$106+ Cheap flights from O'Hare Intl (ORD) to New Windsor (SWF)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Oct 4 — Oct 111
Round-trip
1 adult, Economy
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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
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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
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One-way
Cheapest flights from O'Hare Intl to StewartExplore 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 September 4, 2026.
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 September 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 10/248:04 am -
1 stop26h 04m
Thu 10/2910:38 am -
1 stop29h 59m
Deal found 8/30![Multiple Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Thu 12/35:00 am -
1 stop11h 59m
Sun 12/66:49 pm -
1 stop19h 01m
Deal found 9/2![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 8/31. 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 11/198:00 am -
1 stop8h 58m
Sun 11/226:48 pm -
1 stop30h 28m
Deal found 8/31![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Wed 9/307:11 am -
1 stop25h 27m
Mon 10/57:13 pm -
2 stops24h 10m
Deal found 9/3![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Wed 9/307:11 am -
1 stop25h 27m
Sun 10/411:48 am -
2 stops22h 32m
Deal found 9/3![Multiple Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 10/218:04 am -
1 stop24h 44m
Sun 10/2511:58 am -
2 stops22h 23m
Deal found 9/1![Multiple Airlines logo]()
$286
Best flights from O'Hare Intl to StewartDiscover carefully curated flight deals from O'Hare Intl to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
Discover carefully curated flight deals from O'Hare Intl to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 12/35:00 am -
1 stop11h 59m
Sun 12/66:49 pm -
1 stop19h 01m
Deal found 9/1![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Wed 9/307:11 am -
1 stop25h 27m
Sun 10/411:48 am -
2 stops22h 32m
Deal found 9/3![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Wed 10/218:04 am -
1 stop24h 44m
Sun 10/2511:58 am -
2 stops22h 23m
Deal found 9/2![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 10/248:04 am -
1 stop26h 04m
Mon 10/267:01 pm -
1 stop23h 02m
Deal found 8/30![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 8/31. 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 10/218:04 am -
1 stop24h 44m
Mon 10/267:01 pm -
1 stop23h 02m
Deal found 8/31![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/37:11 am -
1 stop26h 47m
Sat 10/1012:39 pm -
2 stops45h 42m
Deal found 9/3![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 10/148:30 am -
2 stops23h 58m
Sun 10/1811:53 am -
1 stop28h 37m
Deal found 9/1![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Thu 10/17:28 pm -
2 stops39h 11m
Thu 10/810:18 am -
1 stop30h 12m
Deal found 9/2![Multiple Airlines logo]()
$355
Last-minute flights from O'Hare Intl to StewartDiscover last-minute flight deals from O'Hare Intl to Stewart. Data last updated September 4, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Stewart. Data last updated September 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Wed 9/307:11 am -
1 stop25h 27m
Sun 10/411:48 am -
2 stops22h 32m
Deal found 9/3![Multiple Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 9/307:11 am -
1 stop25h 27m
Mon 10/57:13 pm -
2 stops41h 38m
Deal found 9/4![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 9/3. 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.
Wed 10/218:04 am -
1 stop24h 44m
Sun 10/2511:58 am -
2 stops22h 23m
Deal found 9/3![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 8/31. 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 10/218:04 am -
1 stop24h 44m
Mon 10/267:01 pm -
2 stops24h 44m
Deal found 8/31![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 10/248:04 am -
1 stop26h 04m
Thu 10/2910:38 am -
1 stop29h 59m
Deal found 8/30![Multiple Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/31. 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 10/248:04 am -
1 stop26h 04m
Mon 10/267:01 pm -
1 stop23h 02m
Deal found 8/31![Multiple Airlines logo]()
$293
One-way flights from O'Hare Intl to StewartSearch for one-way flight options from O'Hare Intl to Stewart. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
Search for one-way flight options from O'Hare Intl to Stewart. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 10/318:00 am -
1 stop27h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 10/218:04 am -
1 stop24h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 9/307:11 am -
1 stop25h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 10/148:04 am -
1 stop24h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 10/37:11 am -
1 stop26h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Multiple Airlines logo]()
$120
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 September 4, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $232 (Kiwi.com) |
One-way from | $106 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $249 |
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 7,457,451 searches. Data last updated September 4, 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
Cheapest round-trip
Quickest round-trip
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 9/30
7:11 am-9:38 am
1 stop25h 27m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$123
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Sat 10/17
8:04 am-11:03 am
1 stop25h 59m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Tue 10/27
7:50 pm-9:48 am
2 stops36h 58m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$173
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Mon 11/2
7:50 pm-11:39 am
2 stops38h 49m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Thu 11/5
7:50 pm-11:39 am
2 stops38h 49m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Thu 10/1
7:28 pm-11:39 am
2 stops39h 11m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$186
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Fri 10/2
7:28 pm-10:58 am
2 stops38h 30m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$192
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Sat 9/26
6:20 am-10:23 am
2 stops27h 03m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$200
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Mon 9/28
7:28 pm-11:39 am
2 stops39h 11m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$211
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 9/16
7:28 pm-10:16 am
2 stops37h 48m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$212
Showing 1-10 of 19 resultsSorted by cheapest first
- 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.
ORD-SWF
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.
Traveling to a place near New Windsor?
Book flights to New Windsor if you plan to visit one of these locationsKingston
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