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Stewart

$99+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SWF
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
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 agosto 20, 2025.

Round-trip from

$224
(Mytrip)

One-way from

$99
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$218
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. 3% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 20, 2025.

This Mytrip deal was found by Cheapflights users on 8/18. 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.
jue. 10/167:29 pmORD - SWF
1 stop14h 12mMultiple Airlines
lun. 10/2011:01 amSWF - ORD
1 stop8h 23mMultiple Airlines
Deal found 8/18$224
This Mytrip deal was found by Cheapflights users on 8/20. 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.
dom. 11/95:59 pmORD - SWF
1 stop16h 12mMultiple Airlines
vie. 11/1411:01 amSWF - ORD
1 stop13h 41mMultiple Airlines
Deal found 8/20$228
This Mytrip deal was found by Cheapflights users on 8/19. 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.
jue. 10/231:26 pmORD - SWF
2 stops20h 15mMultiple Airlines
lun. 10/273:01 pmSWF - ORD
1 stop11h 02mMultiple Airlines
Deal found 8/19$232
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/26:44 pmORD - SWF
1 stop15h 37mMultiple Airlines
dom. 10/55:45 pmSWF - ORD
2 stops25h 39mMultiple Airlines
Deal found 8/17$358
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
jue. 12/188:30 pmORD - SWF
2 stops20h 36mMultiple Airlines
lun. 1/1911:09 amSWF - ORD
1 stop23h 14mMultiple Airlines
Deal found 8/19$402
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
dom. 8/317:46 pmORD - SWF
1 stop13h 26mMultiple Airlines
lun. 9/11:55 pmSWF - ORD
1 stop21h 36mMultiple Airlines
Deal found 8/19$407
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
jue. 10/97:29 pmORD - SWF
1 stop14h 22mMultiple Airlines
dom. 10/125:45 pmSWF - ORD
2 stops18h 02mMultiple Airlines
Deal found 8/18$424
This Mytrip deal was found by Cheapflights users on 8/19. 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.
dom. 8/2410:12 amORD - SWF
1 stop6h 48mMultiple Airlines
lun. 8/255:36 pmSWF - ORD
1 stop17h 55mMultiple Airlines
Deal found 8/19$457
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
dom. 9/218:49 pmORD - SWF
2 stops13h 55mMultiple Airlines
jue. 9/2511:43 amSWF - ORD
1 stop9h 01mMultiple Airlines
Deal found 8/20$480
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
dom. 8/249:17 amMDW - SWF
1 stop8h 55mMultiple Airlines
jue. 8/287:52 pmSWF - MDW
1 stop13h 30mMultiple Airlines
Deal found 8/18$796

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 agosto 20, 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

jue. 10/23

4:45 pm-10:41 am

1 stop16h 56m

New Windsor Stewart

lun. 10/27

3:01 pm-1:03 am

1 stop11h 02m

$224

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

jue. 10/16

7:29 pm-10:41 am

1 stop14h 12m

New Windsor Stewart

lun. 10/20

11:01 am-6:24 pm

1 stop8h 23m

$224

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

dom. 11/9

5:59 pm-11:11 am

1 stop16h 12m

New Windsor Stewart

vie. 11/14

11:01 am-11:42 pm

1 stop13h 41m

$228

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

jue. 10/2

6:44 pm-11:21 am

1 stop15h 37m

New Windsor Stewart

dom. 10/5

5:45 pm-6:24 pm

2 stops25h 39m

$358

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

jue. 12/18

8:30 pm-6:06 pm

2 stops20h 36m

New Windsor Stewart

lun. 1/19

11:09 am-9:23 am

1 stop23h 14m

$402

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

dom. 8/31

7:46 pm-10:12 am

1 stop13h 26m

New Windsor Stewart

lun. 9/1

1:55 pm-10:31 am

1 stop21h 36m

$407

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

jue. 10/9

7:29 pm-10:51 am

1 stop14h 22m

New Windsor Stewart

dom. 10/12

5:45 pm-10:47 am

2 stops18h 02m

$424

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

dom. 9/21

8:49 pm-11:44 am

2 stops13h 55m

New Windsor Stewart

jue. 9/25

11:43 am-7:44 pm

1 stop9h 01m

$480

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

dom. 8/24

9:17 am-7:12 pm

1 stop8h 55m

New Windsor Stewart

jue. 8/28

7:52 pm-8:22 am

1 stop13h 30m

$796

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

jue. 10/2

6:44 pm-11:21 am

1 stop15h 37m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 23 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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