$146+ Cheap flights from Chicago (CHI) to Westchester County
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Oct 18 — Oct 251
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Westchester County with Cheapflights
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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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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 September 18, 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 September 18, 2026.
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/28:39 am -
1 stop6h 09m
Wed 12/912:59 pm -
1 stop7h 06m
Deal found 9/18![Delta logo]()
$381
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/72:02 pm -
Nonstop2h 14m
Sat 11/145:50 pm -
Nonstop2h 59m
Deal found 9/18![American Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 12/1611:28 am -
1 stop5h 32m
Wed 1/204:19 pm -
1 stop6h 51m
Deal found 9/17![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 10/145:27 am -
1 stop5h 41m
Wed 10/216:40 pm -
1 stop6h 17m
Deal found 9/17![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 9/15. 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 10/177:00 am -
1 stop3h 50m
Tue 10/206:40 pm -
1 stop6h 17m
Deal found 9/15![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 9/17. 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 10/179:29 am -
1 stop5h 19m
Sat 10/2412:30 pm -
1 stop6h 30m
Deal found 9/17![Delta logo]()
$421
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/1412:39 pm -
Nonstop2h 20m
Sat 10/174:30 pm -
Nonstop2h 52m
Deal found 9/15![American Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/177:29 pm -
Nonstop2h 26m
Sun 10/186:39 am -
1 stop4h 28m
Deal found 9/14![American Airlines logo]()
$446
This Delta deal was found by Cheapflights users on 9/15. 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 10/148:29 am -
1 stop6h 19m
Tue 10/206:40 pm -
1 stop6h 17m
Deal found 9/15![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 9/14. 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 10/136:04 am -
1 stop5h 04m
Tue 10/204:29 pm -
1 stop7h 04m
Deal found 9/14![Delta logo]()
$447
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 9/227:34 pm -
Nonstop2h 25m
Sat 9/265:36 pm -
Nonstop2h 54m
Deal found 9/16![American Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 9/15. 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 12/49:59 am -
1 stop5h 36m
Tue 12/1512:59 pm -
1 stop7h 06m
Deal found 9/15![Delta logo]()
$457
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 September 18, 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 September 18, 2026.
This Delta deal was found by Cheapflights users on 9/14. 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 9/237:05 am -
1 stop3h 51m
Wed 9/305:20 pm -
1 stop4h 10m
Deal found 9/14![Delta logo]()
$473
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/178:40 am -
1 stop5h 06m
Sun 10/186:39 am -
1 stop4h 28m
Deal found 9/13![American Airlines logo]()
$537
This United deal was found by Cheapflights users on 9/16. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:20 pm -
2 stops18h 39m
Sun 11/15:24 pm -
2 stops18h 51m
Deal found 9/16![Multiple Airlines logo]()
$719
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 10/88:29 am -
1 stop6h 19m
Tue 10/133:15 pm -
1 stop7h 12m
Deal found 9/15![Delta logo]()
$508
This Delta deal was found by Cheapflights users on 9/16. 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 10/109:29 am -
1 stop5h 19m
Mon 10/1212:30 pm -
1 stop6h 30m
Deal found 9/16![Delta logo]()
$508
This Delta deal was found by Cheapflights users on 9/15. 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 9/3010:48 am -
1 stop6h 12m
Sun 10/412:40 pm -
1 stop6h 53m
Deal found 9/15![Delta logo]()
$520
This KAYAK deal was found by Cheapflights users on 9/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:25 am -
1 stop7h 15m
Thu 10/15:20 pm -
1 stop4h 10m
Deal found 9/15![Delta logo]()
$540
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 9/247:05 am -
1 stop3h 51m
Thu 10/15:20 pm -
1 stop4h 10m
Deal found 9/14![Delta logo]()
$543
This KAYAK deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:48 am -
1 stop6h 12m
Wed 10/712:30 pm -
1 stop6h 30m
Deal found 9/18![Delta logo]()
$551
This Delta deal was found by Cheapflights users on 9/15. 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 9/288:25 am -
1 stop7h 15m
Tue 9/295:20 pm -
1 stop4h 10m
Deal found 9/15![Delta logo]()
$567
This Delta deal was found by Cheapflights users on 9/15. 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 9/289:59 am -
1 stop5h 41m
Tue 9/296:00 am -
1 stop6h 54m
Deal found 9/15![Delta logo]()
$567
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 9/306:05 am -
1 stop4h 58m
Mon 10/512:40 pm -
1 stop6h 53m
Deal found 9/17![Delta logo]()
$586
This Delta deal was found by Cheapflights users on 9/15. 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 9/296:05 am -
1 stop4h 58m
Mon 10/56:40 pm -
1 stop5h 04m
Deal found 9/15![Delta logo]()
$586
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 10/88:29 am -
1 stop6h 19m
Sun 10/1112:30 pm -
1 stop6h 59m
Deal found 9/15![Delta logo]()
$621
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 10/2911:19 am -
2 stops9h 58m
Tue 11/34:29 pm -
1 stop8h 28m
Deal found 9/14![Delta logo]()
$665
This Delta deal was found by Cheapflights users on 9/14. 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 10/136:04 am -
2 stops8h 44m
Tue 10/204:29 pm -
1 stop7h 04m
Deal found 9/14![Delta logo]()
$665
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 10/299:29 am -
2 stops11h 48m
Sun 11/112:30 pm -
1 stop6h 30m
Deal found 9/15![Delta logo]()
$701
This Delta deal was found by Cheapflights users on 9/16. 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 9/265:30 am -
1 stop5h 38m
Mon 9/2812:50 pm -
2 stops8h 40m
Deal found 9/16![Delta logo]()
$721
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/239:59 am -
2 stops11h 18m
Fri 11/64:29 pm -
1 stop8h 28m
Deal found 9/18![Delta logo]()
$721
This Delta deal was found by Cheapflights users on 9/13. 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 9/258:55 am -
1 stop5h 50m
Mon 9/2812:40 pm -
2 stops7h 53m
Deal found 9/13![Delta logo]()
$756
Last-minute flights from Chicago to Westchester CountyDiscover last-minute flight deals from Chicago to Westchester County. Data last updated September 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Westchester County. Data last updated September 18, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/17. 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.
Mon 9/216:05 am -
1 stop4h 58m
Wed 9/306:40 pm -
1 stop5h 04m
Deal found 9/17![Delta logo]()
$468
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 9/227:34 pm -
Nonstop2h 25m
Sat 9/265:36 pm -
Nonstop2h 54m
Deal found 9/16![American Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 9/14. 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 10/136:04 am -
1 stop5h 04m
Tue 10/204:29 pm -
1 stop7h 04m
Deal found 9/14![Delta logo]()
$447
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 10/1412:39 pm -
Nonstop2h 20m
Wed 10/214:30 pm -
Nonstop2h 52m
Deal found 9/14![American Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 10/145:27 am -
1 stop5h 41m
Wed 10/216:40 pm -
1 stop6h 17m
Deal found 9/17![Delta logo]()
$407
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/1412:39 pm -
Nonstop2h 20m
Sat 10/174:30 pm -
Nonstop2h 52m
Deal found 9/15![American Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 9/15. 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 10/148:29 am -
1 stop6h 19m
Tue 10/206:40 pm -
1 stop6h 17m
Deal found 9/15![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 10/158:29 am -
1 stop6h 19m
Wed 10/215:22 pm -
1 stop4h 08m
Deal found 9/15![Delta logo]()
$457
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/162:00 pm -
Nonstop2h 24m
Tue 10/205:54 pm -
Nonstop2h 52m
Deal found 9/18![American Airlines logo]()
$462
This Delta deal was found by Cheapflights users on 9/15. 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 10/177:00 am -
1 stop3h 50m
Tue 10/206:40 pm -
1 stop6h 17m
Deal found 9/15![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 9/17. 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 10/179:29 am -
1 stop5h 19m
Sat 10/2412:30 pm -
1 stop6h 30m
Deal found 9/17![Delta logo]()
$421
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/177:29 pm -
Nonstop2h 26m
Sun 10/186:39 am -
1 stop4h 28m
Deal found 9/14![American Airlines logo]()
$446
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 September 18, 2026.
Search for one-way flight options from Chicago to Westchester County. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/289:51 am -
2 stops10h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Tue 10/277:15 am -
2 stops12h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/268:36 am -
2 stops25h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Tue 11/177:15 am -
2 stops12h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/155:35 am -
2 stops38h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/94:42 pm -
2 stops27h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/187:15 am -
2 stops12h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/279:53 am -
3 stops34h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/149:34 pm -
2 stops22h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/96:16 am -
2 stops37h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/76:25 am -
2 stops13h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$199
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 September 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $381 (Delta) |
One-way from | $146 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $295 |
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 7,457,451 searches. Data last updated September 18, 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 Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Thu 11/12
5:30 am-2:29 pm
1 stop7h 59m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$284
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Tue 10/6
1:23 pm-10:17 pm
1 stop7h 54m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$284
Quickest round-trip
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Thu 11/26
7:05 am-11:49 am
1 stop3h 44m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$284
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Thu 10/22
5:27 am-12:08 pm
1 stop5h 41m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$284
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Thu 10/1
6:05 am-12:03 pm
1 stop4h 58m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$284
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Wed 11/25
1:05 pm-10:09 pm
1 stop8h 04m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$284
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Wed 10/21
6:04 am-12:08 pm
1 stop5h 04m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$284
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Wed 12/16
6:20 am-4:35 pm
1 stop9h 15m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$352
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Thu 12/17
11:35 am-10:11 pm
1 stop9h 36m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$387
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Thu 10/1
5:20 am-1:12 pm
1 stop6h 52m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$391
Showing 1-10 of 40 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 $530). 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 September 18, 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 8% 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 September 18, 2026.
The most flights from CHI to zzREU are scheduled on a Thursday (10 on average). You will have fewer flight options on Monday, 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 September 12, 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 September 18, 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.
Entertainment
6.8
Boarding
7.4
Overall
7.1
Comfort
7.2
Food
6.4
Crew
7.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Entertainment
6.8
Boarding
7.4
Overall
7.1
Comfort
7.2
Food
6.4
Crew
7.9
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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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 September 18, 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 7,457,451 searches. Data last updated September 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$380 | Average$490 | FlexibilityNo cancel fee | On-time71% |