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Stewart

$108+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SWF
Aug 9 — Aug 161
Sun 8/9
Sun 8/16
1 adult, Economy
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Cheap 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 July 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/7. 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 8/278:05 am
ORD
-
SWF
1 stop9h 36m
Multiple Airlines
Sun 8/307:31 pm
SWF
-
ORD
1 stop18h 19m
Multiple Airlines
Deal found 7/7$243
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 10/284:44 pm
ORD
-
SWF
1 stop16h 32m
Multiple Airlines
Sun 11/111:58 am
SWF
-
ORD
1 stop28h 26m
Multiple Airlines
Deal found 7/9$292
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Sat 9/264:49 pm
ORD
-
SWF
1 stop16h 27m
Multiple Airlines
Fri 10/28:48 pm
SWF
-
ORD
2 stops16h 14m
Multiple Airlines
Deal found 7/8$298
This Kiwi.com deal was found by Cheapflights users on 7/7. 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.
Sat 8/11:50 pm
ORD
-
SWF
2 stops18h 48m
Multiple Airlines
Thu 8/1310:28 am
SWF
-
ORD
1 stop26h 47m
Multiple Airlines
Deal found 7/7$299
This Kiwi.com deal was found by Cheapflights users on 7/5. 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.
Wed 9/302:03 pm
ORD
-
SWF
2 stops18h 35m
Multiple Airlines
Sun 10/411:48 am
SWF
-
ORD
1 stop28h 38m
Multiple Airlines
Deal found 7/5$301
This Kiwi.com deal was found by Cheapflights users on 7/6. 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.
Wed 8/58:05 am
ORD
-
SWF
1 stop24h 33m
Multiple Airlines
Thu 8/201:00 pm
SWF
-
ORD
1 stop24h 50m
Multiple Airlines
Deal found 7/6$307
This Kiwi.com deal was found by Cheapflights users on 7/5. 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.
Wed 8/198:05 am
ORD
-
SWF
1 stop27h 05m
Multiple Airlines
Wed 8/2612:05 pm
SWF
-
ORD
2 stops12h 03m
Multiple Airlines
Deal found 7/5$337
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/295:59 pm
ORD
-
SWF
1 stop14h 54m
Multiple Airlines
Sun 8/307:31 pm
SWF
-
ORD
1 stop18h 19m
Multiple Airlines
Deal found 7/9$344
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 12/66:10 pm
MDW
-
SWF
1 stop13h 42m
Multiple Airlines
Sun 12/139:36 am
SWF
-
MDW
1 stop10h 26m
Multiple Airlines
Deal found 7/8$427
This Kiwi.com deal was found by Cheapflights users on 7/7. 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 12/244:53 pm
MDW
-
SWF
1 stop15h 57m
Allegiant Air
Mon 12/2811:40 am
SWF
-
MDW
1 stop22h 12m
Allegiant Air
Deal found 7/7$832

Find 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 July 10, 2026.

Most accurate provider

Ovago
3 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$243
(Kiwi.com)

One-way from

$108
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$259
Provider with most accurate pricing for Chicago (CHI)-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-New Windsor Stewart flights.
Search Deals
From Chicago (CHI) to New Windsor Stewart
Search Deals
One-way flight from Chicago (CHI) to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 10, 2026.
Use the filters below to find and compare flights from Chicago to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 8/27

8:05 am-6:41 pm

1 stop9h 36m

New Windsor Stewart

Sun 8/30

7:31 pm-12:50 pm

1 stop18h 19m

$256

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 10/28

4:44 pm-10:16 am

1 stop16h 32m

New Windsor Stewart

Sun 11/1

11:58 am-3:24 pm

1 stop28h 26m

$292

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 8/1

7:05 am-9:38 am

2 stops25h 33m

New Windsor Stewart

Thu 8/13

10:28 am-12:15 pm

1 stop26h 47m

$302

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 8/19

8:05 am-12:10 pm

1 stop27h 05m

New Windsor Stewart

Wed 8/26

12:05 pm-11:08 pm

2 stops12h 03m

$337

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 8/5

1:50 pm-9:38 am

2 stops18h 48m

New Windsor Stewart

Thu 8/20

1:00 pm-12:50 pm

1 stop24h 50m

$349

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 8/28

9:10 pm-11:25 am

2 stops13h 15m

New Windsor Stewart

Sun 8/30

7:31 pm-12:50 pm

1 stop18h 19m

$397
Quickest round-trip

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sun 12/6

6:10 pm-8:52 am

1 stop13h 42m

New Windsor Stewart

Sun 12/13

9:36 am-7:02 pm

1 stop10h 26m

$427

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 8/14

1:50 pm-11:25 am

2 stops20h 35m

New Windsor Stewart

Sun 8/16

10:33 am-11:10 pm

1 stop13h 37m

$537

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Mon 8/31

9:10 pm-11:08 am

1 stop12h 58m

New Windsor Stewart

Sun 9/6

10:33 am-11:08 pm

1 stop13h 35m

$547

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 7/25

1:50 pm-9:53 am

2 stops19h 03m

New Windsor Stewart

Tue 7/28

11:48 am-11:10 pm

1 stop12h 22m

$555

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/6

Showing 1-10 of 31 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Stewart

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Stewart in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-New Windsor flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago-New Windsor flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-New Windsor flights, Cheapflights users trust Ovago the most. Ovago has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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
No data available for this route at this time. Please check back soon.

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.

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

    A quick flight from Chicago to New Windsor can take about 15h 57m. Allegiant Air provides one of the quickest options available for as low as $832. Chicago and New Windsor are separated by a distance of 704 mi.

  • 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.

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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