$135+ Cheap flights from Chicago (CHI) to Westchester County
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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Aug 16 — Aug 231
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Westchester County 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 Chicago to Westchester County
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Cheapest flights from Chicago to Westchester CountyExplore the most affordable flight options available from Chicago to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 17, 2026.
Explore the most affordable flight options available from Chicago to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 17, 2026.
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Sat 7/257:37 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Tue 7/284:39 pm
HPN
- ORD
Nonstop2h 50m
American Airlines
Deal found 7/15![American Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 7/16. 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 7/285:30 am
ORD
- HPN
1 stop5h 38m
Delta
Sat 8/15:12 pm
HPN
- ORD
1 stop4h 19m
Delta
Deal found 7/16![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 7/16. 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 7/286:00 am
MDW
- HPN
1 stop7h 29m
Delta
Sat 8/14:29 pm
HPN
- MDW
1 stop6h 46m
Delta
Deal found 7/16![Delta logo]()
$371
This American Airlines deal was found by Cheapflights users on 7/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:29 pm
ORD
- HPN
Nonstop2h 17m
American Airlines
Sun 9/612:08 pm
HPN
- ORD
Nonstop2h 36m
American Airlines
Deal found 7/17![American Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Sat 7/187:37 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Mon 7/205:45 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
Deal found 7/15![American Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 7/16. 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 7/182:05 pm
ORD
- HPN
Nonstop2h 20m
American Airlines
Sun 7/197:10 am
HPN
- ORD
Nonstop2h 41m
American Airlines
Deal found 7/16![American Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 7/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:11 am
ORD
- HPN
Nonstop2h 18m
American Airlines
Tue 8/185:45 pm
HPN
- ORD
Nonstop2h 53m
American Airlines
Deal found 7/13![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 7/15. 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.
Sat 7/185:30 am
ORD
- HPN
1 stop5h 38m
Delta
Mon 7/275:12 pm
HPN
- ORD
1 stop4h 19m
Delta
Deal found 7/15![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 7/15. 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 9/189:29 am
MDW
- HPN
1 stop5h 16m
Delta
Tue 9/226:00 am
HPN
- MDW
1 stop6h 55m
Delta
Deal found 7/15![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 7/16. 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.
Sat 9/129:59 am
MDW
- HPN
1 stop5h 41m
Delta
Mon 9/145:20 pm
HPN
- MDW
1 stop16h 47m
Delta
Deal found 7/16![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 7/12. 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.
Sat 8/153:25 pm
ORD
- HPN
1 stop5h 56m
Delta
Sat 8/223:10 pm
HPN
- ORD
1 stop7h 37m
Delta
Deal found 7/12![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 7/12. 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.
Tue 8/1110:54 am
MDW
- HPN
1 stop6h 13m
Delta
Tue 8/186:00 am
HPN
- MDW
1 stop6h 51m
Delta
Deal found 7/12![Delta logo]()
$415
Best flights from Chicago to Westchester CountyDiscover carefully curated flight deals from Chicago to Westchester County that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 17, 2026.
Discover carefully curated flight deals from Chicago to Westchester County that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 17, 2026.
This Delta deal was found by Cheapflights users on 7/15. 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.
Sat 7/255:30 am
ORD
- HPN
1 stop7h 59m
Delta
Wed 9/3012:40 pm
HPN
- ORD
1 stop4h 34m
Delta
Deal found 7/15![Delta logo]()
$371
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Tue 8/117:38 pm
ORD
- HPN
Nonstop2h 21m
American Airlines
Tue 8/186:00 am
HPN
- ORD
Nonstop2h 40m
American Airlines
Deal found 7/12![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 7/16. 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 12/89:55 am
MDW
- HPN
1 stop5h 46m
Delta
Sat 12/1212:45 pm
HPN
- MDW
1 stop6h 52m
Delta
Deal found 7/16![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 7/16. 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 7/286:00 am
MDW
- HPN
1 stop7h 29m
Delta
Wed 8/54:29 pm
HPN
- MDW
1 stop7h 07m
Delta
Deal found 7/16![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 7/16. 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 7/286:00 am
MDW
- HPN
1 stop7h 29m
Delta
Sat 8/14:29 pm
HPN
- MDW
1 stop6h 46m
Delta
Deal found 7/16![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 7/16. 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 12/96:00 am
MDW
- HPN
1 stop5h 11m
Delta
Sat 12/124:19 pm
HPN
- MDW
1 stop6h 51m
Delta
Deal found 7/16![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 7/14. 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 9/41:50 pm
ORD
- HPN
1 stop7h 31m
Delta
Tue 9/86:40 pm
HPN
- ORD
1 stop6h 19m
Delta
Deal found 7/14![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 7/14. 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 8/146:05 am
MDW
- HPN
1 stop4h 58m
Delta
Sat 8/1512:36 pm
HPN
- MDW
1 stop6h 57m
Delta
Deal found 7/14![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 7/15. 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.
Mon 9/146:05 am
MDW
- HPN
1 stop4h 58m
Delta
Sat 9/196:40 pm
HPN
- MDW
1 stop5h 05m
Delta
Deal found 7/15![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 7/16. 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.
Sat 9/129:59 am
MDW
- HPN
1 stop5h 41m
Delta
Mon 9/145:20 pm
HPN
- MDW
1 stop16h 47m
Delta
Deal found 7/16![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 7/12. 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.
Tue 8/1110:54 am
MDW
- HPN
1 stop6h 13m
Delta
Tue 8/186:00 am
HPN
- MDW
1 stop6h 51m
Delta
Deal found 7/12![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 7/15. 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 9/2510:48 am
MDW
- HPN
1 stop6h 12m
Delta
Sun 9/276:00 am
HPN
- MDW
1 stop6h 55m
Delta
Deal found 7/15![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 7/14. 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.
Tue 8/119:24 am
MDW
- HPN
1 stop5h 24m
Delta
Sat 8/1512:36 pm
HPN
- MDW
1 stop6h 57m
Delta
Deal found 7/14![Delta logo]()
$445
This Delta deal was found by Cheapflights users on 7/14. 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.
Tue 8/256:05 am
MDW
- HPN
1 stop4h 58m
Delta
Mon 8/3110:29 am
HPN
- MDW
1 stop6h 15m
Delta
Deal found 7/14![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 7/16. 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.
Sat 12/126:00 am
MDW
- HPN
1 stop5h 11m
Delta
Sat 12/125:10 pm
HPN
- MDW
1 stop16h 35m
Delta
Deal found 7/16![Delta logo]()
$461
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/291:44 pm
ORD
- HPN
1 stop7h 41m
Delta
Tue 8/412:48 pm
HPN
- ORD
1 stop7h 01m
Delta
Deal found 7/13![Delta logo]()
$475
This Delta deal was found by Cheapflights users on 7/14. 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 8/283:25 pm
ORD
- HPN
1 stop5h 56m
Delta
Fri 9/44:29 pm
HPN
- ORD
1 stop8h 28m
Delta
Deal found 7/14![Delta logo]()
$503
This Delta deal was found by Cheapflights users on 7/15. 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.
Sat 7/256:30 am
ORD
- HPN
2 stops8h 17m
Delta
Tue 7/2812:36 pm
HPN
- ORD
1 stop4h 47m
Delta
Deal found 7/15![Delta logo]()
$590
This Delta deal was found by Cheapflights users on 7/12. 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.
Tue 8/1110:33 am
ORD
- HPN
1 stop6h 34m
Delta
Tue 8/186:00 am
HPN
- ORD
2 stops8h 08m
Delta
Deal found 7/12![Delta logo]()
$592
This Delta deal was found by Cheapflights users on 7/17. 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.
Tue 9/86:40 am
ORD
- HPN
1 stop6h 49m
Delta
Thu 10/156:00 am
HPN
- ORD
2 stops11h 40m
Delta
Deal found 7/17![Delta logo]()
$620
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:59 am
ORD
- HPN
1 stop3h 57m
Delta
Thu 9/310:29 am
HPN
- ORD
2 stops9h 00m
Delta
Deal found 7/13![Delta logo]()
$636
Last-minute flights from Chicago to Westchester CountyDiscover last-minute flight deals from Chicago to Westchester County. Data last updated July 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Westchester County. Data last updated July 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Fri 7/176:29 pm
ORD
- HPN
Nonstop2h 28m
American Airlines
Sun 7/195:34 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
Deal found 7/15![American Airlines logo]()
$423
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Sat 7/187:37 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Mon 7/205:45 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
Deal found 7/15![American Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 7/16. 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 7/182:05 pm
ORD
- HPN
Nonstop2h 20m
American Airlines
Sun 7/197:10 am
HPN
- ORD
Nonstop2h 41m
American Airlines
Deal found 7/16![American Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 7/15. 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.
Sat 7/183:35 pm
ORD
- HPN
1 stop5h 50m
Delta
Sun 7/265:12 pm
HPN
- ORD
1 stop4h 19m
Delta
Deal found 7/15![Delta logo]()
$407
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Sat 7/257:37 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Tue 7/284:39 pm
HPN
- ORD
Nonstop2h 50m
American Airlines
Deal found 7/15![American Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 7/15. 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.
Sat 7/259:19 am
MDW
- HPN
1 stop5h 28m
Delta
Sun 9/206:40 pm
HPN
- MDW
1 stop5h 05m
Delta
Deal found 7/15![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 7/16. 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 7/288:03 am
ORD
- HPN
1 stop5h 26m
Delta
Tue 8/46:49 pm
HPN
- ORD
1 stop6h 08m
Delta
Deal found 7/16![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 7/16. 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 7/286:00 am
MDW
- HPN
1 stop7h 29m
Delta
Wed 8/54:29 pm
HPN
- MDW
1 stop7h 07m
Delta
Deal found 7/16![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 7/12. 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.
Tue 8/1110:54 am
MDW
- HPN
1 stop6h 13m
Delta
Tue 8/186:00 am
HPN
- MDW
1 stop6h 51m
Delta
Deal found 7/12![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 7/14. 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.
Tue 8/119:24 am
MDW
- HPN
1 stop5h 24m
Delta
Sat 8/1512:36 pm
HPN
- MDW
1 stop6h 57m
Delta
Deal found 7/14![Delta logo]()
$445
This American Airlines deal was found by Cheapflights users on 7/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:11 am
ORD
- HPN
Nonstop2h 18m
American Airlines
Tue 8/185:45 pm
HPN
- ORD
Nonstop2h 53m
American Airlines
Deal found 7/13![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/153:25 pm
ORD
- HPN
1 stop5h 56m
Delta
Tue 8/1812:36 pm
HPN
- ORD
1 stop4h 41m
Delta
Deal found 7/13![Delta logo]()
$415
One-way flights from Chicago to Westchester CountySearch for one-way flight options from Chicago to Westchester County. Find affordable one-way fares based on user searches. Data last updated July 17, 2026.
Search for one-way flight options from Chicago to Westchester County. Find affordable one-way fares based on user searches. Data last updated July 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:33 pm
ORD
- HPN
2 stops22h 27m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Tue 10/136:05 am
ORD
- HPN
2 stops13h 55m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:30 am
ORD
- HPN
2 stops37h 30m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:30 am
ORD
- HPN
2 stops13h 30m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Tue 8/188:05 am
ORD
- HPN
2 stops26h 15m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 7/16. 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.
Wed 9/234:49 pm
ORD
- HPN
2 stops27h 11m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 7/16. 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.
Thu 9/179:26 am
ORD
- HPN
2 stops10h 34m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/167:05 am
ORD
- HPN
2 stops33h 24m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 7/16. 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.
Thu 9/107:45 am
ORD
- HPN
2 stops26h 35m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/164:49 pm
ORD
- HPN
2 stops27h 11m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:05 am
MDW
- HPN
2 stops37h 55m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 7/16. 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.
Wed 9/2312:03 pm
MDW
- HPN
2 stops31h 57m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$177
Find flight deals from Chicago to Westchester County
Keep the following information in mind while searching for Chicago to Westchester County flight deals. Data was last updated July 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $351 (American Airlines) |
One-way from | $135 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $259 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Westchester County 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 July 17, 2026.
Use the filters below to find and compare flights from Chicago to Westchester County that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 7/25
5:30 am-2:29 pm
1 stop7h 59m
White Plains Westchester County
Wed 9/30
12:40 pm-4:14 pm
1 stop4h 34m
$371
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Tue 12/8
9:55 am-4:41 pm
1 stop5h 46m
White Plains Westchester County
Sat 12/12
12:45 pm-6:37 pm
1 stop6h 52m
$371
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Tue 7/28
6:00 am-2:29 pm
1 stop7h 29m
White Plains Westchester County
Wed 8/5
4:29 pm-10:36 pm
1 stop7h 07m
$371
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Tue 7/28
6:00 am-2:29 pm
1 stop7h 29m
White Plains Westchester County
Sat 8/1
4:29 pm-10:15 pm
1 stop6h 46m
$371
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Wed 12/9
6:00 am-12:11 pm
1 stop5h 11m
White Plains Westchester County
Sat 12/12
4:19 pm-10:10 pm
1 stop6h 51m
$371
Quickest round-trip
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Tue 8/11
7:38 pm-10:59 pm
Nonstop2h 21m
White Plains Westchester County
Tue 8/18
6:00 am-7:40 am
Nonstop2h 40m
$395
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Fri 9/4
1:50 pm-10:21 pm
1 stop7h 31m
White Plains Westchester County
Tue 9/8
6:40 pm-11:59 pm
1 stop6h 19m
$407
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Fri 8/14
6:05 am-12:03 pm
1 stop4h 58m
White Plains Westchester County
Sat 8/15
12:36 pm-6:33 pm
1 stop6h 57m
$407
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Mon 9/14
6:05 am-12:03 pm
1 stop4h 58m
White Plains Westchester County
Sat 9/19
6:40 pm-10:45 pm
1 stop5h 05m
$407
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Sat 9/12
9:59 am-4:40 pm
1 stop5h 41m
White Plains Westchester County
Mon 9/14
5:20 pm-9:07 am
1 stop16h 47m
$414
Showing 1-10 of 41 resultsSorted by cheapest first
Best time to book a flight from Chicago to Westchester County
Have a flexible travel schedule? Discover the best time to fly to Westchester County from Chicago with our price prediction graph.
ORD-HPN
MDW-HPN
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 Chicago to Westchester County
CHI-zzREU
ORD-HPN
MDW-HPN
What is the cheapest month to book a flight from Chicago to Westchester County?
Currently, January is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $399). Flying from Chicago to Westchester County in May is currently the most expensive (average of $523). 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 CHI to REU?
Find hourly flight availability from Chicago to Westchester County. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 17, 2026.
One of the essential ways to save on airfare from Chicago to Westchester County is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 5% on airfare.
Weekly flight availability from Chicago to Westchester County
Explore weekly flight availability from Chicago to Westchester County. 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 July 17, 2026.
The most flights from CHI to zzREU are scheduled on a Monday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).
What is the cheapest day to fly from Chicago to Westchester County?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Westchester County. Price data was last updated on July 11, 2026.
Travelers seeking maximum savings on their Chicago to Westchester County flight should consider departing on Saturday afternoons when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Westchester County
Get insights into the airlines that provide service to Westchester County. 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 Westchester County. Reviews last updated July 17, 2026.
Peruse reviews from past customers who have flown with American Airlines from Chicago to Westchester County to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.2
Crew
7.9
Boarding
7.5
Overall
7.1
Food
6.4
Entertainment
6.8
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Comfort
7.2
Crew
7.9
Boarding
7.5
Overall
7.1
Food
6.4
Entertainment
6.8
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Westchester County. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Chicago and Westchester County flights
Browse other Chicago and Westchester County flight options. Last updated on July 17, 2026.
Popular flight searches
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Top airline flying from Chicago to Westchester County
Discover the top airline that operate flights from Chicago to Westchester County. 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 July 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$380 | Average$493 | FlexibilityNo cancel fee | On-time71% |