$105+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CHI
Sep 30 — Oct 71
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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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 Stewart to Chicago
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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 31, 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 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/28. 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
Wed 10/77:11 am -
1 stop25h 17m
Deal found 8/28![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 -
1 stop28h 32m
Sat 10/318:00 am -
1 stop27h 08m
Deal found 8/27![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 8/27. 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
Tue 11/37:28 pm -
2 stops37h 42m
Deal found 8/27![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 stop30h 28m
Tue 12/12:31 pm -
2 stops20h 08m
Deal found 8/27![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 8/27![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 stop24h 49m
Tue 12/12:31 pm -
2 stops20h 08m
Deal found 8/28![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 12/136:10 pm -
1 stop13h 42m
Deal found 8/27![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 10/168:48 pm -
1 stop12h 03m
Tue 10/207:44 pm -
2 stops37h 04m
Deal found 8/26![Multiple Airlines logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 8/27![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 10/79:34 am -
1 stop23h 42m
Deal found 8/27![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:46 pm -
1 stop16h 06m
Thu 1/75:26 pm -
1 stop14h 25m
Deal found 8/27![Allegiant Air logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:38 pm -
1 stop20h 13m
Fri 10/28:49 am -
1 stop10h 09m
Deal found 8/31![Allegiant Air logo]()
$534
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 31, 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 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/28. 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
Wed 10/77:11 am -
1 stop25h 17m
Deal found 8/28![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2211:01 am -
1 stop23h 54m
Sun 1/246:01 pm -
1 stop15h 10m
Deal found 8/28![Allegiant Air logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 8/27. 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
Tue 11/37:28 pm -
2 stops37h 42m
Deal found 8/27![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 8/27![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 8/28![Multiple Airlines logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:46 pm -
1 stop16h 06m
Thu 1/75:26 pm -
1 stop14h 25m
Deal found 8/28![Allegiant Air logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 12/136:10 pm -
1 stop13h 42m
Deal found 8/27![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 10/168:48 pm -
1 stop12h 03m
Tue 10/207:44 pm -
2 stops37h 04m
Deal found 8/26![Multiple Airlines logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:38 pm -
1 stop20h 13m
Fri 10/28:49 am -
1 stop10h 09m
Deal found 8/31![Allegiant Air logo]()
$534
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 8/28![Multiple Airlines logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 10/79:34 am -
1 stop23h 42m
Deal found 8/27![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 stop7h 19m
Sun 11/297:53 pm -
1 stop14h 16m
Deal found 8/28![Allegiant Air logo]()
$598
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:49 pm -
1 stop19h 01m
Sun 12/65:00 am -
1 stop11h 59m
Deal found 8/27![Multiple Airlines logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 12/185:46 pm -
1 stop24h 38m
Mon 1/49:50 am -
1 stop7h 21m
Deal found 8/29![Allegiant Air logo]()
$609
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 10/110:56 am -
1 stop13h 03m
Sat 10/37:11 am -
1 stop26h 47m
Deal found 8/29![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:46 pm -
1 stop24h 04m
Mon 1/49:50 am -
1 stop7h 21m
Deal found 8/27![Allegiant Air logo]()
$623
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:15 pm -
1 stop16h 26m
Sun 11/297:53 pm -
1 stop14h 16m
Deal found 8/31![Allegiant Air logo]()
$672
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:01 pm -
1 stop13h 50m
Fri 10/238:11 pm -
2 stops14h 28m
Deal found 8/31![Multiple Airlines logo]()
$462
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 9/1411:21 am -
2 stops27h 56m
Wed 9/163:50 pm -
1 stop17h 26m
Deal found 8/29![Multiple Airlines logo]()
$503
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 9/2511:06 am -
1 stop12h 53m
Sun 9/272:46 pm -
2 stops18h 45m
Deal found 8/29![Multiple Airlines logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 -
2 stops25h 31m
Mon 10/1210:39 am -
1 stop6h 32m
Deal found 8/29![Multiple Airlines logo]()
$871
This Kiwi.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2011:06 am -
1 stop8h 56m
Thu 12/318:07 pm -
2 stops14h 29m
Deal found 8/30![Multiple Airlines logo]()
$1,204
This Kiwi.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2711:06 am -
1 stop8h 56m
Fri 1/18:07 pm -
2 stops14h 32m
Deal found 8/30![Multiple Airlines logo]()
$1,828
Last-minute flights from Stewart to ChicagoDiscover last-minute flight deals from Stewart to Chicago. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Chicago. Data last updated August 31, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/310:33 am -
1 stop13h 35m
Tue 9/89:10 pm -
2 stops36h 06m
Deal found 8/28![Multiple Airlines logo]()
$495
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 -
2 stops34h 32m
Sun 9/68:05 am -
1 stop9h 35m
Deal found 8/27![Multiple Airlines logo]()
$450
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 9/610:33 am -
1 stop13h 35m
Fri 9/113:50 pm -
2 stops18h 49m
Deal found 8/29![Multiple Airlines logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 9/1411:21 am -
2 stops27h 56m
Wed 9/163:50 pm -
1 stop17h 26m
Deal found 8/29![Multiple Airlines logo]()
$503
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 9/1811:06 am -
1 stop12h 53m
Sun 9/273:50 pm -
1 stop17h 41m
Deal found 8/27![Multiple Airlines logo]()
$475
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 9/2511:06 am -
1 stop12h 53m
Sun 9/272:46 pm -
2 stops18h 45m
Deal found 8/29![Multiple Airlines logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 stop24h 24m
Thu 10/13:50 pm -
2 stops18h 46m
Deal found 8/27![Multiple Airlines logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:38 pm -
1 stop20h 13m
Fri 10/28:49 am -
1 stop10h 09m
Deal found 8/31![Allegiant Air logo]()
$534
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 31, 2026.
Search for one-way flight options from Stewart to Chicago. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/29. 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
Deal found 8/29![Multiple Airlines logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 8/28![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 11/511:00 am -
1 stop29h 37m
Deal found 8/27![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 -
1 stop30h 12m
Deal found 8/27![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:00 am -
1 stop29h 37m
Deal found 8/30![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 stops31h 03m
Deal found 8/26![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 8/28![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:39 pm -
3 stops27h 24m
Deal found 8/31![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/1111:06 am -
2 stops31h 45m
Deal found 8/28![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 -
3 stops37h 30m
Deal found 8/28![Multiple Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/29. 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
Deal found 8/29![Allegiant Air logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 10/312:39 pm -
3 stops21h 39m
Deal found 8/28![Multiple Airlines logo]()
$171
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 31, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $219 (Kiwi.com) |
One-way from | $105 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $299 |
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 August 31, 2026.
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Route
Depart
Return
Cheapest round-trip
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Thu 10/1
10:28 am-2:45 pm
1 stop29h 17m
Chicago O'Hare Intl
Wed 10/7
7:11 am-9:28 am
1 stop25h 17m
$228
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
Tue 11/3
7:28 pm-10:10 am
2 stops37h 42m
$275
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Sun 10/4
11:48 am-2:45 pm
1 stop27h 57m
Chicago O'Hare Intl
Wed 10/7
7:11 am-9:28 am
1 stop25h 17m
$305
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Sun 10/18
11:53 am-3:30 pm
1 stop28h 37m
Chicago O'Hare Intl
Wed 10/21
8:04 am-9:48 am
1 stop24h 44m
$312
New WindsorChicago
SWF New Windsor Stewart - RFD Chicago Greater Rockford
SWFRFD
New Windsor Stewart
Fri 1/22
11:01 am-9:55 am
1 stop23h 54m
Chicago Greater Rockford
Sun 1/24
6:01 pm-10:11 am
1 stop15h 10m
$342
New WindsorChicago
SWF New Windsor Stewart - MDW Chicago Midway
SWFMDW
New Windsor Stewart
Thu 12/10
11:06 am-7:02 pm
1 stop8h 56m
Chicago Midway
Sun 12/13
6:10 pm-8:52 am
1 stop13h 42m
$358
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Fri 10/16
8:48 pm-7:51 am
1 stop12h 03m
Chicago O'Hare Intl
Tue 10/20
7:44 pm-9:48 am
2 stops37h 04m
$364
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Thu 12/10
6:49 pm-12:50 pm
1 stop19h 01m
Chicago O'Hare Intl
Sun 12/13
5:00 am-5:59 pm
1 stop11h 59m
$374
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
Wed 10/7
9:34 am-10:16 am
1 stop23h 42m
$387
New WindsorChicago
SWF New Windsor Stewart - ORD Chicago O'Hare Intl
SWFORD
New Windsor Stewart
Thu 12/3
6:49 pm-12:50 pm
1 stop19h 01m
Chicago O'Hare Intl
Sun 12/6
5:00 am-5:59 pm
1 stop11h 59m
$387
Showing 1-10 of 52 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
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Related info for your journey
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Traveling to a place near Chicago?
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Lansing
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Hammond
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Porter
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