$113+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Dec 5 — Dec 121
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
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
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Last-minute
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 November 5, 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 November 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/310:29 pm -
2 stops36h 10m
Thu 12/106:49 pm -
1 stop20h 10m
Deal found 11/1![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/23:55 pm -
2 stops17h 31m
Thu 12/106:49 pm -
1 stop20h 10m
Deal found 11/1![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/127:55 am -
2 stops50h 44m
Thu 11/196:48 pm -
1 stop29h 46m
Deal found 11/1![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Thu 12/36:10 am -
1 stop10h 49m
Sat 12/512:29 pm -
2 stops13h 25m
Deal found 11/4![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Tue 12/13:55 pm -
2 stops18h 44m
Thu 12/106:49 pm -
1 stop20h 10m
Deal found 11/1![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Thu 12/36:10 am -
1 stop10h 49m
Sun 12/66:49 pm -
2 stops27h 40m
Deal found 11/4![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/36:10 am -
1 stop10h 49m
Sat 12/1212:39 pm -
2 stops13h 29m
Deal found 11/1![Multiple Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/188:59 am -
2 stops24h 17m
Sun 11/226:48 pm -
1 stop29h 46m
Deal found 11/3![Multiple Airlines logo]()
$360
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 November 5, 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 November 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Fri 1/87:52 pm -
2 stops14h 47m
Sun 1/108:01 pm -
1 stop20h 02m
Deal found 11/2![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 1/305:16 pm -
1 stop16h 00m
Sat 2/612:39 pm -
2 stops12h 47m
Deal found 11/3![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/23:55 pm -
2 stops17h 31m
Sun 12/611:06 am -
1 stop15h 02m
Deal found 11/4![Multiple Airlines logo]()
$507
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Fri 1/16:08 am -
1 stop10h 43m
Wed 1/612:39 pm -
2 stops22h 04m
Deal found 11/3![Multiple Airlines logo]()
$516
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Fri 11/209:20 pm -
2 stops13h 19m
Tue 11/2410:59 am -
1 stop13h 35m
Deal found 11/2![Multiple Airlines logo]()
$526
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Mon 12/285:01 am -
1 stop12h 10m
Mon 1/47:01 pm -
1 stop22h 24m
Deal found 11/4![Multiple Airlines logo]()
$541
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/165:24 pm -
1 stop16h 02m
Wed 12/2312:39 pm -
2 stops11h 08m
Deal found 11/1![Multiple Airlines logo]()
$636
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/194:45 pm -
2 stops16h 41m
Sun 1/311:06 am -
1 stop14h 50m
Deal found 11/1![Multiple Airlines logo]()
$662
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 1/285:16 pm -
2 stops16h 41m
Sun 1/3110:56 am -
1 stop14h 59m
Deal found 11/1![Multiple Airlines logo]()
$718
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 2/45:16 pm -
2 stops16h 41m
Sun 2/710:56 am -
1 stop14h 59m
Deal found 11/1![Multiple Airlines logo]()
$728
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Tue 12/225:01 am -
1 stop13h 44m
Tue 12/298:25 pm -
2 stops16h 35m
Deal found 11/1![Multiple Airlines logo]()
$753
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Fri 12/45:24 pm -
2 stops17h 15m
Sun 12/611:06 am -
1 stop15h 02m
Deal found 10/31![Multiple Airlines logo]()
$810
Last-minute flights from O'Hare Intl to StewartDiscover last-minute flight deals from O'Hare Intl to Stewart. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Stewart. Data last updated November 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/127:55 am -
2 stops50h 44m
Thu 11/196:48 pm -
1 stop29h 46m
Deal found 11/1![Multiple Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/188:59 am -
2 stops24h 17m
Sun 11/226:48 pm -
1 stop29h 46m
Deal found 11/3![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Tue 12/13:55 pm -
2 stops18h 44m
Thu 12/106:49 pm -
1 stop20h 10m
Deal found 11/1![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/23:55 pm -
2 stops17h 31m
Thu 12/106:49 pm -
1 stop20h 10m
Deal found 11/1![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/310:29 pm -
2 stops36h 10m
Thu 12/106:49 pm -
1 stop20h 10m
Deal found 11/1![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Thu 12/36:10 am -
1 stop10h 49m
Sat 12/512:29 pm -
2 stops13h 25m
Deal found 11/4![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/36:10 am -
1 stop10h 49m
Wed 12/912:39 pm -
2 stops26h 20m
Deal found 11/1![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Thu 12/36:10 am -
1 stop10h 49m
Sun 12/66:49 pm -
2 stops27h 40m
Deal found 11/4![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/36:10 am -
1 stop10h 49m
Sat 12/1212:39 pm -
2 stops13h 29m
Deal found 11/1![Multiple Airlines logo]()
$335
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 November 5, 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 November 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Tue 1/128:25 am -
2 stops26h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Tue 1/198:25 am -
2 stops26h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 1/138:25 am -
1 stop26h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Multiple Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 2/248:25 am -
1 stop23h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Mon 1/184:47 pm -
2 stops42h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 1/77:10 am -
1 stop11h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Fri 1/228:25 am -
2 stops26h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$141
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 November 5, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $256 (Kiwi.com) |
One-way from | $113 (Kiwi.com) |
Popular in | October |
Cheapest in | January |
Average price | $275 |
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 November 5, 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
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 3/3
8:25 am-9:24 am
1 stop23h 59m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$142
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Fri 1/15
10:18 am-11:39 am
2 stops24h 21m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Fri 1/1
5:58 am-11:39 am
2 stops28h 41m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$171
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 1/20
10:18 am-10:03 am
1 stop22h 45m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$203
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Tue 12/22
5:59 pm-6:56 pm
2 stops23h 57m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$241
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 12/23
5:58 am-11:17 am
2 stops28h 19m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$241
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Tue 12/1
8:15 am-11:49 am
3 stops26h 34m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$243
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Thu 1/14
5:16 pm-10:57 am
2 stops16h 41m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$254
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Tue 11/17
8:59 am-11:39 am
3 stops25h 40m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$260
Quickest round-trip
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 12/9
5:24 pm-10:26 am
1 stop16h 02m
New Windsor Stewart
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$261
Showing 1-10 of 23 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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