$125+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
May 17 — May 241
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
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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 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 April 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 April 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/148:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Sun 5/178:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 5/78:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Mon 5/116:09 pm
HPN
- ORD
2 stops26h 42m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$355
This American Airlines deal was found by Cheapflights users on 4/14. 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 8/158:18 am
ORD
- HPN
Nonstop2h 10m
American Airlines
Sat 8/226:00 am
HPN
- ORD
Nonstop2h 35m
American Airlines
Deal found 4/14![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 4/14. 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 6/237:17 pm
ORD
- HPN
1 stop15h 38m
Delta
Sat 7/45:10 pm
HPN
- ORD
1 stop4h 21m
Delta
Deal found 4/14![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 4/14. 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 6/139:17 am
MDW
- HPN
1 stop5h 32m
Delta
Mon 6/155:10 pm
HPN
- MDW
1 stop17h 04m
Delta
Deal found 4/14![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 4/14. 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 6/247:01 am
ORD
- HPN
2 stops14h 24m
Delta
Wed 7/15:10 pm
HPN
- ORD
1 stop4h 21m
Delta
Deal found 4/14![Delta logo]()
$404
This Delta deal was found by Cheapflights users on 4/16. 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 8/155:30 am
ORD
- HPN
1 stop8h 02m
Delta
Sat 8/2212:45 pm
HPN
- ORD
1 stop4h 51m
Delta
Deal found 4/16![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/13. 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.
Tue 5/269:22 am
MDW
- HPN
1 stop5h 27m
Delta
Sat 5/304:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Deal found 4/13![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/16. 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 5/269:25 am
ORD
- HPN
2 stops11h 55m
Delta
Sat 5/306:00 am
HPN
- ORD
1 stop8h 01m
Delta
Deal found 4/16![Delta logo]()
$424
This American Airlines deal was found by Cheapflights users on 4/14. 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 4/1812:32 pm
ORD
- HPN
Nonstop2h 16m
American Airlines
Sat 5/166:35 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
Deal found 4/14![American Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Sat 5/21:27 pm
ORD
- HPN
2 stops45h 01m
Multiple Airlines
Sat 5/912:00 pm
HPN
- ORD
1 stop27h 39m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 4/16. 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 5/269:22 am
MDW
- HPN
1 stop5h 27m
Delta
Fri 5/296:40 pm
HPN
- MDW
1 stop16h 19m
Delta
Deal found 4/16![Delta logo]()
$431
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 April 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 April 17, 2026.
This Delta deal was found by Cheapflights users on 4/13. 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 5/2711:09 am
ORD
- HPN
1 stop3h 40m
Delta
Sat 5/305:15 pm
HPN
- ORD
1 stop3h 59m
Delta
Deal found 4/13![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/13. 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.
Tue 5/2611:09 am
ORD
- HPN
1 stop3h 40m
Delta
Sat 5/306:40 pm
HPN
- ORD
1 stop6h 23m
Delta
Deal found 4/13![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/15. 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 6/166:05 am
MDW
- HPN
1 stop5h 04m
Delta
Wed 7/812:35 pm
HPN
- MDW
1 stop6h 50m
Delta
Deal found 4/15![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/16. 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 5/2710:59 am
MDW
- HPN
1 stop6h 01m
Delta
Fri 5/296:40 pm
HPN
- MDW
1 stop16h 19m
Delta
Deal found 4/16![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 4/16. 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 5/269:22 am
MDW
- HPN
1 stop5h 27m
Delta
Fri 5/296:40 pm
HPN
- MDW
1 stop16h 19m
Delta
Deal found 4/16![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 4/13. 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 5/2810:59 am
MDW
- HPN
1 stop6h 01m
Delta
Sat 5/304:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Deal found 4/13![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 4/13. 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.
Fri 5/2911:09 am
ORD
- HPN
1 stop3h 40m
Delta
Mon 6/16:40 pm
HPN
- ORD
1 stop6h 19m
Delta
Deal found 4/13![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/13. 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.
Tue 5/269:25 am
ORD
- HPN
1 stop5h 24m
Delta
Thu 6/412:31 pm
HPN
- ORD
1 stop6h 34m
Delta
Deal found 4/13![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/16. 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.
Thu 8/207:10 am
ORD
- HPN
1 stop3h 34m
Delta
Tue 8/255:10 pm
HPN
- ORD
1 stop4h 14m
Delta
Deal found 4/16![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/13. 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 5/308:10 am
ORD
- HPN
1 stop5h 19m
Delta
Sun 5/316:00 am
HPN
- ORD
1 stop5h 16m
Delta
Deal found 4/13![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/13. 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 5/305:30 am
ORD
- HPN
1 stop5h 32m
Delta
Mon 6/16:40 pm
HPN
- ORD
1 stop6h 19m
Delta
Deal found 4/13![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/15. 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 9/55:30 am
ORD
- HPN
1 stop5h 43m
Delta
Mon 9/74:19 pm
HPN
- ORD
1 stop8h 38m
Delta
Deal found 4/15![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/13. 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.
Tue 5/269:22 am
MDW
- HPN
1 stop5h 27m
Delta
Thu 6/412:31 pm
HPN
- MDW
1 stop7h 02m
Delta
Deal found 4/13![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/13. 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.
Mon 6/16:23 am
MDW
- HPN
1 stop7h 06m
Delta
Tue 6/96:29 am
HPN
- MDW
1 stop6h 31m
Delta
Deal found 4/13![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/14. 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 6/139:17 am
MDW
- HPN
1 stop5h 32m
Delta
Mon 6/155:10 pm
HPN
- MDW
1 stop17h 04m
Delta
Deal found 4/14![Delta logo]()
$450
This Delta deal was found by Cheapflights users on 4/13. 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.
Fri 5/299:22 am
MDW
- HPN
1 stop5h 27m
Delta
Sun 5/314:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Deal found 4/13![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 4/13. 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 5/309:22 am
MDW
- HPN
1 stop5h 27m
Delta
Sun 5/314:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Deal found 4/13![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 4/16. 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.
Fri 10/21:15 pm
ORD
- HPN
1 stop7h 27m
Delta
Sun 10/43:15 pm
HPN
- ORD
1 stop5h 28m
Delta
Deal found 4/16![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 4/12. 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 9/106:00 am
MDW
- HPN
1 stop5h 13m
Delta
Sun 9/136:00 am
HPN
- MDW
1 stop6h 54m
Delta
Deal found 4/12![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 4/15. 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 5/239:22 am
MDW
- HPN
1 stop5h 27m
Delta
Tue 5/264:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Deal found 4/15![Delta logo]()
$515
This Delta deal was found by Cheapflights users on 4/13. 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.
Fri 5/111:00 am
ORD
- HPN
1 stop3h 49m
Delta
Sun 5/312:48 pm
HPN
- ORD
1 stop7h 02m
Delta
Deal found 4/13![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 4/12. 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.
Fri 5/811:09 am
ORD
- HPN
1 stop3h 40m
Delta
Mon 5/114:29 pm
HPN
- ORD
1 stop6h 24m
Delta
Deal found 4/12![Delta logo]()
$543
Last-minute flights from Chicago to Westchester CountyDiscover last-minute flight deals from Chicago to Westchester County. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Westchester County. Data last updated April 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/14. 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 4/1812:32 pm
ORD
- HPN
Nonstop2h 16m
American Airlines
Sat 5/166:35 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
Deal found 4/14![American Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 4/16. 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 4/189:46 am
MDW
- HPN
1 stop5h 54m
Delta
Sat 5/164:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Deal found 4/16![Delta logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Sat 5/21:27 pm
ORD
- HPN
2 stops45h 01m
Multiple Airlines
Sat 5/912:00 pm
HPN
- ORD
1 stop27h 39m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 5/78:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Mon 5/116:09 pm
HPN
- ORD
2 stops26h 42m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$355
This American Airlines deal was found by Cheapflights users on 4/13. 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.
Wed 5/133:26 pm
ORD
- HPN
1 stop6h 34m
American Airlines
Wed 5/207:00 am
HPN
- ORD
Nonstop2h 49m
American Airlines
Deal found 4/13![American Airlines logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/148:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Sun 5/178:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 4/16. 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 5/166:36 pm
ORD
- HPN
Nonstop2h 23m
American Airlines
Sun 5/177:00 am
HPN
- ORD
Nonstop2h 49m
American Airlines
Deal found 4/16![American Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 4/13. 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.
Tue 5/2611:09 am
ORD
- HPN
1 stop3h 40m
Delta
Sat 5/306:40 pm
HPN
- ORD
1 stop6h 23m
Delta
Deal found 4/13![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/13. 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.
Tue 5/269:22 am
MDW
- HPN
1 stop5h 27m
Delta
Sat 5/304:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Deal found 4/13![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/16. 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 5/269:22 am
MDW
- HPN
1 stop5h 27m
Delta
Fri 5/296:40 pm
HPN
- MDW
1 stop16h 19m
Delta
Deal found 4/16![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 4/13. 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 5/279:22 am
MDW
- HPN
1 stop5h 27m
Delta
Fri 5/296:40 pm
HPN
- MDW
1 stop16h 19m
Delta
Deal found 4/13![Delta logo]()
$442
This American Airlines deal was found by Cheapflights users on 4/14. 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.
Fri 5/298:10 am
ORD
- HPN
Nonstop2h 19m
American Airlines
Sun 5/317:10 am
HPN
- ORD
Nonstop2h 43m
American Airlines
Deal found 4/14![American Airlines logo]()
$429
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 April 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 April 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 6/96:00 am
MDW
- HPN
2 stops28h 20m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 4/12. 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.
Thu 4/231:12 pm
ORD
- HPN
1 stop21h 16m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Wed 5/2712:04 pm
MDW
- HPN
2 stops31h 55m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 4/297:15 pm
ORD
- HPN
2 stops39h 13m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/1710:22 am
ORD
- HPN
2 stops30h 07m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/291:50 pm
ORD
- HPN
2 stops20h 30m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/131:59 pm
ORD
- HPN
2 stops30h 00m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/1312:04 pm
MDW
- HPN
2 stops31h 55m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/156:55 am
ORD
- HPN
2 stops27h 25m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 6/56:00 am
MDW
- HPN
2 stops28h 20m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 4/267:30 am
MDW
- HPN
2 stops50h 58m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$163
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 April 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $289 (Kiwi.com) |
One-way from | $125 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $231 |
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 April 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
Quickest round-trip
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Wed 5/27
11:09 am-3:49 pm
1 stop3h 40m
White Plains Westchester County
Sat 5/30
5:15 pm-8:14 pm
1 stop3h 59m
$415
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Tue 5/26
11:09 am-3:49 pm
1 stop3h 40m
White Plains Westchester County
Sat 5/30
6:40 pm-12:03 am
1 stop6h 23m
$415
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Tue 6/16
6:05 am-12:09 pm
1 stop5h 04m
White Plains Westchester County
Wed 7/8
12:35 pm-6:25 pm
1 stop6h 50m
$415
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Wed 5/27
10:59 am-6:00 pm
1 stop6h 01m
White Plains Westchester County
Fri 5/29
6:40 pm-9:59 am
1 stop16h 19m
$431
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Tue 5/26
9:22 am-3:49 pm
1 stop5h 27m
White Plains Westchester County
Fri 5/29
6:40 pm-9:59 am
1 stop16h 19m
$431
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Thu 5/28
10:59 am-6:00 pm
1 stop6h 01m
White Plains Westchester County
Sat 5/30
4:29 pm-9:09 pm
1 stop5h 40m
$447
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Fri 5/29
11:09 am-3:49 pm
1 stop3h 40m
White Plains Westchester County
Mon 6/1
6:40 pm-11:59 pm
1 stop6h 19m
$449
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Tue 5/26
9:25 am-3:49 pm
1 stop5h 24m
White Plains Westchester County
Thu 6/4
12:31 pm-6:05 pm
1 stop6h 34m
$449
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Thu 8/20
7:10 am-11:44 am
1 stop3h 34m
White Plains Westchester County
Tue 8/25
5:10 pm-8:24 pm
1 stop4h 14m
$449
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 5/30
8:10 am-2:29 pm
1 stop5h 19m
White Plains Westchester County
Sun 5/31
6:00 am-10:16 am
1 stop5h 16m
$449
Showing 1-10 of 45 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, March is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $124). Flying from Chicago to Westchester County in February is currently the most expensive (average of $415). 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 April 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 4% on airfare.
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 April 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 afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 17, 2026.
The most flights from CHI to zzREU are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).
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 April 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.
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.9
Overall
7.1
Food
6.4
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.9
Overall
7.1
Food
6.4
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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Alternative routes for Chicago to Westchester County
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Complete your trip
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Search flights from Chicago to Westchester County by cabin class
Find flights from Chicago to Westchester County, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Westchester County flights
Browse other Chicago and Westchester County flight options. Last updated on April 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 April 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$380 | Average$487 | FlexibilityNo cancel fee | On-time71% |