$139+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Jul 3 — Jul 101
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 June 3, 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 June 3, 2026.
This American Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 8/156:35 pm
ORD
- HPN
Nonstop2h 24m
American Airlines
Sat 8/227:12 am
HPN
- ORD
Nonstop2h 40m
American Airlines
Deal found 6/1![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:17 pm
ORD
- HPN
1 stop15h 39m
Delta
Sat 7/256:49 pm
HPN
- ORD
1 stop6h 04m
Delta
Deal found 5/31![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:58 pm
MDW
- HPN
1 stop15h 58m
Delta
Sat 7/2512:36 pm
HPN
- MDW
1 stop6h 31m
Delta
Deal found 5/31![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 8/156:51 am
ORD
- HPN
1 stop4h 05m
Delta
Sat 8/2212:36 pm
HPN
- ORD
1 stop4h 41m
Delta
Deal found 6/1![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/56:05 am
MDW
- HPN
1 stop4h 58m
Delta
Sat 8/812:36 pm
HPN
- MDW
1 stop6h 57m
Delta
Deal found 5/31![Delta logo]()
$415
This American Airlines deal was found by Cheapflights users on 5/30. 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 6/137:29 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Sat 7/114:30 pm
HPN
- ORD
Nonstop2h 50m
American Airlines
Deal found 5/30![American Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 8/126:35 pm
ORD
- HPN
Nonstop2h 24m
American Airlines
Thu 8/204:30 pm
HPN
- ORD
Nonstop2h 49m
American Airlines
Deal found 6/1![American Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/277:01 am
ORD
- HPN
1 stop3h 57m
Delta
Mon 6/295:10 pm
HPN
- ORD
1 stop20h 54m
Delta
Deal found 6/1![Delta logo]()
$444
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 6/107:37 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Sat 6/135:59 pm
HPN
- ORD
Nonstop2h 54m
American Airlines
Deal found 6/2![American Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:17 pm
ORD
- HPN
1 stop15h 39m
Delta
Sun 7/266:00 am
HPN
- ORD
1 stop5h 10m
Delta
Deal found 5/31![Delta logo]()
$458
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/129:55 am
MDW
- HPN
1 stop5h 46m
Delta
Sun 12/1312:45 pm
HPN
- MDW
1 stop6h 52m
Delta
Deal found 6/1![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 6/106:00 am
MDW
- HPN
1 stop5h 09m
Delta
Sat 6/1312:38 pm
HPN
- MDW
1 stop6h 33m
Delta
Deal found 6/2![Delta logo]()
$475
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 June 3, 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 June 3, 2026.
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
MDW
- HPN
1 stop5h 14m
Delta
Wed 7/810:29 am
HPN
- MDW
1 stop6h 46m
Delta
Deal found 6/3![Delta logo]()
$415
This KAYAK deal was found by Cheapflights users on 5/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/145:59 pm
ORD
- HPN
1 stop4h 27m
American Airlines
Wed 6/176:59 pm
HPN
- ORD
1 stop5h 59m
American Airlines
Deal found 5/29![American Airlines logo]()
$714
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:05 am
ORD
- HPN
1 stop7h 42m
Delta
Thu 7/306:49 pm
HPN
- ORD
1 stop6h 04m
Delta
Deal found 6/2![Delta logo]()
$458
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/213:22 pm
ORD
- HPN
1 stop6h 03m
Delta
Thu 7/306:49 pm
HPN
- ORD
1 stop6h 04m
Delta
Deal found 6/2![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:19 am
MDW
- HPN
1 stop5h 28m
Delta
Mon 7/134:29 pm
HPN
- MDW
1 stop6h 46m
Delta
Deal found 6/3![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 5/30. 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 8/139:24 am
MDW
- HPN
1 stop5h 24m
Delta
Sun 8/166:00 am
HPN
- MDW
1 stop4h 59m
Delta
Deal found 5/30![Delta logo]()
$503
This KAYAK deal was found by Cheapflights users on 5/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/227:37 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Thu 6/257:24 am
HPN
- ORD
Nonstop2h 41m
American Airlines
Deal found 5/29![American Airlines logo]()
$729
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/29:17 am
MDW
- HPN
1 stop5h 32m
Delta
Thu 7/910:29 am
HPN
- MDW
1 stop6h 46m
Delta
Deal found 6/2![Delta logo]()
$503
This KAYAK deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 6/1412:42 pm
ORD
- HPN
Nonstop2h 17m
American Airlines
Thu 6/186:19 am
HPN
- ORD
Nonstop2h 41m
American Airlines
Deal found 6/2![American Airlines logo]()
$729
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/65:30 am
ORD
- HPN
1 stop5h 32m
Delta
Sun 6/712:38 pm
HPN
- ORD
1 stop6h 51m
Delta
Deal found 6/3![Delta logo]()
$519
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/39:54 am
MDW
- HPN
1 stop5h 36m
Delta
Mon 7/612:38 pm
HPN
- MDW
1 stop6h 53m
Delta
Deal found 6/2![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 9/259:30 am
MDW
- HPN
1 stop5h 15m
Delta
Sun 9/2710:29 am
HPN
- MDW
1 stop6h 42m
Delta
Deal found 6/1![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/299:54 am
MDW
- HPN
1 stop5h 36m
Delta
Thu 7/912:36 pm
HPN
- MDW
1 stop6h 49m
Delta
Deal found 6/3![Delta logo]()
$533
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/236:00 am
MDW
- HPN
1 stop5h 08m
Delta
Sun 7/2610:29 am
HPN
- MDW
1 stop6h 46m
Delta
Deal found 6/3![Delta logo]()
$571
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/511:22 am
ORD
- HPN
2 stops10h 03m
Delta
Sat 8/812:36 pm
HPN
- ORD
1 stop4h 41m
Delta
Deal found 5/31![Delta logo]()
$602
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/39:17 am
MDW
- HPN
1 stop5h 32m
Delta
Sun 7/54:29 pm
HPN
- MDW
1 stop6h 48m
Delta
Deal found 6/3![Delta logo]()
$637
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/121:50 pm
ORD
- HPN
1 stop7h 35m
Delta
Thu 8/2012:48 pm
HPN
- ORD
2 stops8h 39m
Delta
Deal found 5/31![Delta logo]()
$642
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/165:30 am
ORD
- HPN
1 stop7h 59m
Delta
Fri 7/245:12 pm
HPN
- ORD
2 stops7h 41m
Delta
Deal found 6/1![Delta logo]()
$656
This Delta deal was found by Cheapflights users on 5/30. 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 6/1311:15 am
ORD
- HPN
2 stops10h 10m
Delta
Mon 6/153:08 pm
HPN
- ORD
1 stop7h 17m
Delta
Deal found 5/30![Delta logo]()
$686
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/212:27 pm
ORD
- HPN
2 stops8h 58m
Delta
Sun 7/56:29 am
HPN
- ORD
1 stop7h 07m
Delta
Deal found 6/2![Delta logo]()
$704
This Delta deal was found by Cheapflights users on 5/29. 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 8/1511:22 am
ORD
- HPN
2 stops10h 03m
Delta
Sat 8/226:00 am
HPN
- ORD
2 stops8h 36m
Delta
Deal found 5/29![Delta logo]()
$709
Last-minute flights from Chicago to Westchester CountyDiscover last-minute flight deals from Chicago to Westchester County. Data last updated June 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Westchester County. Data last updated June 3, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 6/107:37 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Sat 6/135:59 pm
HPN
- ORD
Nonstop2h 54m
American Airlines
Deal found 6/2![American Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 6/106:00 am
MDW
- HPN
1 stop5h 09m
Delta
Sat 6/1312:38 pm
HPN
- MDW
1 stop6h 33m
Delta
Deal found 6/2![Delta logo]()
$475
This American Airlines deal was found by Cheapflights users on 5/30. 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 6/137:29 pm
ORD
- HPN
Nonstop2h 22m
American Airlines
Sat 7/114:30 pm
HPN
- ORD
Nonstop2h 50m
American Airlines
Deal found 5/30![American Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/277:01 am
ORD
- HPN
1 stop3h 57m
Delta
Mon 6/295:10 pm
HPN
- ORD
1 stop20h 54m
Delta
Deal found 6/1![Delta logo]()
$444
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/112:42 pm
ORD
- HPN
Nonstop2h 17m
American Airlines
Wed 7/87:10 am
HPN
- ORD
Nonstop2h 41m
American Airlines
Deal found 6/3![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:01 am
ORD
- HPN
1 stop3h 57m
Delta
Wed 7/84:29 pm
HPN
- ORD
1 stop8h 24m
Delta
Deal found 6/3![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
MDW
- HPN
1 stop5h 14m
Delta
Wed 7/810:29 am
HPN
- MDW
1 stop6h 46m
Delta
Deal found 6/3![Delta logo]()
$415
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:41 pm
ORD
- HPN
Nonstop2h 18m
American Airlines
Mon 7/64:39 pm
HPN
- ORD
Nonstop2h 50m
American Airlines
Deal found 6/3![American Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:19 am
MDW
- HPN
1 stop5h 28m
Delta
Mon 7/134:29 pm
HPN
- MDW
1 stop6h 46m
Delta
Deal found 6/3![Delta logo]()
$459
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:17 pm
ORD
- HPN
1 stop15h 39m
Delta
Sat 7/256:49 pm
HPN
- ORD
1 stop6h 04m
Delta
Deal found 5/31![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:58 pm
MDW
- HPN
1 stop15h 58m
Delta
Sat 7/2512:36 pm
HPN
- MDW
1 stop6h 31m
Delta
Deal found 5/31![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:17 pm
ORD
- HPN
1 stop15h 39m
Delta
Sun 7/266:00 am
HPN
- ORD
1 stop5h 10m
Delta
Deal found 5/31![Delta logo]()
$458
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 June 3, 2026.
Search for one-way flight options from Chicago to Westchester County. Find affordable one-way fares based on user searches. Data last updated June 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/315:30 pm
ORD
- HPN
2 stops40h 50m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/285:13 pm
ORD
- HPN
2 stops17h 07m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/265:30 pm
ORD
- HPN
2 stops26h 30m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/15:30 pm
ORD
- HPN
2 stops16h 50m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/155:13 pm
ORD
- HPN
2 stops17h 14m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/30. 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.
Wed 6/244:59 pm
ORD
- HPN
2 stops17h 28m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/85:13 pm
ORD
- HPN
2 stops17h 14m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/75:13 pm
ORD
- HPN
2 stops17h 07m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 5/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:55 am
ORD
- HPN
3 stops50h 25m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/295:30 pm
ORD
- HPN
2 stops46h 59m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/305:13 pm
ORD
- HPN
2 stops23h 16m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:55 am
ORD
- HPN
2 stops33h 34m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$200
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 June 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $395 (American Airlines) |
One-way from | $139 (Kiwi.com) |
Popular in | May |
Cheapest in | January |
Average price | $252 |
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 June 3, 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
MDW - HPN
MDWHPN
Chicago Midway
Wed 7/1
6:00 am-12:14 pm
1 stop5h 14m
White Plains Westchester County
Wed 7/8
10:29 am-4:15 pm
1 stop6h 46m
$415
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Wed 7/22
7:05 am-3:47 pm
1 stop7h 42m
White Plains Westchester County
Thu 7/30
6:49 pm-11:53 pm
1 stop6h 04m
$458
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Tue 7/21
3:22 pm-10:25 pm
1 stop6h 03m
White Plains Westchester County
Thu 7/30
6:49 pm-11:53 pm
1 stop6h 04m
$459
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Wed 7/8
9:19 am-3:47 pm
1 stop5h 28m
White Plains Westchester County
Mon 7/13
4:29 pm-10:15 pm
1 stop6h 46m
$459
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Thu 8/13
9:24 am-3:48 pm
1 stop5h 24m
White Plains Westchester County
Sun 8/16
6:00 am-9:59 am
1 stop4h 59m
$503
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Thu 7/2
9:17 am-3:49 pm
1 stop5h 32m
White Plains Westchester County
Thu 7/9
10:29 am-4:15 pm
1 stop6h 46m
$503
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 6/6
5:30 am-12:02 pm
1 stop5h 32m
White Plains Westchester County
Sun 6/7
12:38 pm-6:29 pm
1 stop6h 51m
$519
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Fri 7/3
9:54 am-4:30 pm
1 stop5h 36m
White Plains Westchester County
Mon 7/6
12:38 pm-6:31 pm
1 stop6h 53m
$531
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Fri 9/25
9:30 am-3:45 pm
1 stop5h 15m
White Plains Westchester County
Sun 9/27
10:29 am-4:11 pm
1 stop6h 42m
$531
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Mon 6/29
9:54 am-4:30 pm
1 stop5h 36m
White Plains Westchester County
Thu 7/9
12:36 pm-6:25 pm
1 stop6h 49m
$533
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.
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 June 3, 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 May 30, 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.
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 June 3, 2026.
Peruse reviews from past customers who have flown with American Airlines from Chicago to Westchester County to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.2
Overall
7.1
Boarding
7.5
Entertainment
6.9
Crew
7.9
Food
6.4
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Comfort
7.2
Overall
7.1
Boarding
7.5
Entertainment
6.9
Crew
7.9
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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Complete your trip
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Chicago and Westchester County flights
Browse other Chicago and Westchester County flight options. Last updated on June 3, 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 June 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$380 | Average$491 | FlexibilityNo cancel fee | On-time71% |