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$102+ Cheap flights from New Windsor (SWF) to Chicago (CHI)

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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Stewart to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2025.

Round-trip from

$213
(Kiwi.com)

One-way from

$102
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$213
From New Windsor Stewart to Chicago (CHI)
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One-way flight from New Windsor Stewart to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($17 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 September 2025
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Find flight deals from Stewart to Chicago

Cheapest flights from Stewart to Chicago
Explore the most affordable flight options available from Stewart to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/3111:31 amSWF - ORD
1 stop14h 32mMultiple Airlines
Sun 11/27:43 pmORD - SWF
1 stop14h 28mMultiple Airlines
Deal found 9/16$213
This Mytrip deal was found by Cheapflights users on 9/16. 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 stop8h 07mMultiple Airlines
Mon 10/275:05 amORD - SWF
1 stop8h 06mMultiple Airlines
Deal found 9/16$224
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2011:01 amSWF - ORD
1 stop8h 37mMultiple Airlines
Thu 10/237:43 pmORD - SWF
1 stop13h 58mMultiple Airlines
Deal found 9/16$226
This Mytrip deal was found by Cheapflights users on 9/15. 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 10/312:11 pmSWF - ORD
1 stop11h 37mMultiple Airlines
Sun 10/57:43 pmORD - SWF
1 stop13h 28mMultiple Airlines
Deal found 9/15$228
This Mytrip deal was found by Cheapflights users on 9/17. 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 10/1011:41 amSWF - ORD
1 stop7h 57mMultiple Airlines
Sun 10/197:43 pmORD - SWF
1 stop13h 28mMultiple Airlines
Deal found 9/17$250
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/2011:01 amSWF - ORD
1 stop13h 44mMultiple Airlines
Fri 10/249:54 pmORD - SWF
2 stops36h 09mMultiple Airlines
Deal found 9/15$289
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/1611:43 amSWF - ORD
1 stop20h 51mMultiple Airlines
Mon 10/275:05 amORD - SWF
1 stop8h 06mMultiple Airlines
Deal found 9/15$297
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/27:11 pmSWF - MDW
1 stop18h 33mMultiple Airlines
Sun 10/56:21 amMDW - SWF
1 stop11h 00mMultiple Airlines
Deal found 9/16$328
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/1411:16 amSWF - ORD
1 stop23h 52mMultiple Airlines
Tue 10/217:43 pmORD - SWF
2 stops38h 20mMultiple Airlines
Deal found 9/16$344
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/167:11 pmSWF - RFD
1 stop13h 53mAllegiant Air
Mon 10/278:44 amRFD - SWF
1 stop24h 42mAllegiant Air
Deal found 9/15$417
This Mytrip deal was found by Cheapflights users on 9/16. 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 10/27:11 pmSWF - MDW
2 stops22h 23mAllegiant Air
Mon 10/612:08 pmMDW - SWF
2 stops21h 18mAllegiant Air
Deal found 9/16$477
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/234:50 pmSWF - RFD
1 stop24h 59mAllegiant Air
Tue 12/307:54 pmRFD - SWF
1 stop19h 50mAllegiant Air
Deal found 9/16$553

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Chicago 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 September 17, 2025.
Use the filters below to find and compare flights from New Windsor to Chicago that are best for you.

Fly from

Stewart

Fly to

Chicago

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/31

11:31 am-1:03 am

1 stop14h 32m

Chicago O'Hare Intl

Sun 11/2

7:43 pm-11:11 am

1 stop14h 28m

$223

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

$224

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 10/20

11:01 am-6:38 pm

1 stop8h 37m

Chicago O'Hare Intl

Thu 10/23

7:43 pm-10:41 am

1 stop13h 58m

$226

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/10

11:41 am-6:38 pm

1 stop7h 57m

Chicago O'Hare Intl

Sun 10/19

7:43 pm-10:11 am

1 stop13h 28m

$250

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 10/20

11:01 am-11:45 pm

1 stop13h 44m

Chicago O'Hare Intl

Fri 10/24

9:54 pm-11:03 am

2 stops36h 09m

$289

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 10/16

11:43 am-7:34 am

1 stop20h 51m

Chicago O'Hare Intl

Mon 10/27

5:05 am-2:11 pm

1 stop8h 06m

$297

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 10/2

7:11 pm-12:44 pm

1 stop18h 33m

Chicago Midway

Sun 10/5

6:21 am-6:21 pm

1 stop11h 00m

$328

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Tue 10/14

11:16 am-10:08 am

1 stop23h 52m

Chicago O'Hare Intl

Tue 10/21

7:43 pm-11:03 am

2 stops38h 20m

$344

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 10/16

7:11 pm-8:04 am

1 stop13h 53m

Chicago Greater Rockford

Mon 10/27

8:44 am-10:26 am

1 stop24h 42m

$417

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 10/13

11:01 am-11:45 pm

1 stop13h 44m

Chicago O'Hare Intl

Fri 10/17

9:54 pm-11:03 am

2 stops36h 09m

$430

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 37 results
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Best time to book a flight from Stewart to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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 Chicago

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

Currently, August is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $245). Flying from New Windsor to Chicago in March is currently the most expensive (average of $321). 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 Chicago. 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 Chicago?

    Located just 4.3 mi from the city center, New Windsor Stewart is the airport most travelers will use when flying to Chicago from New Windsor. Booking flights from Stewart (SWF) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 0 different airlines.

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

    For as low as $417, Allegiant Air can have you in Chicago from New Windsor in 13h 53m. Airlines will cover a distance of 772 mi.

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

    While some choose either New Windsor Stewart - Chicago Midway or New Windsor Stewart - Chicago Greater Rockford, New Windsor Stewart - Chicago O'Hare Intl is the most popular route from New Windsor to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Chicago 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 Chicago?

    Currently, August is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $245). Flying from New Windsor to Chicago in March is currently the most expensive (average of $321). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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See prices for flight routes from nearby airports that may be better suited for you.
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