart - Lambert-St Louis or New Windsor Stewart - Evansville Dress Regional, New Windsor Stewart - Chicago O'Hare Intl is the most popular route from New Windsor to Illinois.

  • Can I find deals for flights from Stewart to Illinois that include hotel bookings?

    Yes. In addition to deals on Stewart to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Illinois.

  • Can I find deals for business class flights from Stewart to Illinois?

    Yes. Cheapflights offers flight deals from Stewart to Illinois 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 New Windsor to Illinois?

    Currently, December is the cheapest month in which you can book a flight from New Windsor to Illinois (average of $48). Flying from New Windsor to Illinois in July is currently the most expensive (average of $126). 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

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