HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$78+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CHI
Dec 29 — Jan 51
Mon 12/29
Mon 1/5
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.

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 November 29, 2025.

This Mytrip deal was found by Cheapflights users on 11/29. 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 12/1212:27 pmSWF - ORD
1 stop8h 34mMultiple Airlines
Sun 12/141:52 pmORD - SWF
2 stops20h 45mMultiple Airlines
Deal found 11/29$271
This Kiwi.com deal was found by Cheapflights users on 11/29. 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 12/1411:43 amSWF - ORD
1 stop27h 38mMultiple Airlines
Thu 12/1812:39 pmORD - SWF
2 stops28h 27mMultiple Airlines
Deal found 11/29$291
This Mytrip deal was found by Cheapflights users on 11/28. 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.
Fri 12/512:27 pmSWF - ORD
1 stop8h 34mMultiple Airlines
Sun 12/71:52 pmORD - SWF
2 stops20h 45mMultiple Airlines
Deal found 11/28$303
This Booking.com deal was found by Cheapflights users on 11/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/127:30 pmSWF - RFD
1 stop18h 18mAllegiant Air
Mon 12/1510:38 amRFD - SWF
1 stop7h 02mAllegiant Air
Deal found 11/28$316
This Kiwi.com deal was found by Cheapflights users on 11/29. 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 12/207:50 pmSWF - MDW
1 stop14h 33mAllegiant Air
Tue 12/239:43 amMDW - SWF
1 stop23h 07mAllegiant Air
Deal found 11/29$403
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:25 pmSWF - ORD
1 stop20h 17mMultiple Airlines
Tue 12/3010:22 pmORD - SWF
2 stops35h 41mMultiple Airlines
Deal found 11/26$417
This Mytrip deal was found by Cheapflights users on 11/28. 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.
Fri 12/512:27 pmSWF - ORD
1 stop8h 34mMultiple Airlines
Fri 12/195:00 amORD - SWF
1 stop12h 06mMultiple Airlines
Deal found 11/28$427
This Mytrip deal was found by Cheapflights users on 11/29. 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 12/198:11 pmSWF - RFD
1 stop12h 57mAllegiant Air
Mon 12/2210:18 amRFD - SWF
1 stop7h 02mAllegiant Air
Deal found 11/29$469
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:25 pmSWF - ORD
1 stop20h 17mMultiple Airlines
Sun 12/288:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Deal found 11/28$490
This Mytrip deal was found by Cheapflights users on 11/28. 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.
Fri 12/196:56 pmSWF - ORD
1 stop17h 18mMultiple Airlines
Sun 12/219:09 pmORD - SWF
2 stops21h 26mMultiple Airlines
Deal found 11/28$512
This Kiwi.com deal was found by Cheapflights users on 11/29. 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 12/1912:24 pmSWF - ORD
2 stops37h 06mMultiple Airlines
Sat 1/35:08 pmORD - SWF
1 stop15h 51mMultiple Airlines
Deal found 11/29$549
This Mytrip deal was found by Cheapflights users on 11/28. 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.
Wed 12/2410:40 amSWF - RFD
1 stop8h 16mAllegiant Air
Sun 12/287:24 pmRFD - SWF
1 stop13h 06mAllegiant Air
Deal found 11/28$627

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 November 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$215
(Mytrip)

One-way from

$78
(Mytrip)

Popular in

August

Cheapest in

January

Average price

$236
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. 8% potential increase in price ($21 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 November 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 November 29, 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 1/16

11:09 am-11:46 pm

1 stop13h 37m

Chicago O'Hare Intl

Sun 1/18

5:32 pm-10:19 am

1 stop15h 47m

$246

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/12

12:27 pm-8:01 pm

1 stop8h 34m

Chicago O'Hare Intl

Sun 12/14

1:52 pm-11:37 am

2 stops20h 45m

$271

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 12/14

11:43 am-2:21 pm

1 stop27h 38m

Chicago O'Hare Intl

Thu 12/18

12:39 pm-6:06 pm

2 stops28h 27m

$291

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/5

12:27 pm-8:01 pm

1 stop8h 34m

Chicago O'Hare Intl

Sun 12/7

1:52 pm-11:37 am

2 stops20h 45m

$303

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Fri 12/12

7:30 pm-12:48 pm

1 stop18h 18m

Chicago Greater Rockford

Mon 12/15

10:38 am-6:40 pm

1 stop7h 02m

$316

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 2/12

11:42 am-12:18 am

1 stop13h 36m

Chicago O'Hare Intl

Sun 2/15

9:03 am-10:14 am

2 stops24h 11m

$362

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 2/19

12:22 pm-8:54 pm

1 stop9h 32m

Chicago O'Hare Intl

Sat 2/21

8:42 pm-5:12 pm

2 stops19h 30m

$368

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sat 12/20

7:50 pm-9:23 am

1 stop14h 33m

Chicago Midway

Tue 12/23

9:43 am-9:50 am

1 stop23h 07m

$403

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 12/22

8:25 pm-3:42 pm

1 stop20h 17m

Chicago O'Hare Intl

Tue 12/30

10:22 pm-11:03 am

2 stops35h 41m

$417

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/5

12:27 pm-8:01 pm

1 stop8h 34m

Chicago O'Hare Intl

Fri 12/19

5:00 am-6:06 pm

1 stop12h 06m

$427

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/28

Showing 1-10 of 34 results
1
2
3
4

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 November.
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, May is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $55). 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 $316, Allegiant Air can have you in Chicago from New Windsor in 18h 18m. 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, May is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $55). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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
LaGuardia to Midway flights
LaGuardia to St. Louis flights
John F Kennedy Intl to St. Louis flights
Newark to St. Louis flights
Newark to Midway flights
Buffalo to O'Hare Intl flights
Syracuse to O'Hare Intl flights
Albany to O'Hare Intl flights
White Plains to O'Hare Intl flights
Rochester to O'Hare Intl flights
Syracuse to Midway flights
John F Kennedy Intl to Moline flights
Newark to Moline flights
LaGuardia to Moline flights
Buffalo to Midway flights
Albany to Midway flights
Albany to St. Louis flights
Stewart to O'Hare Intl flights
White Plains to St. Louis flights
White Plains to Midway flights
Rochester to Midway flights
Buffalo to St. Louis flights
Ithaca to St. Louis flights
Islip to O'Hare Intl flights
Ithaca to O'Hare Intl flights
Syracuse to St. Louis flights
LaGuardia to Peoria flights
Rochester to St. Louis flights
Newark to Peoria flights
Newark to Champaign flights
LaGuardia to Evansville flights
Elmira to St. Louis flights
Elmira to O'Hare Intl flights
Syracuse to Moline flights
Stewart to Rockford flights
Newark to Evansville flights
Newark to Bloomington flights
John F Kennedy Intl to Evansville flights
Albany to Moline flights
White Plains to Evansville flights
Binghamton to Midway flights
Albany to Peoria flights
Ithaca to Midway flights
Elmira to Midway flights
John F Kennedy Intl to Champaign flights
Buffalo to Moline 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.