$109+ Cheap flights from New Windsor (SWF) to Chicago (CHI)
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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CHI
Oct 15 — Oct 221
Round-trip
1 adult, Economy
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Find cheap flights from Stewart to Chicago 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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Cheapest flights from Stewart to ChicagoExplore the most affordable flight options available from Stewart to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
Explore the most affordable flight options available from Stewart to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 11/226:48 pm -
1 stop18h 50m
Thu 12/35:00 am -
1 stop11h 59m
Deal found 9/11![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/66:49 pm -
1 stop19h 01m
Wed 12/96:15 am -
1 stop27h 11m
Deal found 9/14![Multiple Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/810:18 am -
1 stop30h 12m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/14![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/712:39 pm -
2 stops11h 20m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/14![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 12/106:49 pm -
1 stop19h 01m
Sun 12/135:00 am -
1 stop11h 59m
Deal found 9/10![Multiple Airlines logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/167:04 pm -
1 stop22h 59m
Tue 12/18:10 am -
2 stops26h 29m
Deal found 9/14![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 11/226:48 pm -
1 stop18h 50m
Tue 12/19:21 pm -
2 stops43h 38m
Deal found 9/11![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/2511:58 am -
2 stops22h 23m
Sat 10/318:00 am -
1 stop27h 08m
Deal found 9/11![Multiple Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/197:01 pm -
1 stop13h 50m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/10![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/1510:56 am -
1 stop22h 03m
Mon 10/1910:39 am -
1 stop6h 32m
Deal found 9/11![Multiple Airlines logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/1510:56 am -
1 stop22h 03m
Sun 10/181:12 pm -
2 stops27h 59m
Deal found 9/10![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/611:06 am -
1 stop8h 56m
Wed 12/99:23 pm -
2 stops19h 36m
Deal found 9/14![Multiple Airlines logo]()
$463
Best flights from Stewart to ChicagoDiscover carefully curated flight deals from Stewart to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
Discover carefully curated flight deals from Stewart to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 11/226:48 pm -
1 stop18h 50m
Thu 12/35:00 am -
1 stop11h 59m
Deal found 9/11![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/224:59 pm -
1 stop27h 07m
Mon 10/2610:44 am -
1 stop6h 27m
Deal found 9/12![Allegiant Air logo]()
$521
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/66:49 pm -
1 stop19h 01m
Wed 12/96:15 am -
1 stop27h 11m
Deal found 9/14![Multiple Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/810:18 am -
1 stop30h 12m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/14![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/167:04 pm -
1 stop22h 59m
Tue 12/18:10 am -
2 stops26h 29m
Deal found 9/14![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/197:01 pm -
1 stop13h 50m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/10![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/1712:39 pm -
2 stops19h 52m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/10![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 9/285:38 pm -
1 stop20h 13m
Sun 10/45:47 pm -
1 stop16h 32m
Deal found 9/12![Allegiant Air logo]()
$544
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 11/2112:39 pm -
2 stops13h 03m
Thu 12/35:00 am -
1 stop11h 59m
Deal found 9/13![Multiple Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/1510:56 am -
1 stop22h 03m
Mon 10/1910:39 am -
1 stop6h 32m
Deal found 9/11![Multiple Airlines logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/1311:09 am -
1 stop25h 45m
Sun 11/155:37 pm -
1 stop16h 52m
Deal found 9/14![Allegiant Air logo]()
$591
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/810:18 am -
1 stop30h 12m
Tue 10/137:44 pm -
2 stops36h 44m
Deal found 9/10![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 11/2311:29 am -
1 stop14h 13m
Thu 12/35:00 am -
1 stop11h 59m
Deal found 9/11![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 9/2711:13 am -
1 stop29h 47m
Thu 10/15:30 pm -
1 stop15h 59m
Deal found 9/12![Allegiant Air logo]()
$696
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/2612:39 pm -
2 stops12h 44m
Wed 9/307:11 am -
1 stop25h 27m
Deal found 9/11![Multiple Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/611:06 am -
1 stop8h 56m
Wed 12/99:23 pm -
2 stops19h 36m
Deal found 9/14![Multiple Airlines logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/86:45 pm -
1 stop25h 27m
Thu 10/159:40 am -
2 stops48h 59m
Deal found 9/10![Multiple Airlines logo]()
$509
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/2511:06 am -
1 stop9h 41m
Tue 12/12:04 pm -
2 stops20h 35m
Deal found 9/15![Multiple Airlines logo]()
$515
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 9/2710:56 am -
1 stop23h 36m
Fri 10/28:02 pm -
2 stops14h 37m
Deal found 9/12![Multiple Airlines logo]()
$566
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/2710:56 am -
1 stop23h 36m
Thu 10/15:30 pm -
1 stop15h 59m
Deal found 9/14![Multiple Airlines logo]()
$618
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 12/611:06 am -
1 stop8h 56m
Sat 12/129:41 pm -
2 stops19h 18m
Deal found 9/10![Multiple Airlines logo]()
$635
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/810:56 am -
1 stop22h 06m
Sun 10/116:37 pm -
1 stop15h 52m
Deal found 9/10![Multiple Airlines logo]()
$639
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/2710:56 am -
1 stop23h 36m
Mon 10/510:44 am -
1 stop6h 39m
Deal found 9/14![Multiple Airlines logo]()
$648
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/2511:06 am -
1 stop9h 41m
Thu 11/268:42 pm -
2 stops13h 54m
Deal found 9/14![Multiple Airlines logo]()
$726
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/127:01 pm -
2 stops20h 34m
Thu 10/159:18 am -
1 stop24h 11m
Deal found 9/14![Multiple Airlines logo]()
$797
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 11/2511:06 am -
1 stop9h 41m
Sun 11/298:42 pm -
2 stops13h 54m
Deal found 9/10![Multiple Airlines logo]()
$823
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 11/259:29 am -
1 stop11h 18m
Sat 11/288:42 pm -
1 stop10h 57m
Deal found 9/12![Multiple Airlines logo]()
$874
Last-minute flights from Stewart to ChicagoDiscover last-minute flight deals from Stewart to Chicago. Data last updated September 15, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Chicago. Data last updated September 15, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/411:48 am -
1 stop27h 57m
Wed 10/77:11 am -
1 stop25h 17m
Deal found 9/10![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/712:39 pm -
2 stops11h 20m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/14![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/810:18 am -
1 stop30h 12m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/14![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/810:18 am -
1 stop30h 12m
Tue 10/137:44 pm -
2 stops36h 44m
Deal found 9/10![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/86:45 pm -
1 stop25h 27m
Thu 10/159:40 am -
2 stops48h 59m
Deal found 9/10![Multiple Airlines logo]()
$509
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/1012:39 pm -
2 stops19h 52m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 9/10![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/1510:56 am -
1 stop22h 03m
Mon 10/1910:39 am -
1 stop6h 32m
Deal found 9/11![Multiple Airlines logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/1510:56 am -
1 stop22h 03m
Sun 10/181:12 pm -
2 stops27h 59m
Deal found 9/10![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/1712:39 pm -
2 stops19h 52m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/10![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/1811:53 am -
1 stop28h 37m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/13![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/197:01 pm -
1 stop13h 50m
Wed 10/218:04 am -
1 stop24h 44m
Deal found 9/10![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/2511:58 am -
2 stops22h 23m
Sat 10/318:00 am -
1 stop27h 08m
Deal found 9/11![Multiple Airlines logo]()
$299
One-way flights from Stewart to ChicagoSearch for one-way flight options from Stewart to Chicago. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
Search for one-way flight options from Stewart to Chicago. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 12/66:49 pm -
1 stop19h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/2910:38 am -
1 stop29h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 11/226:48 pm -
1 stop18h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/57:13 pm -
1 stop28h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 11/1512:00 pm -
2 stops30h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 11/1211:00 am -
1 stop29h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 11/167:04 pm -
2 stops24h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/2511:58 am -
2 stops22h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 11/1211:00 am -
2 stops31h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/3012:39 pm -
2 stops30h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/197:01 pm -
3 stops40h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/2511:58 am -
2 stops36h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$175
Find flight deals from Stewart to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Chicago (CHI). 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 15, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $269 (Kiwi.com) |
One-way from | $109 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $304 |
Cheapflights Fare Finder
Customize your flight search to find flights from Stewart to Chicago 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 15, 2026.
Use the filters below to find and compare flights from New Windsor to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Thu 10/29
10:38 am-3:37 pm
1 stop29h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$124
New WindsorChicago
SWF New Windsor Stewart - MDW Chicago Midway
SWFMDW
New Windsor Stewart
Sun 11/15
12:00 pm-5:47 pm
2 stops30h 47m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$152
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Wed 10/28
12:39 pm-6:45 pm
2 stops31h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Sun 11/15
12:00 pm-3:37 pm
1 stop28h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$180
New WindsorChicago
SWF New Windsor Stewart - MDW Chicago Midway
SWFMDW
New Windsor Stewart
Wed 10/28
12:39 pm-5:47 pm
2 stops30h 08m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$186
New WindsorChicago
SWF New Windsor Stewart - RFD Chicago Greater Rockford
SWFRFD
New Windsor Stewart
Thu 10/15
10:56 am-7:59 am
1 stop22h 03m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
Quickest round-trip
New WindsorChicago
SWF New Windsor Stewart - MDW Chicago Midway
SWFMDW
New Windsor Stewart
Sat 10/24
12:39 pm-11:43 pm
2 stops12h 04m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$190
New WindsorChicago
SWF New Windsor Stewart - RFD Chicago Greater Rockford
SWFRFD
New Windsor Stewart
Wed 10/28
12:39 pm-8:50 am
3 stops21h 11m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$190
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Mon 11/2
7:01 pm-6:16 pm
2 stops24h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$202
New WindsorChicago
SWF New Windsor Stewart - MDW Chicago Midway
SWFMDW
New Windsor Stewart
Mon 10/5
7:13 pm-5:46 pm
2 stops23h 33m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$203
Showing 1-10 of 57 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on New Windsor-Chicago flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on New Windsor-Chicago flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from New Windsor-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on New Windsor-Chicago 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 New Windsor-Chicago 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 Stewart to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Stewart with our price prediction graph.
SWF-CHI
SWF-ORD
SWF-RFD
SWF-MDW
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 New Windsor to Chicago
SWF-CHI
SWF-ORD
SWF-RFD
SWF-MDW
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Stewart to Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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