$114+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
May 7 — May 141
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 April 7, 2026.
Explore the most affordable flight options available from Chicago to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Sun 5/178:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Mon 5/116:09 pm
HPN
- ORD
2 stops29h 05m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:30 pm
ORD
- HPN
2 stops16h 50m
Multiple Airlines
Sun 5/178:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:12 pm
ORD
- HPN
1 stop21h 16m
Multiple Airlines
Mon 4/278:00 am
HPN
- ORD
2 stops30h 00m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Tue 5/1912:27 pm
HPN
- ORD
2 stops11h 46m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:45 pm
ORD
- HPN
2 stops22h 44m
Multiple Airlines
Sun 5/108:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 4/3. 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.
Thu 5/78:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Fri 5/86:09 pm
HPN
- ORD
2 stops29h 05m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$378
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/69:23 am
MDW
- HPN
1 stop6h 12m
Delta
Tue 6/912:35 pm
HPN
- MDW
1 stop6h 56m
Delta
Deal found 4/5![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:46 am
MDW
- HPN
1 stop5h 54m
Delta
Sat 5/164:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Deal found 4/4![Delta logo]()
$445
This Delta deal was found by Cheapflights users on 4/3. 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 9/29:30 am
MDW
- HPN
1 stop6h 03m
Delta
Sun 9/64:19 pm
HPN
- MDW
1 stop6h 27m
Delta
Deal found 4/3![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/3. 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 4/189:46 am
MDW
- HPN
1 stop5h 54m
Delta
Wed 4/224:29 pm
HPN
- MDW
1 stop6h 59m
Delta
Deal found 4/3![Delta logo]()
$475
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/139:17 am
MDW
- HPN
1 stop5h 32m
Delta
Sun 6/1410:29 am
HPN
- MDW
1 stop6h 47m
Delta
Deal found 4/6![Delta logo]()
$477
Best flights from Chicago to Westchester CountyDiscover carefully curated flight deals from Chicago to Westchester County that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 7, 2026.
Discover carefully curated flight deals from Chicago to Westchester County that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 7, 2026.
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 8/2211:30 am
ORD
- HPN
1 stop4h 03m
Delta
Wed 8/2612:59 pm
HPN
- ORD
1 stop6h 40m
Delta
Deal found 4/5![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/69:23 am
MDW
- HPN
1 stop6h 12m
Delta
Tue 6/912:35 pm
HPN
- MDW
1 stop6h 56m
Delta
Deal found 4/5![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/3. 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 5/27:00 am
ORD
- HPN
1 stop3h 49m
Delta
Sat 5/96:00 am
HPN
- ORD
1 stop8h 01m
Delta
Deal found 4/3![Delta logo]()
$445
This Delta deal was found by Cheapflights users on 4/2. 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 6/197:01 am
ORD
- HPN
1 stop3h 54m
Delta
Sat 6/275:10 pm
HPN
- ORD
1 stop4h 21m
Delta
Deal found 4/2![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 9/57:10 am
ORD
- HPN
1 stop6h 22m
Delta
Mon 9/76:40 pm
HPN
- ORD
1 stop6h 17m
Delta
Deal found 4/5![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/137:01 am
ORD
- HPN
1 stop3h 54m
Delta
Sun 6/146:29 am
HPN
- ORD
1 stop7h 07m
Delta
Deal found 4/6![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 6/189:17 am
MDW
- HPN
1 stop5h 32m
Delta
Wed 6/244:29 pm
HPN
- MDW
1 stop6h 48m
Delta
Deal found 4/4![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/3. 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 9/29:30 am
MDW
- HPN
1 stop6h 03m
Delta
Sun 9/64:19 pm
HPN
- MDW
1 stop6h 27m
Delta
Deal found 4/3![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/139:17 am
MDW
- HPN
1 stop5h 32m
Delta
Sun 6/1410:29 am
HPN
- MDW
1 stop6h 47m
Delta
Deal found 4/6![Delta logo]()
$477
This Delta deal was found by Cheapflights users on 4/2. 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 7/23:22 pm
ORD
- HPN
1 stop6h 03m
Delta
Sun 7/56:29 am
HPN
- ORD
1 stop7h 07m
Delta
Deal found 4/2![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 4/3. 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 9/36:00 am
MDW
- HPN
1 stop5h 13m
Delta
Sun 9/612:45 pm
HPN
- MDW
1 stop6h 46m
Delta
Deal found 4/3![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:22 am
MDW
- HPN
1 stop5h 27m
Delta
Sun 5/316:00 am
HPN
- MDW
1 stop6h 56m
Delta
Deal found 4/6![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 4/3. 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
Mon 7/612:35 pm
HPN
- MDW
1 stop6h 56m
Delta
Deal found 4/3![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 4/2. 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 7/246:05 am
MDW
- HPN
1 stop7h 24m
Delta
Sun 7/2612:35 pm
HPN
- MDW
1 stop6h 50m
Delta
Deal found 4/2![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:22 am
MDW
- HPN
1 stop5h 27m
Delta
Mon 5/256:00 am
HPN
- MDW
1 stop6h 56m
Delta
Deal found 4/4![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 4/3. 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 6/189:17 am
MDW
- HPN
1 stop5h 32m
Delta
Mon 6/2212:35 pm
HPN
- MDW
1 stop6h 56m
Delta
Deal found 4/3![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 4/2. 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 4/179:27 am
MDW
- HPN
1 stop5h 22m
Delta
Tue 4/2112:30 pm
HPN
- MDW
1 stop6h 28m
Delta
Deal found 4/2![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/46:23 am
MDW
- HPN
1 stop7h 06m
Delta
Sun 6/712:35 pm
HPN
- MDW
1 stop6h 56m
Delta
Deal found 4/6![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/177:00 am
ORD
- HPN
1 stop3h 49m
Delta
Sun 4/196:00 am
HPN
- ORD
1 stop8h 14m
Delta
Deal found 4/6![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/247:00 am
ORD
- HPN
1 stop3h 49m
Delta
Sun 4/263:10 pm
HPN
- ORD
1 stop7h 28m
Delta
Deal found 4/6![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/2411:00 am
ORD
- HPN
1 stop3h 49m
Delta
Mon 4/2712:48 pm
HPN
- ORD
1 stop8h 28m
Delta
Deal found 4/4![Delta logo]()
$543
Last-minute flights from Chicago to Westchester CountyDiscover last-minute flight deals from Chicago to Westchester County. Data last updated April 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Westchester County. Data last updated April 7, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/2. 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 4/179:27 am
MDW
- HPN
1 stop5h 22m
Delta
Tue 4/2112:30 pm
HPN
- MDW
1 stop6h 28m
Delta
Deal found 4/2![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:46 am
MDW
- HPN
1 stop5h 54m
Delta
Sat 5/164:29 pm
HPN
- MDW
1 stop5h 40m
Delta
Deal found 4/4![Delta logo]()
$445
This Delta deal was found by Cheapflights users on 4/3. 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 4/189:46 am
MDW
- HPN
1 stop5h 54m
Delta
Wed 4/224:29 pm
HPN
- MDW
1 stop6h 59m
Delta
Deal found 4/3![Delta logo]()
$475
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:12 pm
ORD
- HPN
1 stop21h 16m
Multiple Airlines
Mon 4/278:00 am
HPN
- ORD
2 stops30h 00m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Mon 5/116:09 pm
HPN
- ORD
2 stops29h 05m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:45 pm
ORD
- HPN
2 stops22h 44m
Multiple Airlines
Sun 5/108:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 4/3. 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.
Thu 5/78:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Fri 5/86:09 pm
HPN
- ORD
2 stops29h 05m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Sun 5/178:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:30 pm
ORD
- HPN
2 stops16h 50m
Multiple Airlines
Sun 5/178:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Tue 5/1912:27 pm
HPN
- ORD
2 stops11h 46m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:22 am
MDW
- HPN
1 stop5h 27m
Delta
Mon 5/256:00 am
HPN
- MDW
1 stop6h 56m
Delta
Deal found 4/4![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:22 am
MDW
- HPN
1 stop5h 27m
Delta
Sun 5/316:00 am
HPN
- MDW
1 stop6h 56m
Delta
Deal found 4/6![Delta logo]()
$483
One-way flights from Chicago to Westchester CountySearch for one-way flight options from Chicago to Westchester County. Find affordable one-way fares based on user searches. Data last updated April 7, 2026.
Search for one-way flight options from Chicago to Westchester County. Find affordable one-way fares based on user searches. Data last updated April 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:28 am
ORD
- HPN
2 stops23h 00m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 8/2612:04 pm
MDW
- HPN
2 stops31h 55m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- HPN
2 stops31h 55m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:28 am
ORD
- HPN
3 stops23h 00m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:26 am
MDW
- HPN
2 stops26h 02m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:45 pm
ORD
- HPN
2 stops22h 44m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:15 pm
MDW
- HPN
2 stops20h 13m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/3. 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.
Wed 4/2911:28 am
ORD
- HPN
3 stops30h 47m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 6/38:05 am
ORD
- HPN
2 stops35h 54m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 4/2811:28 am
ORD
- HPN
2 stops24h 19m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/206:40 am
ORD
- HPN
2 stops27h 48m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$140
Find flight deals from Chicago to Westchester County
Keep the following information in mind while searching for Chicago to Westchester County flight deals. Data was last updated April 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $265 (Kiwi.com) |
One-way from | $114 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $229 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Westchester County that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 7, 2026.
Use the filters below to find and compare flights from Chicago to Westchester County that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 8/22
11:30 am-4:33 pm
1 stop4h 03m
White Plains Westchester County
Wed 8/26
12:59 pm-6:39 pm
1 stop6h 40m
$415
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Sat 6/6
9:23 am-4:35 pm
1 stop6h 12m
White Plains Westchester County
Tue 6/9
12:35 pm-6:31 pm
1 stop6h 56m
$415
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 5/2
7:00 am-11:49 am
1 stop3h 49m
White Plains Westchester County
Sat 5/9
6:00 am-1:01 pm
1 stop8h 01m
$445
Quickest round-trip
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Fri 6/19
7:01 am-11:55 am
1 stop3h 54m
White Plains Westchester County
Sat 6/27
5:10 pm-8:31 pm
1 stop4h 21m
$449
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 9/5
7:10 am-2:32 pm
1 stop6h 22m
White Plains Westchester County
Mon 9/7
6:40 pm-11:57 pm
1 stop6h 17m
$449
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 6/13
7:01 am-11:55 am
1 stop3h 54m
White Plains Westchester County
Sun 6/14
6:29 am-12:36 pm
1 stop7h 07m
$449
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Thu 6/18
9:17 am-3:49 pm
1 stop5h 32m
White Plains Westchester County
Wed 6/24
4:29 pm-10:17 pm
1 stop6h 48m
$449
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Wed 9/2
9:30 am-4:33 pm
1 stop6h 03m
White Plains Westchester County
Sun 9/6
4:19 pm-9:46 pm
1 stop6h 27m
$449
ChicagoWhite Plains
MDW - HPN
MDWHPN
Chicago Midway
Sat 6/13
9:17 am-3:49 pm
1 stop5h 32m
White Plains Westchester County
Sun 6/14
10:29 am-4:16 pm
1 stop6h 47m
$477
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Thu 7/2
3:22 pm-10:25 pm
1 stop6h 03m
White Plains Westchester County
Sun 7/5
6:29 am-12:36 pm
1 stop7h 07m
$483
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 $459). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to REU?
Find hourly flight availability from Chicago to Westchester County. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 7, 2026.
One of the essential ways to save on airfare from Chicago to Westchester County is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 5% on airfare.
What is the cheapest day to fly from Chicago to Westchester County?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Westchester County. Price data was last updated on April 4, 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 April 7, 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
6.9
Boarding
7.5
Food
6.4
Overall
7.1
Crew
7.9
Comfort
7.2
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Entertainment
6.9
Boarding
7.5
Food
6.4
Overall
7.1
Crew
7.9
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 April 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Chicago to Westchester County
Discover the top airline that operate flights from Chicago to Westchester County. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$375 | Average$485 | FlexibilityNo cancel fee | On-time71% |