$95+ Cheap flights from Westchester County 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Mar 14 — Mar 211
1 adult, Economy
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Find cheap flights from Westchester County 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 Westchester County to Chicago
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Cheapest flights from Westchester County to ChicagoExplore the most affordable flight options available from Westchester County to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
Explore the most affordable flight options available from Westchester County to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 2/2312:08 pm
HPN
- ORD
1 stop12h 29m
Multiple Airlines
Wed 3/48:30 am
ORD
- HPN
2 stops25h 58m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 2/2712:08 pm
HPN
- ORD
1 stop12h 29m
Multiple Airlines
Mon 3/23:50 pm
ORD
- HPN
2 stops18h 38m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 3/912:08 pm
HPN
- ORD
2 stops12h 30m
Multiple Airlines
Thu 3/1212:34 pm
ORD
- HPN
1 stop21h 54m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 2/2312:08 pm
HPN
- ORD
1 stop12h 29m
Multiple Airlines
Tue 2/248:42 pm
ORD
- HPN
2 stops15h 05m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 3/1612:08 pm
HPN
- ORD
2 stops12h 30m
Multiple Airlines
Thu 3/1912:34 pm
ORD
- HPN
1 stop21h 54m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 4/1712:08 pm
HPN
- ORD
1 stop12h 08m
Multiple Airlines
Tue 4/218:58 am
ORD
- HPN
2 stops26h 49m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 2/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/173:01 pm
HPN
- ORD
2 stops15h 22m
American Airlines
Sat 4/188:08 am
ORD
- HPN
Nonstop2h 19m
American Airlines
Deal found 2/8![American Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 5/86:09 pm
HPN
- ORD
1 stop6h 07m
Multiple Airlines
Wed 5/277:35 pm
ORD
- HPN
2 stops16h 05m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 5/148:00 am
HPN
- ORD
1 stop11h 43m
Multiple Airlines
Mon 5/186:57 am
ORD
- HPN
2 stops27h 30m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$328
This KAYAK deal was found by Cheapflights users on 2/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:30 pm
HPN
- ORD
2 stops13h 06m
American Airlines
Sat 2/288:14 am
ORD
- HPN
Nonstop2h 15m
American Airlines
Deal found 2/9![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1412:00 pm
HPN
- ORD
Nonstop2h 43m
American Airlines
Sat 3/143:59 pm
ORD
- HPN
2 stops18h 00m
American Airlines
Deal found 2/10![American Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 4/1712:08 pm
HPN
- ORD
1 stop12h 08m
Multiple Airlines
Mon 4/201:35 pm
ORD
- HPN
2 stops29h 55m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$343
Best flights from Westchester County to ChicagoDiscover carefully curated flight deals from Westchester County to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
Discover carefully curated flight deals from Westchester County to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
This KAYAK deal was found by Cheapflights users on 2/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:30 pm
HPN
- ORD
2 stops13h 06m
American Airlines
Sat 2/288:14 am
ORD
- HPN
Nonstop2h 15m
American Airlines
Deal found 2/9![American Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:59 pm
HPN
- ORD
1 stop7h 02m
Delta
Wed 7/87:10 am
ORD
- HPN
1 stop3h 34m
Delta
Deal found 2/9![Delta logo]()
$375
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/112:35 pm
HPN
- MDW
1 stop6h 19m
Delta
Sat 4/49:30 am
MDW
- HPN
1 stop6h 05m
Delta
Deal found 2/9![Delta logo]()
$385
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:30 am
HPN
- ORD
Nonstop2h 50m
American Airlines
Tue 3/3112:50 pm
ORD
- HPN
Nonstop2h 09m
American Airlines
Deal found 2/11![American Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 2/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/164:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Sat 5/239:23 am
MDW
- HPN
1 stop6h 13m
Delta
Deal found 2/10![Delta logo]()
$385
This American Airlines deal was found by Cheapflights users on 2/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3012:00 pm
HPN
- ORD
Nonstop2h 43m
American Airlines
Sat 5/28:08 am
ORD
- HPN
Nonstop2h 19m
American Airlines
Deal found 2/12![American Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:00 pm
HPN
- ORD
Nonstop2h 43m
American Airlines
Mon 4/202:09 pm
ORD
- HPN
Nonstop2h 17m
American Airlines
Deal found 2/11![American Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:12 pm
HPN
- ORD
1 stop4h 32m
Delta
Sat 3/215:30 am
ORD
- HPN
1 stop5h 33m
Delta
Deal found 2/9![Delta logo]()
$405
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:30 am
HPN
- ORD
Nonstop2h 50m
American Airlines
Sat 3/216:38 pm
ORD
- HPN
Nonstop2h 21m
American Airlines
Deal found 2/10![American Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:29 pm
HPN
- MDW
1 stop6h 59m
Delta
Sat 5/210:43 am
MDW
- HPN
1 stop6h 31m
Delta
Deal found 2/12![Delta logo]()
$409
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:00 am
HPN
- ORD
Nonstop2h 49m
American Airlines
Tue 4/1412:42 pm
ORD
- HPN
1 stop6h 45m
American Airlines
Deal found 2/10![American Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 2/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:15 pm
HPN
- ORD
1 stop7h 39m
Delta
Sun 4/127:10 am
ORD
- HPN
1 stop3h 43m
Delta
Deal found 2/8![Delta logo]()
$409
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:01 pm
HPN
- ORD
1 stop7h 20m
American Airlines
Mon 5/112:09 pm
ORD
- HPN
Nonstop2h 17m
American Airlines
Deal found 2/11![American Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 2/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/912:35 pm
HPN
- ORD
1 stop5h 08m
Delta
Sat 4/117:10 am
ORD
- HPN
1 stop3h 33m
Delta
Deal found 2/8![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 2/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2712:45 pm
HPN
- MDW
1 stop6h 46m
Delta
Sat 7/46:00 am
MDW
- HPN
1 stop5h 14m
Delta
Deal found 2/11![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 2/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:30 pm
HPN
- MDW
1 stop6h 44m
Delta
Sun 5/319:22 am
MDW
- HPN
1 stop5h 27m
Delta
Deal found 2/11![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:17 pm
HPN
- MDW
1 stop6h 11m
Delta
Mon 5/46:00 am
MDW
- HPN
1 stop5h 02m
Delta
Deal found 2/9![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 2/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/174:29 pm
HPN
- MDW
1 stop6h 59m
Delta
Tue 4/219:27 am
MDW
- HPN
1 stop5h 22m
Delta
Deal found 2/10![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2512:35 pm
HPN
- MDW
1 stop6h 19m
Delta
Sun 3/299:35 am
MDW
- HPN
1 stop5h 14m
Delta
Deal found 2/9![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1110:27 am
HPN
- MDW
1 stop7h 55m
Delta
Mon 3/169:35 am
MDW
- HPN
1 stop5h 14m
Delta
Deal found 2/9![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 2/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:17 pm
HPN
- MDW
1 stop6h 11m
Delta
Mon 4/2010:43 am
MDW
- HPN
1 stop6h 31m
Delta
Deal found 2/11![Delta logo]()
$419
Last-minute flights from Westchester County to ChicagoDiscover last-minute flight deals from Westchester County to Chicago. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Westchester County to Chicago. Data last updated February 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 2/2312:08 pm
HPN
- ORD
1 stop12h 29m
Multiple Airlines
Wed 3/48:30 am
ORD
- HPN
2 stops25h 58m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 2/2312:08 pm
HPN
- ORD
1 stop12h 29m
Multiple Airlines
Tue 2/248:42 pm
ORD
- HPN
2 stops15h 05m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 2/2712:08 pm
HPN
- ORD
1 stop12h 29m
Multiple Airlines
Mon 3/23:50 pm
ORD
- HPN
2 stops18h 38m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$247
This KAYAK deal was found by Cheapflights users on 2/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:30 pm
HPN
- ORD
2 stops13h 06m
American Airlines
Sat 2/288:14 am
ORD
- HPN
Nonstop2h 15m
American Airlines
Deal found 2/9![American Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 3/612:08 pm
HPN
- ORD
2 stops24h 08m
Multiple Airlines
Sun 3/812:34 pm
ORD
- HPN
1 stop21h 54m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 3/912:08 pm
HPN
- ORD
2 stops12h 30m
Multiple Airlines
Thu 3/1212:34 pm
ORD
- HPN
1 stop21h 54m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$253
This American Airlines deal was found by Cheapflights users on 2/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:29 pm
HPN
- ORD
Nonstop2h 48m
American Airlines
Wed 4/16:38 pm
ORD
- HPN
Nonstop2h 21m
American Airlines
Deal found 2/9![American Airlines logo]()
$355
This American Airlines deal was found by Cheapflights users on 2/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:00 am
HPN
- ORD
1 stop5h 57m
American Airlines
Tue 3/318:14 am
ORD
- HPN
Nonstop2h 15m
American Airlines
Deal found 2/9![American Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 2/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1112:48 pm
HPN
- ORD
1 stop7h 05m
Delta
Tue 3/315:30 am
ORD
- HPN
1 stop7h 59m
Delta
Deal found 2/9![Delta logo]()
$375
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1412:00 pm
HPN
- ORD
Nonstop2h 43m
American Airlines
Sat 3/143:59 pm
ORD
- HPN
2 stops18h 00m
American Airlines
Deal found 2/10![American Airlines logo]()
$338
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:00 am
HPN
- ORD
2 stops24h 36m
American Airlines
Sun 3/158:14 am
ORD
- HPN
Nonstop2h 15m
American Airlines
Deal found 2/10![American Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 3/1612:08 pm
HPN
- ORD
2 stops12h 30m
Multiple Airlines
Thu 3/1912:34 pm
ORD
- HPN
1 stop21h 54m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$279
One-way flights from Westchester County to ChicagoSearch for one-way flight options from Westchester County to Chicago. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
Search for one-way flight options from Westchester County to Chicago. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 5/116:09 pm
HPN
- ORD
1 stop6h 07m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 2/2312:08 pm
HPN
- ORD
1 stop12h 29m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 4/81:27 pm
HPN
- ORD
2 stops11h 55m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 3/912:08 pm
HPN
- ORD
2 stops32h 39m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 5/108:00 am
HPN
- ORD
2 stops40h 58m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 2/2312:08 pm
HPN
- MDW
2 stops31h 59m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 3/212:08 pm
HPN
- MDW
3 stops31h 59m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 3/41:27 pm
HPN
- MDW
2 stops27h 49m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 3/312:08 pm
HPN
- MDW
3 stops31h 59m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 3/1012:08 pm
HPN
- MDW
3 stops23h 17m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 5/148:00 am
HPN
- MDW
2 stops15h 19m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 3/18:00 am
HPN
- MDW
3 stops31h 29m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$233
Find flight deals from Westchester County to Chicago
Keep the following information in mind while searching for Westchester County to Chicago flight deals. Data was last updated February 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $236 (Kiwi.com) |
One-way from | $95 (Kiwi.com) |
Popular in | August |
Cheapest in | January |
Average price | $206 |
Cheapflights Fare Finder
Customize your flight search to find flights from Westchester County 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 February 12, 2026.
Use the filters below to find and compare flights from Westchester County to Chicago that are best for you.
Fly from
Westchester County
Fly to
Chicago
Route
Depart
Return
Price
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Fri 2/27
5:30 pm-5:36 am
2 stops13h 06m
Chicago O'Hare Intl
Sat 2/28
8:14 am-11:29 am
Nonstop2h 15m
$334
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Wed 7/1
12:59 pm-7:01 pm
1 stop7h 02m
Chicago O'Hare Intl
Wed 7/8
7:10 am-11:44 am
1 stop3h 34m
$375
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Wed 4/1
12:35 pm-5:54 pm
1 stop6h 19m
Chicago Midway
Sat 4/4
9:30 am-4:35 pm
1 stop6h 05m
$385
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Wed 3/11
6:30 am-8:20 am
Nonstop2h 50m
Chicago O'Hare Intl
Tue 3/31
12:50 pm-3:59 pm
Nonstop2h 09m
$385
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Sat 5/16
4:29 pm-9:09 pm
1 stop5h 40m
Chicago Midway
Sat 5/23
9:23 am-4:36 pm
1 stop6h 13m
$385
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Thu 4/30
12:00 pm-1:43 pm
Nonstop2h 43m
Chicago O'Hare Intl
Sat 5/2
8:08 am-11:27 am
Nonstop2h 19m
$389
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Sat 4/18
12:00 pm-1:43 pm
Nonstop2h 43m
Chicago O'Hare Intl
Mon 4/20
2:09 pm-5:26 pm
Nonstop2h 17m
$389
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Sun 3/15
6:30 am-8:20 am
Nonstop2h 50m
Chicago O'Hare Intl
Sat 3/21
6:38 pm-9:59 pm
Nonstop2h 21m
$389
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Fri 4/10
7:00 am-8:49 am
Nonstop2h 49m
Chicago O'Hare Intl
Tue 4/14
12:42 pm-8:27 pm
1 stop6h 45m
$399
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Sat 5/9
3:01 pm-9:21 pm
1 stop7h 20m
Chicago O'Hare Intl
Mon 5/11
2:09 pm-5:26 pm
Nonstop2h 17m
$399
Showing 1-10 of 34 results
Best time to book a flight from Westchester County to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Westchester County with our price prediction graph.
HPN-ORD
HPN-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 Westchester County to Chicago
zzREU-CHI
HPN-ORD
HPN-MDW
What is the cheapest month to book a flight from Westchester County to Chicago?
Currently, February is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $233). Flying from Westchester County to Chicago in October is currently the most expensive (average of $380). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from REU to CHI?
Find hourly flight availability from Westchester County to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 12, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Westchester County to Chicago as you normally would.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 12, 2026.
See what other customers who have flown with Delta and American Airlines from Westchester County to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Comfort
7.9
Food
7.2
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Comfort
7.9
Food
7.2
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Entertainment
7.8
Overall
7.9
Boarding
8.1
Crew
8.5
Comfort
7.9
Food
7.2
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Related info for your journey
Find useful and relevant information for your journey from Westchester County 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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Alternative routes for Westchester County to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 12, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Westchester County to Chicago by cabin class
Find flights from Westchester County to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Westchester County and Chicago flights
Browse other Westchester County and Chicago flight options. Last updated on February 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Westchester County to Chicago
Discover the top airline that operate flights from Westchester County to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$371 | Average$482 | FlexibilityNo cancel fee | On-time71% |