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$107+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CHI
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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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 October 27, 2025.

This Mytrip deal was found by Cheapflights users on 10/23. 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 10/3111:31 amSWF - ORD
1 stop14h 32mMultiple Airlines
Thu 11/68:28 amORD - SWF
2 stops25h 13mMultiple Airlines
Deal found 10/23$252
This Mytrip deal was found by Cheapflights users on 10/25. 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 11/711:31 amSWF - ORD
1 stop13h 56mMultiple Airlines
Thu 11/133:26 pmORD - SWF
1 stop17h 45mMultiple Airlines
Deal found 10/25$272
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/25:11 amORD - SWF
2 stops29h 00mMultiple Airlines
Deal found 10/24$288
This Mytrip deal was found by Cheapflights users on 10/24. 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 12/196:56 pmSWF - ORD
1 stop17h 18mMultiple Airlines
Mon 12/225:00 amORD - SWF
1 stop13h 35mMultiple Airlines
Deal found 10/24$335
This Mytrip deal was found by Cheapflights users on 10/24. 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 11/2111:12 amSWF - ORD
1 stop13h 01mMultiple Airlines
Sat 11/2910:01 amORD - SWF
2 stops22h 21mMultiple Airlines
Deal found 10/24$364
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/911:43 amSWF - ORD
2 stops12h 45mMultiple Airlines
Thu 11/133:26 pmORD - SWF
1 stop17h 45mMultiple Airlines
Deal found 10/25$367
This Mytrip deal was found by Cheapflights users on 10/25. 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 12/196:56 pmSWF - ORD
1 stop17h 18mMultiple Airlines
Sun 12/217:57 pmORD - SWF
2 stops22h 38mMultiple Airlines
Deal found 10/25$373
This Mytrip deal was found by Cheapflights users on 10/25. 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 12/196:56 pmSWF - ORD
1 stop17h 18mMultiple Airlines
Sun 12/2812:09 pmORD - SWF
2 stops21h 38mMultiple Airlines
Deal found 10/25$416
This Mytrip deal was found by Cheapflights users on 10/26. 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 10/306:16 pmSWF - MDW
2 stops25h 00mAllegiant Air
Mon 11/32:45 pmMDW - SWF
2 stops18h 41mAllegiant Air
Deal found 10/26$505

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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(Mytrip)

One-way from

$107
(Mytrip)

Popular in

August

Cheapest in

January

Average price

$242
Provider with most accurate pricing for New Windsor Stewart-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Chicago (CHI) flights.
Search Deals
From New Windsor Stewart to Chicago (CHI)
Search Deals
One-way flight from New Windsor Stewart to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
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 October 2025
Search Deals

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 October 27, 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 1/23

11:09 am-11:42 pm

1 stop13h 33m

Chicago O'Hare Intl

Sun 1/25

5:59 pm-10:19 am

1 stop15h 20m

$229

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/7

11:31 am-12:27 am

1 stop13h 56m

Chicago O'Hare Intl

Thu 11/13

3:26 pm-10:11 am

1 stop17h 45m

$272

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 11/24

10:57 am-9:17 am

1 stop23h 20m

Chicago O'Hare Intl

Thu 11/27

8:45 am-11:44 am

2 stops25h 59m

$334

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 11/9

11:43 am-11:28 pm

2 stops12h 45m

Chicago O'Hare Intl

Thu 11/13

3:26 pm-10:11 am

1 stop17h 45m

$367

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 11/10

12:01 pm-9:47 am

1 stop22h 46m

Chicago O'Hare Intl

Fri 11/14

10:43 pm-11:03 am

2 stops35h 20m

$367

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/19

6:56 pm-11:14 am

1 stop17h 18m

Chicago O'Hare Intl

Sun 12/21

7:57 pm-7:35 pm

2 stops22h 38m

$373

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Mon 1/26

6:02 pm-9:36 am

1 stop16h 34m

Chicago Greater Rockford

Mon 2/2

10:42 am-6:43 pm

1 stop7h 01m

$391

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 12/22

8:25 pm-11:14 am

1 stop15h 49m

Chicago O'Hare Intl

Sun 12/28

12:09 pm-10:47 am

2 stops21h 38m

$416

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/19

6:56 pm-11:14 am

1 stop17h 18m

Chicago O'Hare Intl

Sun 12/28

12:09 pm-10:47 am

2 stops21h 38m

$425

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sun 1/4

11:43 am-9:04 pm

1 stop10h 21m

Chicago Midway

Sun 1/18

2:12 pm-10:19 am

2 stops19h 07m

$757

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/24

Showing 1-10 of 32 results
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Compare providers for flights from Stewart to Chicago

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 Stewart to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 New Windsor-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from New Windsor-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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 New Windsor-Chicago 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 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, November is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $54). Flying from New Windsor to Chicago in July is currently the most expensive (average of $126). 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 $391, Allegiant Air can have you in Chicago from New Windsor in 16h 34m. 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 Greater Rockford or New Windsor Stewart - Chicago Midway, 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, November is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $54). Flying from New Windsor to Chicago in July is currently the most expensive (average of $126). 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
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