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Stewart

$118+ Cheap flights from O'Hare Intl (ORD) to New Windsor (SWF)

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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Stewart (SWF). 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 August 14, 2025.

Round-trip from

$224
(Mytrip)

One-way from

$118
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$218
From Chicago O'Hare Intl to New Windsor Stewart
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One-way flight from Chicago O'Hare Intl to New Windsor Stewart
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Highest demand for flights based on searches. 3% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from O'Hare Intl to Stewart

Cheapest flights from O'Hare Intl to Stewart
Explore the most affordable flight options available from O'Hare Intl to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:44 pmORD - SWF
1 stop15h 37mMultiple Airlines
Mon 10/611:01 amSWF - ORD
1 stop12h 47mMultiple Airlines
Deal found 8/12$224
This Mytrip deal was found by Cheapflights users on 8/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:29 pmORD - SWF
1 stop14h 12mMultiple Airlines
Mon 10/2011:01 amSWF - ORD
1 stop8h 23mMultiple Airlines
Deal found 8/14$244
This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:11 pmORD - SWF
1 stop14h 40mMultiple Airlines
Mon 10/2011:01 amSWF - ORD
1 stop8h 05mMultiple Airlines
Deal found 8/12$254
This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/225:05 amORD - SWF
1 stop10h 41mMultiple Airlines
Mon 8/255:36 pmSWF - ORD
1 stop17h 55mMultiple Airlines
Deal found 8/12$292
This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/255:05 amORD - SWF
1 stop10h 41mMultiple Airlines
Fri 8/291:55 pmSWF - ORD
1 stop11h 04mMultiple Airlines
Deal found 8/12$303
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Tue 11/255:59 pmORD - SWF
1 stop16h 28mMultiple Airlines
Fri 12/512:27 pmSWF - ORD
1 stop21h 56mMultiple Airlines
Deal found 8/12$360
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 11/235:59 pmORD - SWF
1 stop15h 08mMultiple Airlines
Fri 12/512:27 pmSWF - ORD
1 stop21h 56mMultiple Airlines
Deal found 8/12$369
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 8/2410:12 amORD - SWF
1 stop6h 48mMultiple Airlines
Fri 8/291:55 pmSWF - ORD
1 stop11h 04mMultiple Airlines
Deal found 8/13$416
This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1810:26 amORD - SWF
1 stop7h 21mMultiple Airlines
Fri 8/225:36 pmSWF - ORD
1 stop17h 55mMultiple Airlines
Deal found 8/12$430
This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2110:12 amORD - SWF
1 stop6h 48mMultiple Airlines
Sat 8/232:32 pmSWF - ORD
2 stops10h 27mMultiple Airlines
Deal found 8/12$481

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Stewart 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 August 14, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to New Windsor that are best for you.

Fly from

O'Hare Intl

Fly to

Stewart

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/2

6:44 pm-11:21 am

1 stop15h 37m

New Windsor Stewart

Mon 10/6

11:01 am-10:48 pm

1 stop12h 47m

$224

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/16

7:29 pm-10:41 am

1 stop14h 12m

New Windsor Stewart

Mon 10/20

11:01 am-6:24 pm

1 stop8h 23m

$244

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/9

7:11 pm-10:51 am

1 stop14h 40m

New Windsor Stewart

Mon 10/20

11:01 am-6:06 pm

1 stop8h 05m

$254

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/6

5:59 pm-10:41 am

1 stop15h 42m

New Windsor Stewart

Mon 11/10

12:01 pm-11:42 pm

1 stop12h 41m

$254

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 8/22

5:05 am-4:46 pm

1 stop10h 41m

New Windsor Stewart

Mon 8/25

5:36 pm-10:31 am

1 stop17h 55m

$292

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Mon 8/25

5:05 am-4:46 pm

1 stop10h 41m

New Windsor Stewart

Fri 8/29

1:55 pm-11:59 pm

1 stop11h 04m

$303

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 8/24

10:12 am-6:00 pm

1 stop6h 48m

New Windsor Stewart

Fri 8/29

1:55 pm-11:59 pm

1 stop11h 04m

$416

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Mon 8/18

10:26 am-6:47 pm

1 stop7h 21m

New Windsor Stewart

Fri 8/22

5:36 pm-10:31 am

1 stop17h 55m

$430

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 8/21

10:12 am-6:00 pm

1 stop6h 48m

New Windsor Stewart

Sat 8/23

2:32 pm-11:59 pm

2 stops10h 27m

$481

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 8/21

10:12 am-6:00 pm

1 stop6h 48m

New Windsor Stewart

Mon 8/25

12:17 pm-11:59 pm

2 stops12h 42m

$493

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 19 results
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Best time to book a flight from O'Hare Intl to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from O'Hare Intl 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 Chicago O'Hare Intl Airport to New Windsor

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

Currently, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to New Windsor (average of $109). Flying from Chicago O'Hare Intl Airport to New Windsor in December is currently the most expensive (average of $202). 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 O'Hare Intl to Stewart. 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 into for flights to New Windsor from Chicago O'Hare Intl?

    Located just 4.3 mi from the city center, New Windsor Stewart is the airport most travelers will use when flying to New Windsor from Chicago O'Hare Intl. Booking flights from Chicago O'Hare Intl to Stewart (SWF) should be relatively easy as there are 0 daily inbound flights from Chicago O'Hare Intl from 0 different airlines.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to New Windsor (average of $109). Flying from Chicago O'Hare Intl Airport to New Windsor in December is currently the most expensive (average of $202). 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 New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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Alternative routes for O'Hare Intl to Stewart

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Midway to Stewart flights

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