$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 19 — Mar 261
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Westchester County to Chicago
Cheapest
Best
Last-minute
One-way
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 17, 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 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 5/112:08 pm
HPN
- ORD
1 stop12h 08m
Multiple Airlines
Sun 5/31:12 pm
ORD
- HPN
1 stop21h 16m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:09 pm
HPN
- ORD
1 stop6h 07m
Multiple Airlines
Tue 5/191:40 pm
ORD
- HPN
2 stops20h 37m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:09 pm
HPN
- ORD
1 stop6h 07m
Multiple Airlines
Mon 5/186:57 am
ORD
- HPN
2 stops27h 30m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 4/1712:08 pm
HPN
- ORD
1 stop12h 08m
Multiple Airlines
Mon 4/206:57 am
ORD
- HPN
2 stops27h 31m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1712:08 pm
HPN
- ORD
1 stop12h 08m
Multiple Airlines
Sun 4/1910:25 am
ORD
- HPN
2 stops24h 03m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 3/212:08 pm
HPN
- ORD
1 stop12h 29m
Multiple Airlines
Wed 3/412:44 pm
ORD
- HPN
2 stops21h 44m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 4/2412:08 pm
HPN
- ORD
2 stops12h 02m
Multiple Airlines
Sun 4/261:12 pm
ORD
- HPN
1 stop21h 16m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Mon 3/231:10 pm
HPN
- ORD
2 stops23h 40m
Multiple Airlines
Sun 3/2912:34 pm
ORD
- HPN
1 stop21h 54m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Mon 4/2012:08 pm
HPN
- ORD
1 stop12h 08m
Multiple Airlines
Tue 4/217:49 pm
ORD
- HPN
2 stops15h 58m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 2/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:45 pm
HPN
- MDW
1 stop9h 24m
Delta
Tue 5/199:23 am
MDW
- HPN
1 stop6h 13m
Delta
Deal found 2/14![Delta logo]()
$346
This Delta deal was found by Cheapflights users on 2/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
HPN
- MDW
1 stop7h 02m
Delta
Tue 3/246:00 am
MDW
- HPN
1 stop7h 29m
Delta
Deal found 2/15![Delta logo]()
$375
This Delta deal was found by Cheapflights users on 2/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:54 pm
HPN
- MDW
1 stop16h 02m
Delta
Sun 4/199:27 am
MDW
- HPN
1 stop5h 22m
Delta
Deal found 2/15![Delta logo]()
$380
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 17, 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 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:09 pm
HPN
- ORD
1 stop6h 07m
Multiple Airlines
Mon 5/186:57 am
ORD
- HPN
2 stops27h 30m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 2/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:45 pm
HPN
- MDW
1 stop9h 24m
Delta
Tue 5/199:23 am
MDW
- HPN
1 stop6h 13m
Delta
Deal found 2/14![Delta logo]()
$346
This American Airlines deal was found by Cheapflights users on 2/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:00 pm
HPN
- ORD
Nonstop2h 43m
American Airlines
Tue 5/196:36 pm
ORD
- HPN
Nonstop2h 23m
American Airlines
Deal found 2/14![American Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1012:08 pm
HPN
- ORD
1 stop6h 08m
Multiple Airlines
Tue 4/145:01 am
ORD
- HPN
2 stops30h 46m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$368
This American Airlines deal was found by Cheapflights users on 2/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:30 am
HPN
- ORD
Nonstop2h 50m
American Airlines
Wed 4/155:00 am
ORD
- HPN
1 stop7h 00m
American Airlines
Deal found 2/15![American Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 2/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
HPN
- MDW
1 stop7h 02m
Delta
Tue 3/246:00 am
MDW
- HPN
1 stop7h 29m
Delta
Deal found 2/15![Delta logo]()
$375
This Delta deal was found by Cheapflights users on 2/15. 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 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
Wed 4/156:00 am
MDW
- HPN
1 stop5h 00m
Delta
Deal found 2/15![Delta logo]()
$375
This American Airlines deal was found by Cheapflights users on 2/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1012:00 pm
HPN
- ORD
Nonstop2h 43m
American Airlines
Tue 3/318:14 am
ORD
- HPN
Nonstop2h 15m
American Airlines
Deal found 2/15![American Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 2/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2112:45 pm
HPN
- MDW
1 stop6h 46m
Delta
Tue 7/289:30 am
MDW
- HPN
1 stop6h 03m
Delta
Deal found 2/16![Delta logo]()
$375
This American Airlines deal was found by Cheapflights users on 2/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:00 am
HPN
- ORD
Nonstop2h 49m
American Airlines
Mon 4/206:36 pm
ORD
- HPN
Nonstop2h 23m
American Airlines
Deal found 2/14![American Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 2/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/43:15 pm
HPN
- ORD
1 stop7h 19m
Delta
Wed 7/87:10 am
ORD
- HPN
1 stop3h 34m
Delta
Deal found 2/17![Delta logo]()
$375
This American Airlines deal was found by Cheapflights users on 2/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:59 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
Mon 5/116:36 pm
ORD
- HPN
Nonstop2h 23m
American Airlines
Deal found 2/16![American Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 2/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
HPN
- ORD
1 stop8h 14m
Delta
Sat 4/187:00 am
ORD
- HPN
1 stop3h 49m
Delta
Deal found 2/15![Delta logo]()
$375
This Delta deal was found by Cheapflights users on 2/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2712:45 pm
HPN
- ORD
1 stop4h 51m
Delta
Sat 7/49:30 am
ORD
- HPN
1 stop6h 10m
Delta
Deal found 2/14![Delta logo]()
$375
This Delta deal was found by Cheapflights users on 2/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:15 pm
HPN
- MDW
1 stop18h 27m
Delta
Tue 5/199:22 am
MDW
- HPN
1 stop5h 27m
Delta
Deal found 2/14![Delta logo]()
$380
This Delta deal was found by Cheapflights users on 2/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:54 pm
HPN
- MDW
1 stop16h 02m
Delta
Sun 4/199:27 am
MDW
- HPN
1 stop5h 22m
Delta
Deal found 2/15![Delta logo]()
$380
This Delta deal was found by Cheapflights users on 2/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:54 pm
HPN
- ORD
1 stop14h 43m
Delta
Sun 4/1911:00 am
ORD
- HPN
1 stop3h 49m
Delta
Deal found 2/15![Delta logo]()
$380
This Delta deal was found by Cheapflights users on 2/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/145:15 pm
HPN
- MDW
1 stop6h 16m
Delta
Sat 3/219:30 am
MDW
- HPN
1 stop6h 05m
Delta
Deal found 2/17![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 2/14. 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 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 stop7h 32m
Delta
Deal found 2/14![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 2/14. 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 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 2/14![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 2/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:29 pm
HPN
- MDW
1 stop7h 02m
Delta
Mon 3/309:35 am
MDW
- HPN
1 stop5h 14m
Delta
Deal found 2/16![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 2/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:30 pm
HPN
- MDW
1 stop6h 44m
Delta
Mon 5/189:22 am
MDW
- HPN
1 stop5h 27m
Delta
Deal found 2/14![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 2/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1812:35 pm
HPN
- MDW
1 stop6h 19m
Delta
Mon 3/239:30 am
MDW
- HPN
1 stop6h 07m
Delta
Deal found 2/16![Delta logo]()
$409
Last-minute flights from Westchester County to ChicagoDiscover last-minute flight deals from Westchester County to Chicago. Data last updated February 17, 2026 and is based on user searches.
Discover last-minute flight deals from Westchester County to Chicago. Data last updated February 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2712:08 pm
HPN
- ORD
1 stop12h 29m
Multiple Airlines
Tue 3/38:42 pm
ORD
- HPN
2 stops15h 05m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 3/212:08 pm
HPN
- ORD
1 stop12h 29m
Multiple Airlines
Wed 3/412:44 pm
ORD
- HPN
2 stops21h 44m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Mon 3/212:08 pm
HPN
- ORD
1 stop12h 29m
Multiple Airlines
Thu 3/511:55 am
ORD
- HPN
2 stops22h 33m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$361
This American Airlines deal was found by Cheapflights users on 2/15. 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 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 2/15![American Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 2/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/113:13 pm
HPN
- ORD
1 stop7h 13m
Delta
Tue 3/317:10 am
ORD
- HPN
1 stop3h 43m
Delta
Deal found 2/16![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 2/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/145:15 pm
HPN
- MDW
1 stop6h 16m
Delta
Sat 3/219:30 am
MDW
- HPN
1 stop6h 05m
Delta
Deal found 2/17![Delta logo]()
$405
This American Airlines deal was found by Cheapflights users on 2/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:37 pm
HPN
- ORD
Nonstop2h 48m
American Airlines
Tue 3/241:58 pm
ORD
- HPN
Nonstop2h 09m
American Airlines
Deal found 2/15![American Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 2/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
HPN
- MDW
1 stop7h 02m
Delta
Tue 3/246:00 am
MDW
- HPN
1 stop7h 29m
Delta
Deal found 2/15![Delta logo]()
$375
This Delta deal was found by Cheapflights users on 2/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/173:13 pm
HPN
- ORD
1 stop5h 36m
Delta
Tue 3/249:50 am
ORD
- HPN
1 stop7h 28m
Delta
Deal found 2/15![Delta logo]()
$375
This Delta deal was found by Cheapflights users on 2/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1812:35 pm
HPN
- MDW
1 stop6h 19m
Delta
Mon 3/239:30 am
MDW
- HPN
1 stop6h 07m
Delta
Deal found 2/16![Delta logo]()
$409
This American Airlines deal was found by Cheapflights users on 2/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2112:00 pm
HPN
- ORD
Nonstop2h 43m
American Airlines
Sun 3/296:38 pm
ORD
- HPN
Nonstop2h 21m
American Airlines
Deal found 2/16![American Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Mon 3/231:10 pm
HPN
- ORD
2 stops23h 40m
Multiple Airlines
Sun 3/2912:34 pm
ORD
- HPN
1 stop21h 54m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$333
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 17, 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 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:09 pm
HPN
- ORD
1 stop6h 07m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Mon 5/186:09 pm
HPN
- ORD
1 stop6h 07m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/912:08 pm
HPN
- ORD
2 stops30h 38m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:27 pm
HPN
- ORD
1 stop30h 16m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/108:00 am
HPN
- ORD
1 stop16h 16m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Mon 4/1312:08 pm
HPN
- ORD
2 stops32h 55m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:09 pm
HPN
- ORD
1 stop6h 07m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 3/41:27 pm
HPN
- MDW
2 stops25h 59m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 4/61:10 pm
HPN
- MDW
3 stops31h 57m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/612:08 pm
HPN
- MDW
2 stops26h 00m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 6/218:00 am
HPN
- MDW
3 stops36h 30m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Tue 3/3112:08 pm
HPN
- MDW
3 stops32h 59m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$270
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 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $262 (Kiwi.com) |
One-way from | $95 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $212 |
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 17, 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 5/15
6:09 pm-11:16 pm
1 stop6h 07m
Chicago O'Hare Intl
Mon 5/18
6:57 am-11:27 am
2 stops27h 30m
$284
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Sat 5/16
12:45 pm-9:09 pm
1 stop9h 24m
Chicago Midway
Tue 5/19
9:23 am-4:36 pm
1 stop6h 13m
$346
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Sat 5/16
12:00 pm-1:43 pm
Nonstop2h 43m
Chicago O'Hare Intl
Tue 5/19
6:36 pm-9:59 pm
Nonstop2h 23m
$355
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Fri 4/10
12:08 pm-5:16 pm
1 stop6h 08m
Chicago O'Hare Intl
Tue 4/14
5:01 am-12:47 pm
2 stops30h 46m
$368
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Wed 4/1
6:30 am-8:20 am
Nonstop2h 50m
Chicago O'Hare Intl
Wed 4/15
5:00 am-1:00 pm
1 stop7h 00m
$370
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Tue 3/17
6:00 am-12:02 pm
1 stop7h 02m
Chicago Midway
Tue 3/24
6:00 am-2:29 pm
1 stop7h 29m
$375
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Wed 4/1
12:35 pm-5:54 pm
1 stop6h 19m
Chicago Midway
Wed 4/15
6:00 am-12:00 pm
1 stop5h 00m
$375
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
Tue 7/21
12:45 pm-6:31 pm
1 stop6h 46m
Chicago Midway
Tue 7/28
9:30 am-4:33 pm
1 stop6h 03m
$375
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Sat 7/4
3:15 pm-9:34 pm
1 stop7h 19m
Chicago O'Hare Intl
Wed 7/8
7:10 am-11:44 am
1 stop3h 34m
$375
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
Wed 4/15
6:00 am-1:14 pm
1 stop8h 14m
Chicago O'Hare Intl
Sat 4/18
7:00 am-11:49 am
1 stop3h 49m
$375
Showing 1-10 of 38 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 $272). 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 17, 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.
Weekly flight availability from Westchester County to Chicago
Explore weekly flight availability from Westchester County to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 17, 2026.
The most flights from zzREU to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).
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 17, 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.
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Crew
8.5
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Westchester County to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 17, 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 17, 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$371 | Average$482 | FlexibilityNo cancel fee | On-time71% |