$149+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Sep 30 — Oct 71
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 August 31, 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 August 31, 2026.
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/138:09 am -
Nonstop2h 20m
Wed 10/215:54 pm -
Nonstop2h 52m
Deal found 8/28![American Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/139:59 am -
1 stop5h 43m
Wed 10/214:29 pm -
1 stop8h 28m
Deal found 8/28![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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
Wed 10/214:29 pm -
1 stop7h 04m
Deal found 8/28![Delta logo]()
$401
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/261:44 pm -
Nonstop2h 21m
Sat 10/35:36 pm -
Nonstop2h 54m
Deal found 8/28![American Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/31:44 pm -
Nonstop2h 21m
Sun 10/47:06 am -
Nonstop2h 44m
Deal found 8/30![American Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/301:44 pm -
Nonstop2h 21m
Sun 10/46:00 am -
Nonstop2h 44m
Deal found 8/26![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 8/296:35 pm -
Nonstop2h 24m
Tue 9/17:12 am -
Nonstop2h 40m
Deal found 8/27![American Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/16:05 am -
1 stop4h 58m
Sat 10/1012:30 pm -
1 stop6h 30m
Deal found 8/26![Delta logo]()
$437
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/208:05 am -
Nonstop2h 24m
Tue 9/295:36 pm -
Nonstop2h 54m
Deal found 8/28![American Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/86:05 am -
1 stop7h 24m
Sat 9/1212:40 pm -
1 stop5h 17m
Deal found 8/30![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/76:04 am -
1 stop5h 04m
Tue 10/1312:30 pm -
1 stop6h 30m
Deal found 8/26![Delta logo]()
$470
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 -
1 stop5h 19m
Sun 11/112:30 pm -
1 stop6h 30m
Deal found 8/28![Delta logo]()
$473
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 August 31, 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 August 31, 2026.
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/105:27 am -
1 stop8h 02m
Tue 10/136:40 pm -
1 stop6h 17m
Deal found 8/29![Delta logo]()
$401
This United deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Thu 12/39:10 am -
2 stops22h 45m
Mon 12/79:26 am -
2 stops14h 03m
Deal found 8/27![Multiple Airlines logo]()
$598
This JetBlue deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/62:35 pm -
1 stop6h 55m
Tue 2/91:00 pm -
1 stop11h 44m
Deal found 8/30![JetBlue logo]()
$633
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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
Wed 10/214:29 pm -
1 stop7h 04m
Deal found 8/30![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/296:40 am -
1 stop6h 49m
Mon 10/56:40 pm -
1 stop6h 19m
Deal found 8/26![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/288:05 am -
1 stop5h 24m
Mon 11/26:40 pm -
1 stop6h 17m
Deal found 8/27![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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
Tue 10/206:40 pm -
1 stop6h 17m
Deal found 8/28![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 12/46:00 am -
1 stop5h 14m
Sun 12/66:00 am -
1 stop5h 29m
Deal found 8/30![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/78:05 am -
1 stop5h 24m
Sun 10/115:22 pm -
1 stop4h 08m
Deal found 8/26![Delta logo]()
$540
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/203:40 pm -
1 stop5h 37m
Fri 10/236:40 pm -
2 stops15h 13m
Deal found 8/30![Delta logo]()
$553
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 11/55:27 am -
1 stop5h 41m
Sun 11/156:00 am -
1 stop5h 25m
Deal found 8/30![Delta logo]()
$563
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/229:29 am -
1 stop5h 19m
Sat 10/2412:30 pm -
1 stop6h 30m
Deal found 8/30![Delta logo]()
$650
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/39:29 am -
1 stop5h 16m
Sun 10/412:40 pm -
1 stop6h 53m
Deal found 8/30![Delta logo]()
$650
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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.
Sun 10/185:27 am -
1 stop5h 41m
Fri 10/236:40 pm -
2 stops23h 01m
Deal found 8/30![Delta logo]()
$652
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/139:59 am -
1 stop5h 43m
Wed 10/216:00 am -
2 stops7h 59m
Deal found 8/30![Delta logo]()
$655
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/104:19 pm -
1 stop4h 58m
Tue 10/1312:30 pm -
2 stops11h 03m
Deal found 8/29![Delta logo]()
$655
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/61:27 pm -
2 stops7h 50m
Sun 10/116:00 am -
1 stop5h 03m
Deal found 8/26![Delta logo]()
$671
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/296:04 am -
2 stops8h 44m
Sun 11/112:30 pm -
1 stop6h 30m
Deal found 8/30![Delta logo]()
$691
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/89:29 am -
1 stop5h 19m
Tue 10/1312:30 pm -
2 stops11h 03m
Deal found 8/26![Delta logo]()
$694
Last-minute flights from Chicago to Westchester CountyDiscover last-minute flight deals from Chicago to Westchester County. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Westchester County. Data last updated August 31, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 8/296:35 pm -
Nonstop2h 24m
Tue 9/17:12 am -
Nonstop2h 40m
Deal found 8/27![American Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 8/291:50 pm -
1 stop7h 31m
Tue 9/84:25 pm -
1 stop8h 34m
Deal found 8/26![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/29:24 am -
1 stop5h 24m
Mon 9/76:00 am -
1 stop4h 59m
Deal found 8/30![Delta logo]()
$578
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/46:05 am -
1 stop4h 58m
Sat 9/54:29 pm -
1 stop7h 07m
Deal found 8/27![Delta logo]()
$488
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/49:24 am -
1 stop5h 24m
Mon 9/76:00 am -
1 stop4h 59m
Deal found 8/27![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/86:05 am -
1 stop7h 24m
Sat 9/1212:40 pm -
1 stop5h 17m
Deal found 8/30![Delta logo]()
$453
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/208:05 am -
Nonstop2h 24m
Tue 9/295:36 pm -
Nonstop2h 54m
Deal found 8/28![American Airlines logo]()
$442
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/261:44 pm -
Nonstop2h 21m
Sat 10/37:06 am -
Nonstop2h 44m
Deal found 8/27![American Airlines logo]()
$381
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/266:40 am -
1 stop6h 49m
Sat 10/312:40 pm -
1 stop4h 34m
Deal found 8/27![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/286:05 am -
1 stop4h 58m
Mon 10/56:40 pm -
1 stop5h 04m
Deal found 8/29![Delta logo]()
$536
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 stop7h 24m
Mon 10/56:40 pm -
1 stop5h 04m
Deal found 8/29![Delta logo]()
$500
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/301:44 pm -
Nonstop2h 21m
Sun 10/46:00 am -
Nonstop2h 44m
Deal found 8/26![American Airlines logo]()
$417
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 August 31, 2026.
Search for one-way flight options from Chicago to Westchester County. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/233:50 pm -
2 stops28h 10m
Deal found 8/26![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/268:11 pm -
2 stops14h 16m
Deal found 8/27![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/283:50 pm -
2 stops18h 37m
Deal found 8/26![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/173:50 pm -
2 stops18h 30m
Deal found 8/28![Multiple Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/279:51 am -
2 stops10h 09m
Deal found 8/27![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/297:50 am -
2 stops26h 30m
Deal found 8/27![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/297:11 am -
3 stops36h 49m
Deal found 8/26![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/286:46 pm -
2 stops25h 14m
Deal found 8/26![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/166:25 am -
2 stops13h 35m
Deal found 8/26![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/266:25 am -
2 stops13h 35m
Deal found 8/27![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/36:25 am -
2 stops13h 35m
Deal found 8/30![Multiple Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/276:42 pm -
3 stops25h 18m
Deal found 8/27![Multiple Airlines logo]()
$206
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 August 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $381 (American Airlines) |
One-way from | $149 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $271 |
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 August 31, 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
Sat 10/10
5:27 am-2:29 pm
1 stop8h 02m
White Plains Westchester County
Tue 10/13
6:40 pm-11:57 pm
1 stop6h 17m
$401
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Tue 10/13
6:04 am-12:08 pm
1 stop5h 04m
White Plains Westchester County
Wed 10/21
4:29 pm-10:33 pm
1 stop7h 04m
$401
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Tue 9/29
6:40 am-2:29 pm
1 stop6h 49m
White Plains Westchester County
Mon 10/5
6:40 pm-11:59 pm
1 stop6h 19m
$437
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Wed 10/28
8:05 am-2:29 pm
1 stop5h 24m
White Plains Westchester County
Mon 11/2
6:40 pm-11:57 pm
1 stop6h 17m
$437
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Thu 10/15
8:29 am-3:48 pm
1 stop6h 19m
White Plains Westchester County
Tue 10/20
6:40 pm-11:57 pm
1 stop6h 17m
$437
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Fri 12/4
6:00 am-12:14 pm
1 stop5h 14m
White Plains Westchester County
Sun 12/6
6:00 am-10:29 am
1 stop5h 29m
$473
Quickest round-trip
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Wed 10/7
8:05 am-2:29 pm
1 stop5h 24m
White Plains Westchester County
Sun 10/11
5:22 pm-8:30 pm
1 stop4h 08m
$540
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Tue 10/20
3:40 pm-10:17 pm
1 stop5h 37m
White Plains Westchester County
Fri 10/23
6:40 pm-8:53 am
2 stops15h 13m
$553
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Thu 11/5
5:27 am-12:08 pm
1 stop5h 41m
White Plains Westchester County
Sun 11/15
6:00 am-10:25 am
1 stop5h 25m
$563
ChicagoWhite Plains
ORD Chicago O'Hare Intl - HPN White Plains Westchester County
ORDHPN
Chicago O'Hare Intl
Thu 12/3
9:10 am-8:55 am
2 stops22h 45m
White Plains Westchester County
Mon 12/7
9:26 am-10:29 pm
2 stops14h 03m
$598
Showing 1-10 of 42 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.
MDW-HPN
ORD-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
MDW-HPN
ORD-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 August 31, 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 at noon tend to be the most expensive. A flight in the morning could potentially save you up to 9% 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 August 31, 2026.
The most flights from CHI to zzREU are scheduled on a Monday (10 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (6 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 August 29, 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 August 31, 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.
Overall
7.1
Food
6.4
Crew
7.9
Entertainment
6.8
Boarding
7.5
Comfort
7.2
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Overall
7.1
Food
6.4
Crew
7.9
Entertainment
6.8
Boarding
7.5
Comfort
7.2
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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Chicago and Westchester County flights
Browse other Chicago and Westchester County flight options. Last updated on August 31, 2026.
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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 August 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$380 | Average$490 | FlexibilityNo cancel fee | On-time71% |