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O'Hare Intl

$90+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORD
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$201
(Kiwi.com)

One-way from

$90
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$185
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. 4% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Mon 10/273:01 pmSWF - ORD
1 stop11h 02mMultiple Airlines
Thu 11/610:49 amORD - SWF
1 stop22h 52mMultiple Airlines
Deal found 9/11$217
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Fri 10/2411:31 amSWF - ORD
2 stops13h 13mMultiple Airlines
Sun 10/262:14 pmORD - SWF
1 stop22h 57mMultiple Airlines
Deal found 9/10$245
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Mon 10/273:01 pmSWF - ORD
2 stops22h 52mMultiple Airlines
Sun 11/27:43 pmORD - SWF
1 stop14h 28mMultiple Airlines
Deal found 9/11$260
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Mon 10/273:01 pmSWF - ORD
1 stop11h 02mMultiple Airlines
Wed 11/510:18 amORD - SWF
1 stop23h 45mMultiple Airlines
Deal found 9/11$270
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Mon 10/273:01 pmSWF - ORD
1 stop11h 02mMultiple Airlines
Sat 11/15:28 pmORD - SWF
1 stop17h 35mMultiple Airlines
Deal found 9/11$276
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/97:11 pmSWF - ORD
1 stop15h 57mMultiple Airlines
Sat 10/116:00 pmORD - SWF
1 stop23h 21mMultiple Airlines
Deal found 9/10$340
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Thu 10/1611:43 amSWF - ORD
1 stop10h 50mMultiple Airlines
Sun 10/196:58 pmORD - SWF
2 stops15h 46mMultiple Airlines
Deal found 9/11$533
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/1811:43 amSWF - ORD
1 stop9h 01mMultiple Airlines
Sun 9/218:49 pmORD - SWF
2 stops13h 55mMultiple Airlines
Deal found 9/10$574

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 September 11, 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

Mon 10/27

3:01 pm-1:03 am

1 stop11h 02m

Chicago O'Hare Intl

Thu 11/6

10:49 am-10:41 am

1 stop22h 52m

$217

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/24

11:31 am-10:50 am

1 stop24h 19m

Chicago O'Hare Intl

Sun 10/26

7:43 pm-2:11 pm

1 stop17h 28m

$217

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 10/27

3:01 pm-1:03 am

1 stop11h 02m

Chicago O'Hare Intl

Sun 11/2

2:14 pm-11:11 am

1 stop19h 57m

$217

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 10/27

3:01 pm-1:03 am

1 stop11h 02m

Chicago O'Hare Intl

Wed 11/5

10:18 am-11:03 am

1 stop23h 45m

$270

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 10/27

3:01 pm-1:03 am

1 stop11h 02m

Chicago O'Hare Intl

Sat 11/1

5:28 pm-12:03 pm

1 stop17h 35m

$276

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 10/9

7:11 pm-10:08 am

1 stop15h 57m

Chicago O'Hare Intl

Sat 10/11

6:00 pm-6:21 pm

1 stop23h 21m

$340

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/3

12:11 pm-10:52 am

1 stop23h 41m

$90

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/5

12:27 pm-9:00 pm

1 stop9h 33m

$109

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/17

11:31 am-11:45 pm

1 stop13h 14m

$109

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/14

11:01 am-9:00 pm

1 stop10h 59m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 14 results
1
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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, August is the cheapest month in which you can book a flight from New Windsor to Chicago O'Hare Intl Airport (average of $245). Flying from New Windsor to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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, August is the cheapest month in which you can book a flight from New Windsor to Chicago O'Hare Intl Airport (average of $245). Flying from New Windsor to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Beloit
Racine
Rockford
Orland Park
Oak Brook
Downers Grove
Naperville
Elk Grove Village
Evanston
Merrillville
Bridgeview
Warrenville

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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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