$81+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SWF
Sep 24 — Oct 11
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 August 25, 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 August 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Wed 10/218:04 am -
1 stop24h 44m
Thu 10/2910:38 am -
1 stop29h 59m
Deal found 8/21![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Sat 10/178:04 am -
1 stop25h 59m
Thu 10/2910:38 am -
1 stop29h 59m
Deal found 8/21![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Sat 10/248:04 am -
1 stop26h 04m
Thu 10/2910:38 am -
1 stop29h 59m
Deal found 8/21![Multiple Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 8/24![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Wed 10/218:04 am -
1 stop24h 44m
Sun 10/2511:58 am -
1 stop28h 38m
Deal found 8/21![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 8/24![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 8/24. 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
Fri 10/305:39 pm -
1 stop16h 07m
Deal found 8/24![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Thu 12/35:00 am -
1 stop11h 59m
Sun 12/66:49 pm -
1 stop19h 01m
Deal found 8/21![Multiple Airlines logo]()
$281
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 August 25, 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 August 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Wed 10/218:04 am -
1 stop24h 44m
Thu 10/2910:38 am -
1 stop29h 59m
Deal found 8/21![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Sat 10/178:04 am -
1 stop25h 59m
Thu 10/2910:38 am -
1 stop29h 59m
Deal found 8/21![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 8/24![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 10/77:11 am -
1 stop25h 17m
Sun 10/1110:56 am -
1 stop21h 35m
Deal found 8/24![Multiple Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Fri 12/48:19 pm -
2 stops14h 20m
Sun 12/66:49 pm -
1 stop19h 01m
Deal found 8/21![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 10/238:11 pm -
2 stops14h 28m
Mon 10/267:01 pm -
1 stop23h 02m
Deal found 8/23![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Thu 11/198:00 am -
1 stop8h 58m
Mon 11/2311:29 am -
1 stop22h 49m
Deal found 8/20![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/163:50 pm -
1 stop17h 26m
Wed 9/2312:39 pm -
2 stops22h 41m
Deal found 8/20![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 12/22:31 pm -
1 stop18h 55m
Sun 12/66:49 pm -
1 stop19h 01m
Deal found 8/24![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 10/238:11 pm -
2 stops14h 28m
Fri 10/305:39 pm -
1 stop16h 07m
Deal found 8/23![Multiple Airlines logo]()
$395
Last-minute flights from O'Hare Intl to StewartDiscover last-minute flight deals from O'Hare Intl to Stewart. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Stewart. Data last updated August 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Wed 9/27:44 pm -
1 stop13h 09m
Thu 9/37:30 pm -
2 stops49h 38m
Deal found 8/21![Multiple Airlines logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 9/27:44 pm -
1 stop13h 09m
Fri 9/410:36 am -
2 stops34h 32m
Deal found 8/24![Multiple Airlines logo]()
$477
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 9/57:44 pm -
1 stop13h 09m
Thu 9/1010:56 am -
1 stop13h 03m
Deal found 8/22![Multiple Airlines logo]()
$489
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 9/68:05 am -
1 stop9h 35m
Thu 9/1010:56 am -
2 stops23h 24m
Deal found 8/21![Multiple Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Tue 9/153:50 pm -
2 stops18h 49m
Thu 9/1710:56 am -
1 stop13h 03m
Deal found 8/20![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/163:50 pm -
1 stop17h 26m
Wed 9/2312:39 pm -
2 stops22h 41m
Deal found 8/20![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/163:50 pm -
1 stop17h 26m
Sat 9/1912:39 pm -
2 stops22h 41m
Deal found 8/20![Multiple Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/163:50 pm -
1 stop17h 26m
Mon 9/2112:16 pm -
2 stops11h 43m
Deal found 8/20![Multiple Airlines logo]()
$462
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/163:50 pm -
1 stop17h 26m
Sun 9/2010:56 am -
1 stop24h 24m
Deal found 8/20![Multiple Airlines logo]()
$484
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Thu 9/173:50 pm -
1 stop17h 26m
Sun 9/2010:56 am -
2 stops32h 27m
Deal found 8/21![Multiple Airlines logo]()
$487
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/193:50 pm -
1 stop17h 26m
Wed 9/2312:39 pm -
2 stops22h 41m
Deal found 8/20![Multiple Airlines logo]()
$426
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 August 25, 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 August 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/23. 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
Deal found 8/23![Multiple Airlines logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Wed 9/307:11 am -
1 stop25h 27m
Deal found 8/21![Multiple Airlines logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Wed 10/218:04 am -
1 stop24h 44m
Deal found 8/21![Multiple Airlines logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 10/178:04 am -
1 stop25h 59m
Deal found 8/22![Multiple Airlines logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 8/24. 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
Deal found 8/24![Multiple Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 8/21. 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.
Sat 10/37:11 am -
1 stop26h 47m
Deal found 8/21![Multiple Airlines logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 8/23. 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
Deal found 8/23![Multiple Airlines logo]()
$100
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 August 25, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $189 (Kiwi.com) |
One-way from | $81 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $271 |
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 August 25, 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 10/21
8:04 am-9:48 am
1 stop24h 44m
New Windsor Stewart
Thu 10/29
10:38 am-3:37 pm
1 stop29h 59m
$190
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
Thu 10/29
10:38 am-3:37 pm
1 stop29h 59m
$195
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Thu 12/3
5:00 am-5:59 pm
1 stop11h 59m
New Windsor Stewart
Sun 12/6
6:49 pm-12:50 pm
1 stop19h 01m
$282
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 10/7
7:11 am-9:28 am
1 stop25h 17m
New Windsor Stewart
Sun 10/11
10:56 am-7:31 am
1 stop21h 35m
$313
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Fri 12/4
8:19 pm-11:39 am
2 stops14h 20m
New Windsor Stewart
Sun 12/6
6:49 pm-12:50 pm
1 stop19h 01m
$329
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Fri 10/23
8:11 pm-11:39 am
2 stops14h 28m
New Windsor Stewart
Mon 10/26
7:01 pm-5:03 pm
1 stop23h 02m
$331
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Thu 11/19
8:00 am-5:58 pm
1 stop8h 58m
New Windsor Stewart
Mon 11/23
11:29 am-9:18 am
1 stop22h 49m
$343
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 9/16
3:50 pm-10:16 am
1 stop17h 26m
New Windsor Stewart
Wed 9/23
12:39 pm-10:20 am
2 stops22h 41m
$355
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Wed 12/2
2:31 pm-10:26 am
1 stop18h 55m
New Windsor Stewart
Sun 12/6
6:49 pm-12:50 pm
1 stop19h 01m
$360
Quickest round-trip
ChicagoNew Windsor
ORD Chicago O'Hare Intl - SWF New Windsor Stewart
ORDSWF
Chicago O'Hare Intl
Fri 10/23
8:11 pm-11:39 am
2 stops14h 28m
New Windsor Stewart
Fri 10/30
5:39 pm-8:46 am
1 stop16h 07m
$395
Showing 1-10 of 21 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.
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Book flights to New Windsor if you plan to visit one of these locationsKingston
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