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Stewart

$89+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap 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 December 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Sun 12/284:44 pmORD - SWF
1 stop17h 03mMultiple Airlines
Sat 1/38:45 pmSWF - ORD
2 stops15h 53mMultiple Airlines
Deal found 12/20$857
This Mytrip deal was found by Cheapflights users on 12/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/251:34 pmORD - SWF
2 stops20h 33mMultiple Airlines
Mon 12/2911:37 amSWF - ORD
1 stop13h 53mMultiple Airlines
Deal found 12/20$890
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Sun 12/288:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Thu 1/111:43 amSWF - ORD
1 stop8h 19mMultiple Airlines
Deal found 12/20$939
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Sun 12/288:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Tue 12/3011:43 amSWF - ORD
1 stop8h 19mMultiple Airlines
Deal found 12/20$1,047
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Sun 12/288:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Sun 1/411:43 amSWF - ORD
1 stop8h 16mMultiple Airlines
Deal found 12/21$1,166
This Kiwi.com deal was found by Cheapflights users on 12/19. 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.
Sat 12/205:08 pmORD - SWF
1 stop16h 11mMultiple Airlines
Sat 12/278:45 pmSWF - ORD
1 stop13h 17mMultiple Airlines
Deal found 12/19$1,170
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/218:26 pmORD - SWF
2 stops14h 18mMultiple Airlines
Thu 12/2511:43 amSWF - ORD
1 stop8h 19mMultiple Airlines
Deal found 12/19$1,184

Find 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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$189
(Kiwi.com)

One-way from

$89
(Mytrip)

Popular in

June

Cheapest in

January

Average price

$236
Provider with most accurate pricing for Chicago O'Hare Intl-New Windsor Stewart flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-New Windsor Stewart flights.
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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
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 23, 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 1/22

2:52 pm-10:19 am

1 stop18h 27m

New Windsor Stewart

Mon 1/26

11:09 am-11:22 am

1 stop25h 13m

$189

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Mon 1/19

11:09 am-11:47 am

2 stops25h 38m

$197

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 2/5

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Thu 2/12

11:42 am-9:13 pm

1 stop10h 31m

$277

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:51 pm-11:31 am

2 stops13h 40m

New Windsor Stewart

Fri 1/16

7:33 pm-2:39 pm

1 stop20h 06m

$404

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/1

7:20 am-11:07 am

1 stop26h 47m

New Windsor Stewart

Mon 1/5

11:37 am-12:54 pm

2 stops26h 17m

$478

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 1/4

4:44 pm-10:47 am

1 stop17h 03m

New Windsor Stewart

Thu 1/8

12:13 pm-5:07 pm

2 stops29h 54m

$535

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 1/11

8:27 pm-11:31 am

2 stops14h 04m

New Windsor Stewart

Sun 1/18

12:13 pm-7:51 pm

1 stop8h 38m

$542

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:51 pm-11:31 am

2 stops13h 40m

New Windsor Stewart

Sun 1/18

12:13 pm-7:51 pm

1 stop8h 38m

$575

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:43 pm-10:19 am

1 stop12h 36m

$90

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 2/8

3:00 pm-10:19 am

1 stop18h 19m

$94

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 16 results
1
2

Compare providers for flights from O'Hare Intl to Stewart

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 O'Hare Intl to Stewart in December.
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 Chicago O'Hare Intl Airport-New Windsor flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-New Windsor flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-New Windsor 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 Chicago O'Hare Intl Airport-New Windsor 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 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to New Windsor (average of $37). Flying from Chicago O'Hare Intl Airport to New Windsor in July is currently the most expensive (average of $104). 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to New Windsor (average of $37). Flying from Chicago O'Hare Intl Airport to New Windsor in July is currently the most expensive (average of $104). 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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