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Stewart

$89+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SWF
Mar 16 — Mar 231
Mon 3/16
Mon 3/23
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 February 14, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/12. 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 3/1111:19 am
MDW
-
SWF
1 stop22h 49m
Multiple Airlines
Fri 3/139:52 am
SWF
-
MDW
1 stop14h 59m
Multiple Airlines
Deal found 2/12$281
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
Sun 3/112:44 pm
ORD
-
SWF
2 stops21h 47m
Multiple Airlines
Thu 3/510:09 am
SWF
-
ORD
1 stop13h 56m
Multiple Airlines
Deal found 2/14$282
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 3/116:36 pm
ORD
-
SWF
1 stop13h 43m
Multiple Airlines
Fri 3/139:52 am
SWF
-
ORD
1 stop14h 46m
Multiple Airlines
Deal found 2/12$292
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 3/78:16 pm
ORD
-
SWF
1 stop11h 03m
Multiple Airlines
Sun 3/87:27 pm
SWF
-
ORD
2 stops16h 29m
Multiple Airlines
Deal found 2/13$334
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 2/1710:44 am
ORD
-
SWF
1 stop29h 12m
Multiple Airlines
Fri 3/612:11 pm
SWF
-
ORD
2 stops12h 27m
Multiple Airlines
Deal found 2/13$396
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 6/177:06 am
ORD
-
SWF
1 stop25h 32m
Multiple Airlines
Sat 6/2012:05 pm
SWF
-
ORD
2 stops20h 49m
Multiple Airlines
Deal found 2/13$438
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 3/159:15 am
ORD
-
SWF
2 stops25h 16m
Multiple Airlines
Sun 3/2210:29 am
SWF
-
ORD
1 stop31h 48m
Multiple Airlines
Deal found 2/13$469
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 4/1112:25 pm
ORD
-
SWF
1 stop21h 30m
Multiple Airlines
Mon 4/1311:40 am
SWF
-
ORD
1 stop12h 56m
Multiple Airlines
Deal found 2/12$497
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 2/164:42 pm
ORD
-
SWF
2 stops18h 09m
Multiple Airlines
Fri 3/611:02 am
SWF
-
ORD
1 stop13h 36m
Multiple Airlines
Deal found 2/13$512
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 6/2111:26 am
ORD
-
SWF
2 stops20h 23m
Multiple Airlines
Thu 6/258:04 pm
SWF
-
ORD
1 stop22h 05m
Multiple Airlines
Deal found 2/11$539
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/132:41 pm
MDW
-
SWF
2 stops43h 58m
Multiple Airlines
Fri 3/209:42 am
SWF
-
MDW
1 stop12h 11m
Multiple Airlines
Deal found 2/10$564

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 February 14, 2026.

Most accurate provider

Ovago
2 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$281
(Kiwi.com)

One-way from

$89
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$221
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. 5% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 14, 2026.
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

MDW - SWF

MDWSWF

Chicago Midway

Wed 3/11

11:19 am-11:08 am

1 stop22h 49m

New Windsor Stewart

Fri 3/13

9:52 am-11:51 pm

1 stop14h 59m

$281

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 3/1

12:44 pm-11:31 am

2 stops21h 47m

New Windsor Stewart

Thu 3/5

10:09 am-11:05 pm

1 stop13h 56m

$282

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 3/11

6:36 pm-9:19 am

1 stop13h 43m

New Windsor Stewart

Fri 3/13

9:52 am-11:38 pm

1 stop14h 46m

$292

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 3/7

8:16 pm-8:19 am

1 stop11h 03m

New Windsor Stewart

Sun 3/8

7:27 pm-10:56 am

2 stops16h 29m

$334

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 6/17

7:06 am-9:38 am

1 stop25h 32m

New Windsor Stewart

Sat 6/20

12:05 pm-7:54 am

2 stops20h 49m

$438

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 3/15

9:15 am-11:31 am

2 stops25h 16m

New Windsor Stewart

Sun 3/22

10:29 am-5:17 pm

1 stop31h 48m

$469

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 4/11

12:25 pm-10:55 am

1 stop21h 30m

New Windsor Stewart

Mon 4/13

11:40 am-11:36 pm

1 stop12h 56m

$497

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 6/21

11:26 am-8:49 am

2 stops20h 23m

New Windsor Stewart

Thu 6/25

8:04 pm-5:09 pm

1 stop22h 05m

$539

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 6/24

5:14 pm-8:58 am

1 stop14h 44m

New Windsor Stewart

Sat 6/27

8:00 pm-7:59 am

1 stop12h 59m

$539

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 3/13

2:41 pm-11:39 am

2 stops43h 58m

New Windsor Stewart

Fri 3/20

9:42 am-8:53 pm

1 stop12h 11m

$564

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 28 results
1
2
3

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy2 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 90-95% 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

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

Currently, January is the cheapest month in which you can book a flight from Chicago to New Windsor (average of $34). Flying from Chicago to New Windsor in July is currently the most expensive (average of $100). 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, January is the cheapest month in which you can book a flight from Chicago to New Windsor (average of $34). Flying from Chicago to New Windsor in July is currently the most expensive (average of $100). 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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