HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$97+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 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 2/13:05 pm
ORD
-
SWF
1 stop18h 14m
Multiple Airlines
Fri 2/611:09 am
SWF
-
ORD
1 stop13h 38m
Multiple Airlines
Deal found 1/19$269
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.
Wed 2/48:10 am
ORD
-
SWF
2 stops25h 58m
Multiple Airlines
Sun 2/811:48 am
SWF
-
ORD
1 stop8h 53m
Multiple Airlines
Deal found 1/20$329
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.
Wed 6/105:32 pm
ORD
-
SWF
1 stop15h 06m
Multiple Airlines
Mon 6/1512:15 pm
SWF
-
ORD
2 stops29h 55m
Multiple Airlines
Deal found 1/19$348
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.
Wed 6/105:32 pm
ORD
-
SWF
1 stop15h 06m
Multiple Airlines
Wed 6/1712:05 pm
SWF
-
ORD
2 stops20h 54m
Multiple Airlines
Deal found 1/19$363
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.
Sat 2/79:25 am
ORD
-
SWF
1 stop24h 43m
Multiple Airlines
Thu 2/1211:42 am
SWF
-
ORD
1 stop12h 42m
Multiple Airlines
Deal found 1/20$368
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.
Fri 5/17:20 pm
ORD
-
SWF
2 stops38h 35m
Multiple Airlines
Fri 5/811:40 am
SWF
-
ORD
1 stop12h 32m
Multiple Airlines
Deal found 1/20$382
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 6/113:49 pm
ORD
-
SWF
1 stop16h 00m
Multiple Airlines
Wed 6/1712:05 pm
SWF
-
ORD
2 stops20h 54m
Multiple Airlines
Deal found 1/19$479

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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$329
(Kiwi.com)

One-way from

$97
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$153
Provider with most accurate pricing for Chicago O'Hare Intl-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-New Windsor Stewart flights.
Search Deals
From Chicago O'Hare Intl to New Windsor Stewart
Search Deals
One-way flight from Chicago O'Hare Intl to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 21, 2026.
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

Sun 2/1

3:05 pm-10:19 am

1 stop18h 14m

New Windsor Stewart

Fri 2/6

11:09 am-11:47 pm

1 stop13h 38m

$269

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 2/4

8:10 am-11:08 am

2 stops25h 58m

New Windsor Stewart

Sun 2/8

11:48 am-7:41 pm

1 stop8h 53m

$329

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 2/7

9:25 am-11:08 am

1 stop24h 43m

New Windsor Stewart

Thu 2/12

11:42 am-11:24 pm

1 stop12h 42m

$368

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 2/20

9:07 pm-12:39 pm

1 stop14h 32m

New Windsor Stewart

Sun 2/22

11:52 am-7:54 am

2 stops21h 02m

$492

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 2/13

5:24 pm-12:39 pm

2 stops18h 15m

New Windsor Stewart

Sun 2/15

11:42 am-11:47 pm

1 stop13h 05m

$501

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 2/13

9:07 pm-12:39 pm

1 stop14h 32m

New Windsor Stewart

Mon 2/16

12:11 pm-11:22 am

2 stops24h 11m

$523

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 3/4

8:16 pm-9:19 am

1 stop12h 03m

$98

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 5/20

5:32 pm-9:38 am

1 stop15h 06m

$98

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 2/28

12:06 pm-11:02 am

1 stop21h 56m

$121

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 3/25

8:41 pm-9:39 am

1 stop11h 58m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 17 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 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 Chicago O'Hare Intl Airport-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-New Windsor flight deals on Cheapflights vs. FlightHub >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 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 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 $36). Flying from Chicago O'Hare Intl Airport to New Windsor in July is currently the most expensive (average of $103). 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 $36). Flying from Chicago O'Hare Intl Airport to New Windsor in July is currently the most expensive (average of $103). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for O'Hare Intl to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
Midway to Newark flights
Midway to John F Kennedy Intl flights
Midway to LaGuardia flights
O'Hare Intl to Buffalo flights
O'Hare Intl to Syracuse flights
O'Hare Intl to Rochester flights
O'Hare Intl to White Plains flights
O'Hare Intl to Albany flights
Midway to Albany flights
Midway to Buffalo flights
Midway to Syracuse flights
Midway to Rochester flights
O'Hare Intl to Islip flights
Midway to White Plains flights
O'Hare Intl to Ithaca flights
O'Hare Intl to Elmira flights
Midway to Ithaca flights
O'Hare Intl to Binghamton flights
Midway to Binghamton flights
O'Hare Intl to Saranac Lake flights
O'Hare Intl to Watertown flights
Midway to Stewart flights
O'Hare Intl to Plattsburgh flights
O'Hare Intl to Rutland flights
O'Hare Intl to Niagara Falls flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.