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Stewart

$87+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SWF
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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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 October 29, 2025.

This Mytrip deal was found by Cheapflights users on 10/28. 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 12/44:21 pmORD - SWF
1 stop18h 16mMultiple Airlines
Mon 12/812:27 pmSWF - ORD
1 stop8h 34mMultiple Airlines
Deal found 10/28$241
This Mytrip deal was found by Cheapflights users on 10/28. 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 11/68:28 amORD - SWF
2 stops25h 13mMultiple Airlines
Mon 11/1012:01 pmSWF - ORD
1 stop13h 26mMultiple Airlines
Deal found 10/28$292
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/226:02 pmMDW - SWF
1 stop16h 01mMultiple Airlines
Sun 11/236:23 pmSWF - MDW
2 stops23h 29mMultiple Airlines
Deal found 10/27$491

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 October 29, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$241
(Mytrip)

One-way from

$87
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$201
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.
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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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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 29, 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 12/4

4:21 pm-11:37 am

1 stop18h 16m

New Windsor Stewart

Mon 12/8

12:27 pm-8:01 pm

1 stop8h 34m

$241

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/6

8:28 am-10:41 am

2 stops25h 13m

New Windsor Stewart

Mon 11/10

12:01 pm-12:27 am

1 stop13h 26m

$292

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sat 11/22

6:02 pm-11:03 am

1 stop16h 01m

New Windsor Stewart

Sun 11/23

6:23 pm-4:52 pm

2 stops23h 29m

$491

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 12/14

3:20 pm-11:37 am

1 stop19h 17m

$97

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/20

3:26 pm-10:22 am

1 stop17h 56m

$98

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

11:42 am-10:19 am

1 stop21h 37m

$104

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Tue 11/25

11:48 am-11:27 am

1 stop22h 39m

$112

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Mon 11/17

6:06 pm-10:26 am

1 stop15h 20m

$115

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 1/7

6:11 pm-10:19 am

2 stops39h 08m

$126

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 11/23

5:00 am-10:07 am

1 stop28h 07m

$131

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 23 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 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 Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago-New Windsor flight deals on Cheapflights vs. Expedia 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 Expedia the most. Expedia 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, November is the cheapest month in which you can book a flight from Chicago to New Windsor (average of $50). Flying from Chicago to New Windsor in July is currently the most expensive (average of $104). 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, November is the cheapest month in which you can book a flight from Chicago to New Windsor (average of $50). Flying from Chicago to New Windsor in July is currently the most expensive (average of $104). 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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