HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$97+ 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
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 18, 2025.

Round-trip from

$211
(Kiwi.com)

One-way from

$97
(Mytrip)

Popular in

June

Cheapest in

September

Average price

$269
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. 11% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/257:12 pmSWF - MDW
1 stop18h 32mMultiple Airlines
Sun 9/286:21 amMDW - SWF
1 stop11h 01mMultiple Airlines
Deal found 8/16$211
This Mytrip 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 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
Sun 11/27:29 pmORD - SWF
1 stop14h 42mMultiple Airlines
Deal found 8/17$219
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1711:31 amSWF - ORD
1 stop13h 14mMultiple Airlines
Sun 10/194:45 pmORD - SWF
1 stop16h 26mMultiple Airlines
Deal found 8/17$244
This Mytrip deal was found by Cheapflights users on 8/16. 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.
Mon 10/611:01 amSWF - ORD
1 stop13h 44mMultiple Airlines
Thu 10/94:45 pmORD - SWF
1 stop17h 06mMultiple Airlines
Deal found 8/16$245
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/2211:53 amSWF - RFD
1 stop22h 37mAllegiant Air
Thu 9/2511:00 amRFD - SWF
1 stop23h 03mAllegiant Air
Deal found 8/16$253
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/187:12 pmSWF - RFD
1 stop13h 48mAllegiant Air
Thu 9/2511:00 amRFD - SWF
1 stop23h 03mAllegiant Air
Deal found 8/16$267
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1011:41 amSWF - ORD
1 stop13h 04mMultiple Airlines
Sun 10/121:26 pmORD - SWF
2 stops19h 45mMultiple Airlines
Deal found 8/17$269
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 9/187:12 pmSWF - MDW
1 stop18h 32mMultiple Airlines
Sun 9/216:21 amMDW - SWF
1 stop11h 01mMultiple Airlines
Deal found 8/15$274
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 8/302:32 pmSWF - ORD
1 stop26h 11mMultiple Airlines
Wed 9/311:36 amORD - SWF
2 stops24h 38mMultiple Airlines
Deal found 8/16$299
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/217:12 pmSWF - RFD
1 stop14h 28mAllegiant Air
Thu 9/2511:00 amRFD - SWF
1 stop23h 03mAllegiant Air
Deal found 8/16$305
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/2211:53 amSWF - RFD
1 stop22h 37mAllegiant Air
Sun 9/2811:00 amRFD - SWF
1 stop23h 03mAllegiant Air
Deal found 8/16$328
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/187:12 pmSWF - RFD
1 stop13h 48mAllegiant Air
Sun 9/2811:00 amRFD - SWF
1 stop23h 03mAllegiant Air
Deal found 8/16$342

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 August 18, 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 - MDW

SWFMDW

New Windsor Stewart

Thu 9/25

7:12 pm-12:44 pm

1 stop18h 32m

Chicago Midway

Sun 9/28

6:21 am-6:22 pm

1 stop11h 01m

$211

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/31

11:31 am-1:03 am

1 stop14h 32m

Chicago O'Hare Intl

Sun 11/2

7:29 pm-11:11 am

1 stop14h 42m

$219

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 10/27

3:01 pm-1:03 am

1 stop11h 02m

Chicago O'Hare Intl

Thu 10/30

7:29 pm-10:41 am

1 stop14h 12m

$244

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/10

11:41 am-11:45 pm

1 stop13h 04m

Chicago O'Hare Intl

Sun 10/12

7:29 pm-10:11 am

1 stop13h 42m

$244

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/3

12:11 pm-10:48 pm

1 stop11h 37m

Chicago O'Hare Intl

Sun 10/5

4:45 pm-10:11 am

1 stop16h 26m

$244

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/24

11:31 am-11:45 pm

1 stop13h 14m

Chicago O'Hare Intl

Sun 10/26

7:29 pm-2:11 pm

1 stop17h 42m

$244

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/17

11:31 am-11:45 pm

1 stop13h 14m

Chicago O'Hare Intl

Sun 10/19

4:45 pm-10:11 am

1 stop16h 26m

$244

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Mon 9/22

11:53 am-9:30 am

1 stop22h 37m

Chicago Greater Rockford

Thu 9/25

11:00 am-11:03 am

1 stop23h 03m

$253

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 9/18

7:12 pm-8:00 am

1 stop13h 48m

Chicago Greater Rockford

Thu 9/25

11:00 am-11:03 am

1 stop23h 03m

$267

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 9/18

7:12 pm-8:00 am

1 stop13h 48m

Chicago Greater Rockford

Sun 9/21

11:00 am-11:03 am

1 stop23h 03m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 43 results
1
2
3
...
5

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, August is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $245). Flying from New Windsor to Chicago in March is currently the most expensive (average of $321). 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 $253, Allegiant Air can have you in Chicago from New Windsor in 22h 37m. 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 Midway or New Windsor Stewart - Chicago Greater Rockford, 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, August is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $245). Flying from New Windsor to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Newark to Midway flights
LaGuardia to Midway flights
LaGuardia to St. Louis flights
Newark to St. Louis flights
Syracuse to O'Hare Intl flights
John F Kennedy Intl to St. Louis flights
White Plains to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Rochester to O'Hare Intl flights
Albany to O'Hare Intl flights
Syracuse to Midway flights
Stewart to O'Hare Intl flights
White Plains to Midway flights
Buffalo to Midway flights
Albany to Midway flights
John F Kennedy Intl to Moline flights
Syracuse to St. Louis flights
LaGuardia to Moline flights
Albany to St. Louis flights
Rochester to Midway flights
Islip to O'Hare Intl flights
Newark to Moline flights
Ithaca to O'Hare Intl flights
Binghamton to Midway flights
Binghamton to O'Hare Intl flights
Newark to Rockford flights
LaGuardia to Peoria flights
White Plains to St. Louis flights
Rochester to St. Louis flights
Elmira to Midway flights
Elmira to O'Hare Intl flights
Elmira to St. Louis flights
Ithaca to Midway flights
Newark to Peoria flights
Binghamton to St. Louis flights
Newark to Bloomington flights
Ithaca to St. Louis flights
John F Kennedy Intl to Bloomington flights
Buffalo to St. Louis flights
Newark to Springfield flights
LaGuardia to Bloomington flights
John F Kennedy Intl to Springfield flights
Syracuse to Peoria flights
Newark to Evansville flights
White Plains to Bloomington flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.