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$85+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORD
Nov 7 — Nov 141
Fri 11/7
Fri 11/14
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 October 8, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$204
(Mytrip)

One-way from

$85
(Mytrip)

Popular in

August

Cheapest in

January

Average price

$238
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. 7% potential increase in price ($19 potential increase over avg. RT price).
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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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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 October 8, 2025.

This Mytrip deal was found by Cheapflights users on 10/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:31 amSWF - ORD
1 stop13h 14mMultiple Airlines
Mon 10/275:05 amORD - SWF
1 stop8h 06mMultiple Airlines
Deal found 10/8$204
This Mytrip deal was found by Cheapflights users on 10/6. 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 10/2411:31 amSWF - ORD
1 stop13h 14mMultiple Airlines
Sun 10/267:43 pmORD - SWF
1 stop17h 28mMultiple Airlines
Deal found 10/6$212
This Mytrip deal was found by Cheapflights users on 10/7. 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.
Fri 12/512:27 pmSWF - ORD
1 stop12h 15mMultiple Airlines
Sun 12/75:59 pmORD - SWF
1 stop16h 38mMultiple Airlines
Deal found 10/7$221
This Mytrip deal was found by Cheapflights users on 10/7. 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 10/2011:01 amSWF - ORD
1 stop13h 44mMultiple Airlines
Thu 10/234:59 pmORD - SWF
1 stop16h 42mMultiple Airlines
Deal found 10/7$231
This Mytrip deal was found by Cheapflights users on 10/7. 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.
Wed 11/2612:17 pmSWF - ORD
1 stop11h 56mMultiple Airlines
Sun 12/75:59 pmORD - SWF
1 stop16h 38mMultiple Airlines
Deal found 10/7$249
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Tue 10/2811:16 amSWF - MLI
1 stop21h 44mAllegiant Air
Mon 11/311:10 amMLI - SWF
1 stop7h 06mAllegiant Air
Deal found 10/7$282
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3011:43 amSWF - MDW
1 stop21h 49mMultiple Airlines
Mon 11/32:45 pmMDW - SWF
2 stops18h 41mMultiple Airlines
Deal found 10/5$366
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 12/1811:43 amSWF - STL
1 stop12h 03mMultiple Airlines
Sat 1/105:11 pmSTL - SWF
1 stop16h 57mMultiple Airlines
Deal found 10/6$406
This Mytrip deal was found by Cheapflights users on 10/5. 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.
Thu 10/306:16 pmSWF - MDW
2 stops25h 00mAllegiant Air
Mon 11/32:45 pmMDW - SWF
2 stops18h 41mAllegiant Air
Deal found 10/5$437
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Sun 11/308:41 pmSWF - MLI
1 stop12h 05mAllegiant Air
Sat 12/611:32 amMLI - SWF
1 stop21h 47mAllegiant Air
Deal found 10/8$442
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 12/198:11 pmSWF - RFD
1 stop12h 57mAllegiant Air
Mon 12/2210:18 amRFD - SWF
1 stop7h 02mAllegiant Air
Deal found 10/7$478
This Kiwi.com deal was found by Cheapflights users on 10/6. 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.
Fri 12/196:56 pmSWF - STL
1 stop19h 57mMultiple Airlines
Sat 1/105:11 pmSTL - SWF
1 stop16h 57mMultiple Airlines
Deal found 10/6$531

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 October 8, 2025.
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 10/24

11:31 am-6:38 pm

1 stop8h 07m

Chicago O'Hare Intl

Mon 10/27

5:05 am-2:11 pm

1 stop8h 06m

$204

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/24

11:31 am-11:45 pm

1 stop13h 14m

Chicago O'Hare Intl

Sun 10/26

7:43 pm-2:11 pm

1 stop17h 28m

$212

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/5

12:27 pm-11:42 pm

1 stop12h 15m

Chicago O'Hare Intl

Sun 12/7

5:59 pm-11:37 am

1 stop16h 38m

$212

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 10/20

11:01 am-11:45 pm

1 stop13h 44m

Chicago O'Hare Intl

Thu 10/23

4:59 pm-10:41 am

1 stop16h 42m

$231

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 10/30

11:43 am-8:32 am

1 stop21h 49m

Chicago Midway

Mon 11/3

2:45 pm-10:26 am

2 stops18h 41m

$366

New WindsorSt. Louis

SWF - STL

SWFSTL

New Windsor Stewart

Thu 12/18

11:43 am-10:46 pm

1 stop12h 03m

Lambert-St Louis

Sat 1/10

5:11 pm-11:08 am

1 stop16h 57m

$406

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 10/30

6:16 pm-6:16 pm

2 stops25h 00m

Chicago Midway

Mon 11/3

2:45 pm-10:26 am

2 stops18h 41m

$437

New WindsorMoline

SWF - MLI

SWFMLI

New Windsor Stewart

Sun 11/30

8:41 pm-7:46 am

1 stop12h 05m

Moline Quad-City

Sat 12/6

11:32 am-10:19 am

1 stop21h 47m

$442

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Fri 12/19

8:11 pm-8:08 am

1 stop12h 57m

Chicago Greater Rockford

Mon 12/22

10:18 am-6:20 pm

1 stop7h 02m

$462

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 1/15

11:48 am-8:45 pm

1 stop9h 57m

Chicago Midway

Sun 1/18

9:43 pm-11:31 am

2 stops12h 48m

$589

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/8

Showing 1-10 of 51 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, May is the cheapest month in which you can book a flight from New Windsor to Illinois (average of $55). 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 25h. Your travel time can differ by up to . The distance from New Windsor to Illinois is about 704 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 - Moline Quad-City, 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, May is the cheapest month in which you can book a flight from New Windsor to Illinois (average of $55). 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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