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O'Hare Intl

$106+ Cheap flights from New Windsor (SWF) to O'Hare Intl (ORD)

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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORD
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Stewart to O'Hare Intl

Cheapest flights from Stewart to O'Hare Intl
Explore the most affordable flight options available from Stewart to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/19. 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 3/1512:29 pm
SWF
-
ORD
1 stop23h 52m
Multiple Airlines
Wed 3/186:36 pm
ORD
-
SWF
1 stop14h 03m
Multiple Airlines
Deal found 1/19$242
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/612:11 pm
SWF
-
ORD
2 stops29h 29m
Multiple Airlines
Sun 2/88:43 pm
ORD
-
SWF
1 stop12h 36m
Multiple Airlines
Deal found 1/21$281
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/1912:22 pm
SWF
-
ORD
1 stop12h 02m
Multiple Airlines
Thu 2/265:15 am
ORD
-
SWF
2 stops29h 16m
Multiple Airlines
Deal found 1/20$297
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 2/112:13 pm
SWF
-
ORD
1 stop30h 39m
Multiple Airlines
Thu 2/58:43 pm
ORD
-
SWF
1 stop12h 36m
Multiple Airlines
Deal found 1/18$299
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/511:48 am
SWF
-
ORD
1 stop8h 53m
Multiple Airlines
Thu 2/125:05 am
ORD
-
SWF
2 stops28h 09m
Multiple Airlines
Deal found 1/20$360
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 6/2912:15 pm
SWF
-
ORD
2 stops20h 44m
Multiple Airlines
Wed 7/155:32 pm
ORD
-
SWF
1 stop15h 06m
Multiple Airlines
Deal found 1/20$393
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 6/1810:28 am
SWF
-
ORD
1 stop10h 20m
Multiple Airlines
Sat 6/204:10 pm
ORD
-
SWF
1 stop15h 48m
Multiple Airlines
Deal found 1/18$423
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 6/1810:28 am
SWF
-
ORD
1 stop10h 20m
Multiple Airlines
Sun 6/2112:41 pm
ORD
-
SWF
1 stop19h 08m
Multiple Airlines
Deal found 1/19$429

Find flight deals from Stewart to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to O'Hare Intl (ORD). 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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$281
(Kiwi.com)

One-way from

$106
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$182
Provider with most accurate pricing for New Windsor Stewart-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-Chicago O'Hare Intl flights.
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From New Windsor Stewart to Chicago O'Hare Intl
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One-way flight from New Windsor Stewart to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to O'Hare Intl 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 January 21, 2026.
Use the filters below to find and compare flights from New Windsor to Chicago O'Hare Intl Airport that are best for you.

Fly from

Stewart

Fly to

O'Hare Intl

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 3/15

12:29 pm-11:21 am

1 stop23h 52m

Chicago O'Hare Intl

Wed 3/18

6:36 pm-9:39 am

1 stop14h 03m

$242

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 2/6

12:11 pm-4:40 pm

2 stops29h 29m

Chicago O'Hare Intl

Sun 2/8

8:43 pm-10:19 am

1 stop12h 36m

$281

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 2/19

12:22 pm-11:24 pm

1 stop12h 02m

Chicago O'Hare Intl

Thu 2/26

5:15 am-11:31 am

2 stops29h 16m

$297

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 2/1

12:13 pm-5:52 pm

1 stop30h 39m

Chicago O'Hare Intl

Thu 2/5

8:43 pm-10:19 am

1 stop12h 36m

$299

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 2/5

11:48 am-7:41 pm

1 stop8h 53m

Chicago O'Hare Intl

Thu 2/12

5:05 am-10:14 am

2 stops28h 09m

$360

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 6/29

12:15 pm-7:59 am

2 stops20h 44m

Chicago O'Hare Intl

Wed 7/15

5:32 pm-9:38 am

1 stop15h 06m

$393

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 6/18

10:28 am-7:48 pm

1 stop10h 20m

Chicago O'Hare Intl

Sat 6/20

4:10 pm-8:58 am

1 stop15h 48m

$423

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 6/18

10:28 am-7:48 pm

1 stop10h 20m

Chicago O'Hare Intl

Sun 6/21

12:41 pm-8:49 am

1 stop19h 08m

$429

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 2/9

11:09 am-11:47 am

2 stops25h 38m

$106

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 4/16

11:45 am-11:27 am

1 stop24h 42m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 18 results
1
2

Compare providers for flights from Stewart to O'Hare Intl

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 O'Hare Intl in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 O'Hare Intl Airport 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 O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Chicago O'Hare Intl Airport 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 New Windsor-Chicago O'Hare Intl Airport 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 O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 O'Hare Intl Airport

What is the cheapest month to book a flight from New Windsor to Chicago O'Hare Intl Airport?

Currently, November is the cheapest month in which you can book a flight from New Windsor to Chicago O'Hare Intl Airport (average of $55). Flying from New Windsor to Chicago O'Hare Intl Airport 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 O'Hare Intl. 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 O'Hare Intl?

    New Windsor Stewart (SWF) is the airport you will fly out of if you book a flight from New Windsor to Chicago O'Hare Intl. You should not have trouble finding flights to Chicago O'Hare Intl from Stewart; the airport handles an average of 0 outbound flights to Chicago O'Hare Intl per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the New Windsor airport to Chicago O'Hare Intl. It is only a 4.3 mi journey to Stewart (SWF) from New Windsor’s city center.

  • Can I find deals for flights from Stewart to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Stewart to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to O'Hare Intl.

  • Can I find deals for business class flights from Stewart to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Stewart to O'Hare Intl 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 O'Hare Intl Airport?

    Currently, November is the cheapest month in which you can book a flight from New Windsor to Chicago O'Hare Intl Airport (average of $55). Flying from New Windsor to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Bridgeview
Kenosha
Warrenville
Waukegan
Aurora

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