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Stewart

$103+ 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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Aug 6 — Aug 131
Thu 8/6
Thu 8/13
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 July 7, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/5. 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 9/302:03 pm
ORD
-
SWF
2 stops18h 35m
Multiple Airlines
Sun 10/411:48 am
SWF
-
ORD
1 stop28h 38m
Multiple Airlines
Deal found 7/5$301
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 8/18:05 am
ORD
-
SWF
1 stop24h 33m
Multiple Airlines
Thu 8/1310:28 am
SWF
-
ORD
1 stop26h 47m
Multiple Airlines
Deal found 7/6$302
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 8/58:05 am
ORD
-
SWF
1 stop24h 33m
Multiple Airlines
Thu 8/201:00 pm
SWF
-
ORD
1 stop24h 50m
Multiple Airlines
Deal found 7/6$307
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 8/308:05 am
ORD
-
SWF
1 stop9h 36m
Multiple Airlines
Mon 8/3111:10 am
SWF
-
ORD
2 stops12h 58m
Multiple Airlines
Deal found 7/2$324
This Kiwi.com deal was found by Cheapflights users on 7/5. 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 8/198:05 am
ORD
-
SWF
1 stop27h 05m
Multiple Airlines
Wed 8/2612:05 pm
SWF
-
ORD
2 stops12h 03m
Multiple Airlines
Deal found 7/5$337
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 8/265:59 pm
ORD
-
SWF
1 stop14h 54m
Multiple Airlines
Tue 9/111:48 am
SWF
-
ORD
1 stop12h 20m
Multiple Airlines
Deal found 7/6$387
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/1710:16 am
ORD
-
SWF
1 stop23h 52m
Multiple Airlines
Mon 8/2412:17 pm
SWF
-
ORD
2 stops11h 51m
Multiple Airlines
Deal found 7/3$396
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/155:13 pm
ORD
-
SWF
1 stop15h 40m
Multiple Airlines
Tue 8/1811:48 am
SWF
-
ORD
1 stop12h 20m
Multiple Airlines
Deal found 7/3$417
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 7/138:58 pm
ORD
-
SWF
2 stops37h 27m
Multiple Airlines
Thu 8/1310:28 am
SWF
-
ORD
1 stop26h 47m
Multiple Airlines
Deal found 7/6$432
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/85:13 pm
ORD
-
SWF
1 stop15h 40m
Multiple Airlines
Tue 8/1111:48 am
SWF
-
ORD
1 stop12h 22m
Multiple Airlines
Deal found 7/3$466

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 July 7, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$301
(Kiwi.com)

One-way from

$103
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$259
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. 18% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 7, 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 8/1

8:05 am-9:38 am

1 stop24h 33m

New Windsor Stewart

Thu 8/13

10:28 am-12:15 pm

1 stop26h 47m

$302
Quickest round-trip

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 9/3

8:05 am-6:40 pm

1 stop9h 35m

New Windsor Stewart

Mon 9/7

12:16 pm-11:08 pm

1 stop11h 52m

$302

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 8/5

1:50 pm-9:38 am

2 stops18h 48m

New Windsor Stewart

Thu 8/20

1:00 pm-12:50 pm

1 stop24h 50m

$349

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Mon 7/13

8:58 pm-11:25 am

2 stops37h 27m

New Windsor Stewart

Thu 8/13

10:28 am-12:15 pm

1 stop26h 47m

$432

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 8/12

5:13 pm-9:53 am

1 stop15h 40m

New Windsor Stewart

Mon 8/17

12:17 pm-11:10 pm

2 stops11h 53m

$523

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Wed 7/22

5:13 pm-9:53 am

1 stop15h 40m

New Windsor Stewart

Tue 7/28

11:48 am-11:10 pm

1 stop12h 22m

$526

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Fri 9/18

9:26 am-11:39 am

2 stops25h 13m

New Windsor Stewart

Sun 9/20

10:56 am-11:55 pm

1 stop13h 59m

$565

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 7/18

1:50 pm-9:53 am

2 stops19h 03m

New Windsor Stewart

Tue 7/21

11:48 am-11:10 pm

1 stop12h 22m

$567

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 9/5

7:44 pm-9:53 am

1 stop13h 09m

New Windsor Stewart

Mon 9/7

12:17 pm-11:08 pm

2 stops11h 51m

$625
Cheapest one-way
Quickest one-way

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 9/3

8:05 am-6:40 pm

1 stop9h 35m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/5

Showing 1-10 of 20 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-New Windsor flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago O'Hare Intl Airport-New Windsor flight deals on Cheapflights vs. Expedia <90% 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.

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.

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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