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O'Hare Intl

$107+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORD
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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Find 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 October 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/2111:12 amSWF - ORD
1 stop23h 05mMultiple Airlines
Sun 11/2311:48 amORD - SWF
1 stop21h 19mMultiple Airlines
Deal found 10/27$245
This Mytrip deal was found by Cheapflights users on 10/25. 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 11/711:31 amSWF - ORD
1 stop13h 56mMultiple Airlines
Thu 11/133:26 pmORD - SWF
1 stop17h 45mMultiple Airlines
Deal found 10/25$272
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/2612:17 pmSWF - ORD
1 stop29h 08mMultiple Airlines
Wed 12/34:01 pmORD - SWF
2 stops42h 36mMultiple Airlines
Deal found 10/27$276
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/1411:01 amSWF - ORD
1 stop14h 26mMultiple Airlines
Sun 11/163:26 pmORD - SWF
1 stop18h 45mMultiple Airlines
Deal found 10/27$282
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 10/3111:31 amSWF - ORD
1 stop14h 32mMultiple Airlines
Sun 11/25:11 amORD - SWF
2 stops29h 00mMultiple Airlines
Deal found 10/24$288
This Mytrip deal was found by Cheapflights users on 10/27. 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 11/312:01 pmSWF - ORD
1 stop13h 26mMultiple Airlines
Thu 11/68:28 amORD - SWF
2 stops25h 13mMultiple Airlines
Deal found 10/27$295
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/2410:57 amSWF - ORD
1 stop23h 20mMultiple Airlines
Thu 11/278:45 amORD - SWF
2 stops25h 59mMultiple Airlines
Deal found 10/26$334

Cheap 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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(Mytrip)

One-way from

$107
(Mytrip)

Popular in

August

Cheapest in

January

Average price

$242
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
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Highest demand for flights based on searches. 7% potential increase in price ($19 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 October 2025
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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 October 27, 2025.
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

Fri 1/23

11:09 am-11:42 pm

1 stop13h 33m

Chicago O'Hare Intl

Sun 1/25

5:59 pm-10:19 am

1 stop15h 20m

$229

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/7

11:31 am-12:27 am

1 stop13h 56m

Chicago O'Hare Intl

Thu 11/13

3:26 pm-10:11 am

1 stop17h 45m

$272

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Wed 11/26

12:17 pm-4:25 pm

1 stop29h 08m

Chicago O'Hare Intl

Wed 12/3

4:01 pm-11:37 am

2 stops42h 36m

$276

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 11/24

10:57 am-9:17 am

1 stop23h 20m

Chicago O'Hare Intl

Thu 11/27

8:45 am-11:44 am

2 stops25h 59m

$334

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 11/9

11:43 am-11:28 pm

2 stops12h 45m

Chicago O'Hare Intl

Thu 11/13

3:26 pm-10:11 am

1 stop17h 45m

$367

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 11/10

12:01 pm-9:47 am

1 stop22h 46m

Chicago O'Hare Intl

Fri 11/14

10:43 pm-11:03 am

2 stops35h 20m

$367

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/19

6:56 pm-11:14 am

1 stop17h 18m

Chicago O'Hare Intl

Sun 12/21

7:57 pm-7:35 pm

2 stops22h 38m

$373

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 12/22

8:25 pm-11:14 am

1 stop15h 49m

Chicago O'Hare Intl

Sun 12/28

12:09 pm-10:47 am

2 stops21h 38m

$416

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/5

12:27 pm-8:01 pm

1 stop8h 34m

$112

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 11/24

10:57 am-11:13 pm

1 stop13h 16m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 16 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 October.
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 O'Hare Intl Airport 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 O'Hare Intl Airport flight deals on Cheapflights vs. eDreams >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 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 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 $66). 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 $66). 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
Skokie
Des Plaines
Gurnee
Hoffman Estates
Elgin
Oak Brook
Elk Grove Village
Beloit
Rockford
Naperville
Racine
Downers Grove
Orland Park
Merrillville
Bridgeview
Warrenville
Joliet
Waukegan

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Alternative routes for Stewart to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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