$123+ Cheap flights from O'Hare Intl (ORD) 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.
ORD — HPN
May 22 — May 291
Round-trip
1 adult, Economy
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Cheapest flights from O'Hare Intl to Westchester CountyExplore the most affordable flight options available from O'Hare Intl to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2026.
Explore the most affordable flight options available from O'Hare Intl to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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
Fri 5/156:09 pm
HPN
- ORD
2 stops19h 14m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/151:59 pm
ORD
- HPN
2 stops20h 21m
Multiple Airlines
Sun 5/178:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 4/301:12 pm
ORD
- HPN
1 stop21h 16m
Multiple Airlines
Mon 5/116:09 pm
HPN
- ORD
2 stops26h 42m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:18 am
ORD
- HPN
Nonstop2h 10m
American Airlines
Sat 8/2212:00 pm
HPN
- ORD
Nonstop2h 36m
American Airlines
Deal found 4/17![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2211:30 am
ORD
- HPN
1 stop4h 03m
Delta
Mon 8/245:10 pm
HPN
- ORD
1 stop15h 46m
Delta
Deal found 4/17![Delta logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/61:59 pm
ORD
- HPN
2 stops30h 00m
Multiple Airlines
Sun 5/108:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 8/157:10 am
ORD
- HPN
1 stop3h 34m
Delta
Sat 8/224:19 pm
HPN
- ORD
1 stop8h 38m
Delta
Deal found 4/20![Delta logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Sun 5/248:00 am
HPN
- ORD
2 stops13h 32m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$421
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/196:04 pm
ORD
- HPN
Nonstop2h 28m
American Airlines
Sat 6/275:46 pm
HPN
- ORD
Nonstop2h 54m
American Airlines
Deal found 4/20![American Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:30 am
ORD
- HPN
1 stop8h 02m
Delta
Mon 8/245:10 pm
HPN
- ORD
1 stop15h 46m
Delta
Deal found 4/17![Delta logo]()
$433
Best flights from O'Hare Intl to Westchester CountyDiscover carefully curated flight deals from O'Hare Intl to Westchester County that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 22, 2026.
Discover carefully curated flight deals from O'Hare Intl to Westchester County that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 22, 2026.
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:30 am
ORD
- HPN
1 stop8h 02m
Delta
Mon 8/245:10 pm
HPN
- ORD
1 stop15h 46m
Delta
Deal found 4/17![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2911:09 am
ORD
- HPN
1 stop3h 40m
Delta
Sun 5/316:00 am
HPN
- ORD
1 stop5h 16m
Delta
Deal found 4/21![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 9/712:59 pm
HPN
- ORD
1 stop8h 18m
Delta
Deal found 4/22![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:15 am
ORD
- HPN
1 stop5h 45m
Delta
Sat 5/96:00 am
HPN
- ORD
1 stop8h 01m
Delta
Deal found 4/17![Delta logo]()
$475
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/27:01 am
ORD
- HPN
1 stop3h 54m
Delta
Sun 7/56:29 am
HPN
- ORD
1 stop7h 07m
Delta
Deal found 4/20![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/42:59 pm
ORD
- HPN
1 stop6h 21m
Delta
Mon 6/86:49 pm
HPN
- ORD
1 stop6h 10m
Delta
Deal found 4/20![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 8/157:10 am
ORD
- HPN
1 stop3h 34m
Delta
Tue 8/1812:45 pm
HPN
- ORD
1 stop4h 51m
Delta
Deal found 4/22![Delta logo]()
$515
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/98:10 am
ORD
- HPN
1 stop5h 19m
Delta
Fri 5/226:40 pm
HPN
- ORD
2 stops15h 05m
Delta
Deal found 4/20![Delta logo]()
$540
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:49 am
ORD
- HPN
1 stop7h 11m
Delta
Sun 5/105:15 pm
HPN
- ORD
1 stop3h 59m
Delta
Deal found 4/17![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/1511:26 am
ORD
- HPN
1 stop5h 34m
Delta
Sun 5/176:00 am
HPN
- ORD
1 stop5h 16m
Delta
Deal found 4/22![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/177:01 am
ORD
- HPN
1 stop3h 54m
Delta
Mon 6/225:10 pm
HPN
- ORD
1 stop4h 21m
Delta
Deal found 4/19![Delta logo]()
$609
Last-minute flights from O'Hare Intl to Westchester CountyDiscover last-minute flight deals from O'Hare Intl to Westchester County. Data last updated April 22, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Westchester County. Data last updated April 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 4/301:12 pm
ORD
- HPN
1 stop21h 16m
Multiple Airlines
Mon 5/116:09 pm
HPN
- ORD
2 stops26h 42m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/61:59 pm
ORD
- HPN
2 stops30h 00m
Multiple Airlines
Sun 5/108:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/81:59 pm
ORD
- HPN
2 stops20h 21m
Multiple Airlines
Sun 5/108:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$395
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:54 pm
ORD
- HPN
1 stop8h 06m
American Airlines
Tue 5/1912:00 pm
HPN
- ORD
Nonstop2h 43m
American Airlines
Deal found 4/19![American Airlines logo]()
$435
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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
Fri 5/156:09 pm
HPN
- ORD
2 stops19h 14m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/151:59 pm
ORD
- HPN
2 stops20h 21m
Multiple Airlines
Sun 5/178:00 am
HPN
- ORD
1 stop7h 39m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Sun 5/248:00 am
HPN
- ORD
2 stops13h 32m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$421
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/1912:42 pm
ORD
- HPN
1 stop6h 45m
American Airlines
Tue 5/267:10 am
HPN
- ORD
Nonstop2h 43m
American Airlines
Deal found 4/19![American Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:00 am
ORD
- HPN
1 stop3h 51m
Delta
Tue 6/96:49 pm
HPN
- ORD
1 stop6h 10m
Delta
Deal found 4/19![Delta logo]()
$415
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:03 pm
ORD
- HPN
Nonstop2h 29m
American Airlines
Sun 5/317:10 am
HPN
- ORD
Nonstop2h 43m
American Airlines
Deal found 4/17![American Airlines logo]()
$429
One-way flights from O'Hare Intl to Westchester CountySearch for one-way flight options from O'Hare Intl to Westchester County. Find affordable one-way fares based on user searches. Data last updated April 22, 2026.
Search for one-way flight options from O'Hare Intl to Westchester County. Find affordable one-way fares based on user searches. Data last updated April 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:39 am
ORD
- HPN
1 stop11h 20m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/151:59 pm
ORD
- HPN
2 stops20h 21m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:59 pm
ORD
- HPN
2 stops26h 30m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/191:59 pm
ORD
- HPN
2 stops20h 21m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:55 am
ORD
- HPN
2 stops27h 25m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:59 pm
ORD
- HPN
3 stops20h 21m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:55 am
ORD
- HPN
2 stops51h 25m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$173
Find flight deals from O'Hare Intl to Westchester County
Keep the following information in mind while searching for O'Hare Intl to Westchester County flight deals. Data was last updated April 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $348 (Kiwi.com) |
One-way from | $123 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $243 |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 22, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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
Thu 8/20
5:30 am-2:32 pm
1 stop8h 02m
White Plains Westchester County
Mon 8/24
5:10 pm-7:56 am
1 stop15h 46m
$433
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Fri 5/29
11:09 am-3:49 pm
1 stop3h 40m
White Plains Westchester County
Sun 5/31
6:00 am-10:16 am
1 stop5h 16m
$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
12:59 pm-8:17 pm
1 stop8h 18m
$449
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 5/2
5:15 am-12:00 pm
1 stop5h 45m
White Plains Westchester County
Sat 5/9
6:00 am-1:01 pm
1 stop8h 01m
$475
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Thu 7/2
7:01 am-11:55 am
1 stop3h 54m
White Plains Westchester County
Sun 7/5
6:29 am-12:36 pm
1 stop7h 07m
$483
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Thu 6/4
2:59 pm-10:20 pm
1 stop6h 21m
White Plains Westchester County
Mon 6/8
6:49 pm-11:59 pm
1 stop6h 10m
$483
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 8/15
7:10 am-11:44 am
1 stop3h 34m
White Plains Westchester County
Tue 8/18
12:45 pm-4:36 pm
1 stop4h 51m
$515
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Sat 5/9
8:10 am-2:29 pm
1 stop5h 19m
White Plains Westchester County
Fri 5/22
6:40 pm-8:45 am
2 stops15h 05m
$540
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Fri 5/8
9:49 am-6:00 pm
1 stop7h 11m
White Plains Westchester County
Sun 5/10
5:15 pm-8:14 pm
1 stop3h 59m
$543
ChicagoWhite Plains
ORD - HPN
ORDHPN
Chicago O'Hare Intl
Fri 5/15
11:26 am-6:00 pm
1 stop5h 34m
White Plains Westchester County
Sun 5/17
6:00 am-10:16 am
1 stop5h 16m
$543
Showing 1-10 of 21 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Westchester County
Have a flexible travel schedule? Discover the best time to fly to Westchester County from O'Hare Intl with our price prediction graph.
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 O'Hare Intl Airport to Westchester County
ORD-zzREU
ORD-HPN
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Westchester County?
Currently, March is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Westchester County (average of $124). Flying from Chicago O'Hare Intl Airport to Westchester County in February is currently the most expensive (average of $449). 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 ORD to REU?
Find hourly flight availability from O'Hare Intl 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 22, 2026.
When flying from Chicago O'Hare Intl Airport to Westchester County, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 5% versus a flight in the afternoon.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Westchester County?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Westchester County. Price data was last updated on April 18, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Westchester County flight should consider departing on Saturday afternoons when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago O'Hare Intl Airport to Westchester County
Explore weekly flight availability from O'Hare Intl to Westchester County. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 22, 2026.
The most flights from ORD to zzREU are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).
Reviews of airlines servicing Westchester County
Get insights into the airlines that provide service to Westchester County. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Westchester County. Reviews last updated April 22, 2026.
Read reviews from past customers who have flown American Airlines from Chicago O'Hare Intl Airport to Westchester County. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.9
Comfort
7.2
Food
6.4
Crew
7.9
Boarding
7.5
Overall
7.1
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Entertainment
6.9
Comfort
7.2
Food
6.4
Crew
7.9
Boarding
7.5
Overall
7.1
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Related info for your journey
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O'Hare Intl and Westchester County flights
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Top airline flying from O'Hare Intl to Westchester County
Discover the top airline that operate flights from O'Hare Intl 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$375 | Average$488 | FlexibilityNo cancel fee | On-time71% |