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$123+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CHI
Jun 8 — Jun 151
Mon 6/8
Mon 6/15
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 May 9, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/7. 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 8/277:31 pm
SWF
-
ORD
1 stop17h 54m
Multiple Airlines
Tue 9/11:50 pm
ORD
-
SWF
2 stops20h 35m
Multiple Airlines
Deal found 5/7$261
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 5/2312:05 pm
SWF
-
ORD
2 stops36h 08m
Multiple Airlines
Wed 5/275:11 pm
ORD
-
SWF
1 stop14h 47m
Multiple Airlines
Deal found 5/4$262
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 7/2610:28 am
SWF
-
ORD
2 stops22h 25m
Multiple Airlines
Wed 7/298:05 am
ORD
-
SWF
1 stop24h 33m
Multiple Airlines
Deal found 5/8$271
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 8/277:31 pm
SWF
-
ORD
1 stop17h 54m
Multiple Airlines
Mon 8/315:30 pm
ORD
-
SWF
1 stop16h 38m
Multiple Airlines
Deal found 5/7$301
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 7/1210:28 am
SWF
-
ORD
1 stop26h 57m
Multiple Airlines
Wed 7/158:05 am
ORD
-
SWF
1 stop24h 33m
Multiple Airlines
Deal found 5/8$335
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Wed 9/212:05 pm
SWF
-
ORD
2 stops12h 09m
Multiple Airlines
Sun 9/67:55 am
ORD
-
SWF
1 stop9h 45m
Multiple Airlines
Deal found 5/5$346
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 8/277:31 pm
SWF
-
ORD
1 stop17h 54m
Multiple Airlines
Sun 8/305:30 pm
ORD
-
SWF
1 stop16h 36m
Multiple Airlines
Deal found 5/6$367
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/612:05 pm
SWF
-
ORD
2 stops44h 50m
Multiple Airlines
Wed 6/104:59 pm
ORD
-
SWF
1 stop14h 59m
Multiple Airlines
Deal found 5/6$369
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 7/3010:28 am
SWF
-
ORD
1 stop26h 57m
Multiple Airlines
Sat 8/15:13 pm
ORD
-
SWF
1 stop14h 45m
Multiple Airlines
Deal found 5/6$377
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 8/277:31 pm
SWF
-
ORD
1 stop17h 54m
Multiple Airlines
Sat 8/295:30 pm
ORD
-
SWF
1 stop14h 28m
Multiple Airlines
Deal found 5/8$386
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 6/89:39 am
SWF
-
RFD
1 stop10h 24m
Allegiant Air
Wed 6/104:42 pm
RFD
-
SWF
1 stop25h 32m
Allegiant Air
Deal found 5/8$399
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 8/611:45 am
SWF
-
RFD
1 stop21h 04m
Multiple Airlines
Mon 8/106:26 pm
RFD
-
SWF
1 stop15h 42m
Multiple Airlines
Deal found 5/6$401

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 May 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$261
(Kiwi.com)

One-way from

$123
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$266
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. 9% potential increase in price ($24 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 May 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 May 9, 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

Sun 7/12

10:28 am-12:25 pm

1 stop26h 57m

Chicago O'Hare Intl

Wed 7/15

1:50 pm-9:38 am

2 stops18h 48m

$337

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 7/30

10:28 am-12:25 pm

1 stop26h 57m

Chicago O'Hare Intl

Sat 8/1

5:13 pm-8:58 am

1 stop14h 45m

$377

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Mon 6/8

9:39 am-7:03 pm

1 stop10h 24m

Chicago Greater Rockford

Wed 6/10

4:42 pm-7:14 pm

1 stop25h 32m

$399

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Thu 8/6

11:45 am-7:49 am

1 stop21h 04m

Chicago Greater Rockford

Mon 8/10

6:26 pm-11:08 am

1 stop15h 42m

$401

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 5/29

9:41 am-11:13 pm

1 stop14h 32m

Chicago O'Hare Intl

Sun 5/31

6:55 am-8:51 am

2 stops24h 56m

$414

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 7/30

10:28 am-12:25 pm

1 stop26h 57m

Chicago O'Hare Intl

Mon 8/3

5:13 pm-11:08 am

1 stop16h 55m

$416

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sun 5/31

8:10 pm-7:45 am

1 stop12h 35m

Chicago Greater Rockford

Fri 6/5

7:53 pm-11:25 am

2 stops14h 32m

$423

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 8/6

10:28 am-12:25 pm

1 stop26h 57m

Chicago O'Hare Intl

Sun 8/9

5:13 pm-11:37 am

2 stops17h 24m

$424

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sun 7/26

11:45 am-7:49 am

1 stop21h 04m

Chicago Greater Rockford

Wed 7/29

10:03 am-6:56 pm

1 stop7h 53m

$427

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sun 6/21

8:04 pm-7:45 am

1 stop12h 41m

Chicago Greater Rockford

Mon 6/29

7:48 pm-11:08 am

1 stop14h 20m

$441

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/8

Showing 1-10 of 51 resultsSorted by cheapest first
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6

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 May.
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
No data available for this route at this time. Please check back soon.

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 $399, Allegiant Air can have you in Chicago from New Windsor in 10h 24m. 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.

See more FAQs

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