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Stewart

$104+ Cheap flights from Chicago (CHI) 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SWF
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Chicago to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Stewart (SWF). 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

$104
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$187
From Chicago (CHI) to New Windsor Stewart
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One-way flight from Chicago (CHI) to New Windsor Stewart
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Highest demand for flights based on searches. 0% potential increase in price ($2 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 Chicago to Stewart

Cheapest flights from Chicago to Stewart
Explore the most affordable flight options available from Chicago to Stewart. 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 9/14. 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 12/117:49 pmORD - SWF
1 stop21h 51mMultiple Airlines
Mon 12/1512:27 pmSWF - ORD
1 stop9h 33mMultiple Airlines
Deal found 9/14$213
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.
Thu 11/65:59 pmORD - SWF
1 stop15h 42mMultiple Airlines
Mon 11/1012:01 pmSWF - ORD
1 stop9h 59mMultiple Airlines
Deal found 9/15$214
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.
Thu 10/26:44 pmORD - SWF
1 stop15h 37mMultiple Airlines
Mon 10/611:01 amSWF - ORD
1 stop13h 44mMultiple Airlines
Deal found 9/15$219
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.
Wed 12/1010:18 amORD - SWF
1 stop23h 45mMultiple Airlines
Thu 12/116:28 pmSWF - ORD
2 stops27h 32mMultiple Airlines
Deal found 9/15$362
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.
Wed 10/15:17 pmORD - SWF
1 stop16h 46mMultiple Airlines
Sun 10/511:43 amSWF - ORD
1 stop10h 50mMultiple Airlines
Deal found 9/16$399
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.
Sat 10/257:43 pmORD - SWF
1 stop14h 20mMultiple Airlines
Mon 10/2712:24 pmSWF - ORD
2 stops10h 09mMultiple Airlines
Deal found 9/15$520
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.
Sat 10/117:43 pmORD - SWF
1 stop14h 20mMultiple Airlines
Fri 10/1712:24 pmSWF - ORD
2 stops10h 09mMultiple Airlines
Deal found 9/15$556
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.
Wed 10/86:58 pmORD - SWF
1 stop15h 05mMultiple Airlines
Fri 10/1712:24 pmSWF - ORD
2 stops10h 09mMultiple Airlines
Deal found 9/15$559
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.
Wed 11/265:30 pmMDW - SWF
1 stop16h 33mMultiple Airlines
Sun 11/308:41 pmSWF - MDW
1 stop21h 11mMultiple Airlines
Deal found 9/16$682
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 11/218:41 pmMDW - SWF
2 stops37h 22mMultiple Airlines
Fri 11/287:28 pmSWF - MDW
1 stop15h 04mMultiple Airlines
Deal found 9/16$817

Cheapflights Fare Finder

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

Fly from

Chicago

Fly to

Stewart

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 12/11

7:49 pm-6:40 pm

1 stop21h 51m

New Windsor Stewart

Mon 12/15

12:27 pm-9:00 pm

1 stop9h 33m

$213

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/6

5:59 pm-10:41 am

1 stop15h 42m

New Windsor Stewart

Mon 11/10

12:01 pm-9:00 pm

1 stop9h 59m

$214

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/2

6:44 pm-11:21 am

1 stop15h 37m

New Windsor Stewart

Mon 10/6

11:01 am-11:45 pm

1 stop13h 44m

$219

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 12/10

10:18 am-11:03 am

1 stop23h 45m

New Windsor Stewart

Thu 12/11

6:28 pm-9:00 pm

2 stops27h 32m

$362

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 10/1

5:17 pm-11:03 am

1 stop16h 46m

New Windsor Stewart

Sun 10/5

11:43 am-9:33 pm

1 stop10h 50m

$399

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 10/25

7:43 pm-11:03 am

1 stop14h 20m

New Windsor Stewart

Mon 10/27

12:24 pm-9:33 pm

2 stops10h 09m

$520

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 10/8

6:58 pm-11:03 am

1 stop15h 05m

New Windsor Stewart

Fri 10/17

12:24 pm-9:33 pm

2 stops10h 09m

$559

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 11/26

5:30 pm-11:03 am

1 stop16h 33m

New Windsor Stewart

Sun 11/30

8:41 pm-2:31 pm

2 stops18h 50m

$762

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 11/21

8:41 pm-11:03 am

2 stops37h 22m

New Windsor Stewart

Fri 11/28

7:28 pm-9:32 am

1 stop15h 04m

$817

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/23

7:43 pm-10:41 am

1 stop13h 58m

$104

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 27 results
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Best time to book a flight from Chicago to Stewart

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

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

Currently, October is the cheapest month in which you can book a flight from Chicago to New Windsor (average of $109). Flying from Chicago 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.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 Chicago?

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

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago 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 Chicago to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Chicago to New Windsor (average of $109). Flying from Chicago 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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Alternative routes for Chicago to Stewart

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