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$85+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CHI
May 15 — May 221
Fri 5/15
Fri 5/22
1 adult, Economy
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Cheap 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 April 15, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
Mon 4/2711:40 am
SWF
-
ORD
2 stops30h 20m
Multiple Airlines
Wed 4/297:15 pm
ORD
-
SWF
1 stop14h 40m
Multiple Airlines
Deal found 4/10$237
This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
Thu 4/2311:45 am
SWF
-
ORD
1 stop10h 32m
Multiple Airlines
Sat 4/257:15 pm
ORD
-
SWF
1 stop14h 40m
Multiple Airlines
Deal found 4/10$258
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 4/2611:45 am
SWF
-
ORD
1 stop22h 51m
Multiple Airlines
Thu 4/3011:28 am
ORD
-
SWF
2 stops22h 22m
Multiple Airlines
Deal found 4/13$282
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Sat 7/412:05 pm
SWF
-
ORD
2 stops12h 14m
Multiple Airlines
Wed 7/157:55 am
ORD
-
SWF
1 stop24h 43m
Multiple Airlines
Deal found 4/15$324
This Kiwi.com deal was found by Cheapflights users on 4/12. 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.
Sun 6/218:04 pm
SWF
-
RFD
1 stop12h 41m
Allegiant Air
Sat 7/410:05 am
RFD
-
SWF
1 stop6h 49m
Allegiant Air
Deal found 4/12$344
This Kiwi.com deal was found by Cheapflights users on 4/12. 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.
Thu 5/218:10 pm
SWF
-
ORD
1 stop17h 13m
Multiple Airlines
Tue 5/261:50 pm
ORD
-
SWF
2 stops20h 35m
Multiple Airlines
Deal found 4/12$358
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Thu 5/149:38 am
SWF
-
ORD
1 stop13h 36m
Multiple Airlines
Mon 5/189:37 pm
ORD
-
SWF
2 stops36h 48m
Multiple Airlines
Deal found 4/13$361
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 4/3011:48 am
SWF
-
MDW
1 stop23h 40m
Multiple Airlines
Mon 5/42:15 pm
MDW
-
SWF
2 stops44h 10m
Multiple Airlines
Deal found 4/15$362
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Thu 5/288:10 pm
SWF
-
RFD
1 stop12h 35m
Multiple Airlines
Fri 5/298:03 pm
RFD
-
SWF
2 stops14h 22m
Multiple Airlines
Deal found 4/14$364
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Thu 6/258:04 pm
SWF
-
RFD
1 stop12h 41m
Allegiant Air
Sat 6/2710:07 am
RFD
-
SWF
1 stop8h 03m
Allegiant Air
Deal found 4/13$496
This Kiwi.com deal was found by Cheapflights users on 4/12. 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.
Sun 6/288:04 pm
SWF
-
RFD
1 stop12h 41m
Allegiant Air
Fri 7/107:50 pm
RFD
-
SWF
1 stop21h 04m
Allegiant Air
Deal found 4/12$505
This Kiwi.com deal was found by Cheapflights users on 4/11. 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 6/288:04 pm
SWF
-
RFD
1 stop12h 41m
Allegiant Air
Fri 7/37:50 pm
RFD
-
SWF
1 stop21h 04m
Allegiant Air
Deal found 4/11$518

Find 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 April 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Kiwi.com)

One-way from

$85
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$267
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. 11% potential increase in price ($31 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 April 2026
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 April 15, 2026.
Use the filters below to find and compare flights from New Windsor to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 4/27

11:40 am-5:00 pm

2 stops30h 20m

Chicago O'Hare Intl

Wed 4/29

7:15 pm-10:55 am

1 stop14h 40m

$237

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 4/26

11:45 am-9:36 am

1 stop22h 51m

Chicago O'Hare Intl

Thu 4/30

11:28 am-10:50 am

2 stops22h 22m

$282

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sat 7/4

12:05 pm-11:19 pm

2 stops12h 14m

Chicago O'Hare Intl

Wed 7/15

7:55 am-9:38 am

1 stop24h 43m

$324

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 5/21

8:10 pm-12:23 pm

1 stop17h 13m

Chicago O'Hare Intl

Tue 5/26

1:50 pm-11:25 am

2 stops20h 35m

$358

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 5/14

9:38 am-10:14 pm

1 stop13h 36m

Chicago O'Hare Intl

Mon 5/18

9:37 pm-11:25 am

2 stops36h 48m

$361

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 4/30

11:48 am-10:28 am

1 stop23h 40m

Chicago Midway

Mon 5/4

2:15 pm-11:25 am

2 stops44h 10m

$362

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 5/28

8:10 pm-7:45 am

1 stop12h 35m

Chicago Greater Rockford

Fri 5/29

8:03 pm-11:25 am

2 stops14h 22m

$364

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 8/28

10:56 am-10:27 pm

1 stop12h 31m

Chicago O'Hare Intl

Sat 8/29

8:27 pm-10:27 am

1 stop13h 00m

$367

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 10/8

10:08 am-11:58 pm

1 stop14h 50m

Chicago O'Hare Intl

Mon 10/12

6:15 am-6:11 pm

1 stop10h 56m

$381

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 6/14

8:04 pm-12:23 pm

1 stop17h 19m

Chicago O'Hare Intl

Wed 6/17

1:50 pm-9:38 am

2 stops18h 48m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Showing 1-10 of 45 resultsSorted by cheapest first
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, December is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $48). Flying from New Windsor to Chicago in July is currently the most expensive (average of $119). 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 $496, Allegiant Air can have you in Chicago from New Windsor in 12h 41m. 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, December is the cheapest month in which you can book a flight from New Windsor to Chicago (average of $48). Flying from New Windsor to Chicago in July is currently the most expensive (average of $119). 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?

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