$88+ Cheap flights from New Windsor (SWF) to Chicago (CHI)
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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CHI
Sep 18 — Sep 251
Round-trip
1 adult, Economy
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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 August 19, 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 August 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/110:28 am -
2 stops15h 17m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 8/17![Multiple Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/28:48 pm -
1 stop27h 11m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 8/17![Multiple Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 46m
Sat 10/314:44 pm -
1 stop17h 32m
Deal found 8/17![Multiple Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/110:28 am -
2 stops15h 17m
Sat 10/108:04 am -
1 stop25h 59m
Deal found 8/17![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 -
2 stops24h 10m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 8/17![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/28:48 pm -
1 stop27h 11m
Sat 10/108:04 am -
1 stop25h 59m
Deal found 8/17![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 -
2 stops24h 10m
Sat 10/108:04 am -
1 stop25h 59m
Deal found 8/17![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Sun 10/1110:56 am -
1 stop21h 35m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 8/15![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 -
2 stops22h 32m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 8/17![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/410:56 am -
1 stop23h 58m
Thu 10/159:40 am -
2 stops48h 59m
Deal found 8/17![Multiple Airlines logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/410:56 am -
1 stop23h 58m
Fri 10/98:02 pm -
2 stops38h 01m
Deal found 8/17![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/410:56 am -
1 stop23h 58m
Wed 10/149:34 am -
1 stop23h 42m
Deal found 8/17![Multiple Airlines logo]()
$389
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 August 19, 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 August 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/28:48 pm -
1 stop27h 11m
Sat 10/108:04 am -
1 stop25h 59m
Deal found 8/17![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 1/710:53 am -
1 stop22h 59m
Sun 1/105:06 pm -
1 stop14h 45m
Deal found 8/14![Allegiant Air logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/1010:56 am -
1 stop13h 03m
Tue 9/157:28 pm -
2 stops37h 48m
Deal found 8/14![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/28:48 pm -
1 stop27h 11m
Tue 10/136:00 am -
2 stops28h 39m
Deal found 8/17![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 -
2 stops26h 24m
Sat 10/314:44 pm -
1 stop17h 32m
Deal found 8/17![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Sun 10/1111:53 am -
2 stops13h 33m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 8/15![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 8/307:31 pm -
1 stop18h 19m
Thu 9/38:14 am -
1 stop9h 26m
Deal found 8/14![Multiple Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/17:36 pm -
1 stop24h 36m
Mon 10/1210:39 am -
1 stop6h 32m
Deal found 8/17![Allegiant Air logo]()
$585
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/410:56 am -
1 stop23h 58m
Thu 10/159:40 am -
2 stops48h 59m
Deal found 8/17![Multiple Airlines logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 11/1210:56 am -
1 stop13h 54m
Mon 11/164:44 pm -
2 stops41h 55m
Deal found 8/17![Multiple Airlines logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/410:36 am -
1 stop13h 32m
Mon 9/79:10 pm -
2 stops37h 29m
Deal found 8/16![Multiple Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Thu 9/37:30 pm -
1 stop18h 20m
Tue 9/85:29 pm -
2 stops17h 10m
Deal found 8/15![Multiple Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 8/17. 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
Fri 10/98:11 pm -
2 stops14h 28m
Deal found 8/17![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/1010:56 am -
1 stop13h 03m
Sun 9/133:50 pm -
1 stop17h 41m
Deal found 8/19![Multiple Airlines logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/17:36 pm -
1 stop24h 36m
Wed 10/1411:04 am -
2 stops21h 24m
Deal found 8/17![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/211:19 am -
1 stop24h 33m
Wed 10/149:34 am -
1 stop23h 42m
Deal found 8/17![Multiple Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/28:48 pm -
2 stops22h 03m
Thu 10/159:18 am -
1 stop24h 11m
Deal found 8/17![Multiple Airlines logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/28:48 pm -
2 stops22h 03m
Sun 10/1111:38 am -
1 stop22h 51m
Deal found 8/17![Multiple Airlines logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 11/1210:56 am -
2 stops11h 57m
Sun 11/1510:42 am -
1 stop23h 47m
Deal found 8/14![Multiple Airlines logo]()
$475
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/410:56 am -
1 stop23h 58m
Sun 10/116:37 pm -
1 stop15h 52m
Deal found 8/17![Multiple Airlines logo]()
$476
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 -
2 stops13h 47m
Thu 11/1210:12 am -
1 stop23h 07m
Deal found 8/17![Multiple Airlines logo]()
$489
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/211:19 am -
1 stop24h 33m
Mon 10/1210:39 am -
2 stops48h 00m
Deal found 8/17![Multiple Airlines logo]()
$493
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Fri 12/187:15 pm -
1 stop15h 40m
Mon 1/49:50 am -
2 stops48h 49m
Deal found 8/15![Multiple Airlines logo]()
$563
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 12/1011:06 am -
1 stop8h 56m
Sun 12/138:07 pm -
2 stops14h 29m
Deal found 8/18![Multiple Airlines logo]()
$689
Last-minute flights from Stewart to ChicagoDiscover last-minute flight deals from Stewart to Chicago. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Chicago. Data last updated August 19, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 8/307:31 pm -
2 stops37h 22m
Thu 9/38:14 am -
1 stop9h 26m
Deal found 8/14![Multiple Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/111:48 am -
1 stop12h 20m
Sun 9/68:05 am -
1 stop9h 35m
Deal found 8/19![Multiple Airlines logo]()
$427
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Thu 9/37:30 pm -
1 stop18h 20m
Tue 9/85:29 pm -
2 stops17h 10m
Deal found 8/15![Multiple Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/37:30 pm -
1 stop18h 20m
Sun 9/68:05 am -
1 stop9h 35m
Deal found 8/14![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/1010:56 am -
1 stop13h 03m
Tue 9/157:28 pm -
2 stops37h 48m
Deal found 8/14![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/1010:56 am -
1 stop13h 03m
Sun 9/133:50 pm -
2 stops18h 46m
Deal found 8/19![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/1710:56 am -
1 stop13h 03m
Sat 9/194:35 pm -
2 stops16h 41m
Deal found 8/18![Multiple Airlines logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 stops11h 20m
Wed 10/148:04 am -
1 stop24h 24m
Deal found 8/17![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 stops11h 20m
Sat 10/108:04 am -
1 stop25h 59m
Deal found 8/17![Multiple Airlines logo]()
$331
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 August 19, 2026.
Search for one-way flight options from Stewart to Chicago. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 -
1 stop28h 24m
Deal found 8/18![Multiple Airlines logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 10/110:28 am -
1 stop29h 17m
Deal found 8/18![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/267:01 pm -
1 stop29h 49m
Deal found 8/14![Multiple Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/1510:18 am -
2 stops24h 03m
Deal found 8/14![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 10/1811:53 am -
1 stop28h 43m
Deal found 8/14![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/2210:38 am -
1 stop29h 58m
Deal found 8/17![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 stops50h 28m
Deal found 8/16![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/212:05 pm -
2 stops11h 42m
Deal found 8/14![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 8/3111:56 am -
2 stops35h 51m
Deal found 8/14![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/110:28 am -
2 stops32h 23m
Deal found 8/17![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/912:39 pm -
3 stops27h 24m
Deal found 8/18![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/2312:39 pm -
3 stops27h 24m
Deal found 8/18![Multiple Airlines logo]()
$141
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 August 19, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $223 (Kiwi.com) |
One-way from | $88 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $296 |
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 2,558,603 searches. Data last updated August 19, 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
Fri 10/2
8:48 pm-10:59 pm
1 stop27h 11m
Chicago O'Hare Intl
Sat 10/10
8:04 am-11:03 am
1 stop25h 59m
$256
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Thu 9/10
10:56 am-10:59 pm
1 stop13h 03m
Chicago O'Hare Intl
Tue 9/15
7:28 pm-10:16 am
2 stops37h 48m
$306
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Fri 10/2
8:48 pm-10:59 pm
1 stop27h 11m
Chicago O'Hare Intl
Tue 10/13
6:00 am-11:39 am
2 stops28h 39m
$311
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Thu 10/29
10:38 am-12:02 pm
2 stops26h 24m
Chicago O'Hare Intl
Sat 10/31
4:44 pm-11:16 am
1 stop17h 32m
$322
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Sun 10/11
11:53 am-12:26 am
2 stops13h 33m
Chicago O'Hare Intl
Wed 10/14
8:04 am-9:28 am
1 stop24h 24m
$334
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Sun 8/30
7:31 pm-12:50 pm
1 stop18h 19m
Chicago O'Hare Intl
Thu 9/3
8:14 am-6:40 pm
1 stop9h 26m
$356
New WindsorChicago
SWF New Windsor Stewart - RFD Chicago Greater Rockford
SWFRFD
New Windsor Stewart
Sun 10/4
10:56 am-9:54 am
1 stop23h 58m
Chicago Greater Rockford
Thu 10/15
9:40 am-11:39 am
2 stops48h 59m
$382
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Thu 11/12
10:56 am-11:50 pm
1 stop13h 54m
Chicago O'Hare Intl
Mon 11/16
4:44 pm-11:39 am
2 stops41h 55m
$396
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Fri 9/4
10:36 am-11:08 pm
1 stop13h 32m
Chicago O'Hare Intl
Mon 9/7
9:10 pm-11:39 am
2 stops37h 29m
$397
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Thu 9/3
7:30 pm-12:50 pm
1 stop18h 20m
Chicago O'Hare Intl
Tue 9/8
5:29 pm-11:39 am
2 stops17h 10m
$397
Showing 1-10 of 54 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
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Hammond
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Porter
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