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Westchester County

$202+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HPN
Aug 10 — Aug 171
Sun 8/10
Sun 8/17
1 adult, Economy
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Cheap 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 August 5, 2025.

Round-trip from

$311
(Delta)

One-way from

$202
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$192
From Chicago O'Hare Intl to Westchester County
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One-way flight from Chicago O'Hare Intl to Westchester County
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Highest demand for flights based on searches. 4% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from O'Hare Intl to Westchester County

Cheapest flights from O'Hare Intl to Westchester County
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 August 5, 2025.

This Delta deal was found by Cheapflights users on 8/5. 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.
Tue 12/167:00 amORD - HPN
1 stop8h 34mDelta
Tue 1/65:10 pmHPN - ORD
1 stop17h 25mDelta
Deal found 8/5$311
This Delta deal was found by Cheapflights users on 8/5. 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.
Tue 12/1611:19 amORD - HPN
1 stop9h 19mDelta
Thu 1/86:00 amHPN - ORD
1 stop11h 39mDelta
Deal found 8/5$313
This Delta deal was found by Cheapflights users on 8/5. 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.
Mon 12/157:55 pmORD - HPN
1 stop15h 16mDelta
Mon 1/56:00 amHPN - ORD
1 stop16h 14mDelta
Deal found 8/5$323
This Delta deal was found by Cheapflights users on 8/5. 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.
Wed 12/179:30 amORD - HPN
1 stop11h 08mDelta
Wed 1/710:29 amHPN - ORD
1 stop9h 28mDelta
Deal found 8/5$338
This American Airlines deal was found by Cheapflights users on 8/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/227:28 pmORD - HPN
Nonstop2h 24mAmerican Airlines
Sat 10/2512:00 pmHPN - ORD
Nonstop2h 35mAmerican Airlines
Deal found 8/5$349
This American Airlines deal was found by Cheapflights users on 8/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:34 pmORD - HPN
Nonstop2h 19mAmerican Airlines
Sun 8/317:24 amHPN - ORD
Nonstop2h 36mAmerican Airlines
Deal found 8/5$350
This Delta deal was found by Cheapflights users on 8/5. 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.
Thu 12/187:00 amORD - HPN
1 stop8h 34mDelta
Tue 1/65:10 pmHPN - ORD
1 stop17h 25mDelta
Deal found 8/5$354
This Delta deal was found by Cheapflights users on 8/5. 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.
Thu 12/187:00 amORD - HPN
1 stop8h 34mDelta
Thu 1/812:45 pmHPN - ORD
1 stop10h 03mDelta
Deal found 8/5$366
This Delta deal was found by Cheapflights users on 8/5. 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.
Wed 10/2210:30 amORD - HPN
1 stop4h 19mDelta
Sat 10/2512:44 pmHPN - ORD
1 stop7h 05mDelta
Deal found 8/5$369
This American Airlines deal was found by Cheapflights users on 8/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:33 pmORD - HPN
Nonstop2h 26mAmerican Airlines
Mon 9/156:00 amHPN - ORD
Nonstop2h 30mAmerican Airlines
Deal found 8/4$380
This American Airlines deal was found by Cheapflights users on 8/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/56:31 pmORD - HPN
Nonstop2h 28mAmerican Airlines
Tue 9/912:00 pmHPN - ORD
Nonstop2h 36mAmerican Airlines
Deal found 8/5$384

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 August 5, 2025.
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

O'Hare Intl

Fly to

Westchester County

Route

Depart

Return

Price

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 12/16

7:00 am-4:34 pm

1 stop8h 34m

White Plains Westchester County

Wed 1/7

12:45 pm-9:48 pm

1 stop10h 03m

$311

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 12/16

11:19 am-9:38 pm

1 stop9h 19m

White Plains Westchester County

Thu 1/8

6:00 am-4:39 pm

1 stop11h 39m

$313

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Mon 12/15

7:55 pm-12:11 pm

1 stop15h 16m

White Plains Westchester County

Tue 1/6

12:59 pm-9:14 pm

1 stop9h 15m

$323

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 12/17

7:10 am-9:38 pm

1 stop13h 28m

White Plains Westchester County

Fri 1/9

12:59 pm-9:14 pm

1 stop9h 15m

$338

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 10/22

7:28 pm-10:52 pm

Nonstop2h 24m

White Plains Westchester County

Sat 10/25

12:00 pm-1:35 pm

Nonstop2h 35m

$349

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 8/30

7:34 pm-10:53 pm

Nonstop2h 19m

White Plains Westchester County

Sun 8/31

7:24 am-9:00 am

Nonstop2h 36m

$350

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 12/18

7:00 am-4:34 pm

1 stop8h 34m

White Plains Westchester County

Wed 1/7

12:45 pm-9:48 pm

1 stop10h 03m

$354

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 12/18

7:00 am-4:34 pm

1 stop8h 34m

White Plains Westchester County

Thu 1/8

12:45 pm-9:48 pm

1 stop10h 03m

$366

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 10/22

10:30 am-3:49 pm

1 stop4h 19m

White Plains Westchester County

Sat 10/25

12:44 pm-6:49 pm

1 stop7h 05m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 9/13

6:33 pm-9:59 pm

Nonstop2h 26m

White Plains Westchester County

Mon 9/15

6:00 am-7:30 am

Nonstop2h 30m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/4

Showing 1-10 of 22 results
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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.
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

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Westchester County?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Westchester County (average of $276). Flying from Chicago O'Hare Intl Airport to Westchester County in March is currently the most expensive (average of $339). 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 August 5, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport to Westchester County as you normally would.

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 August 5, 2025.

The most flights from ORD to zzREU are scheduled on a Monday (7 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (3 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 August 5, 2025.
Read reviews from past customers who have flown Delta and 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.
Delta
8.0
Very good
7,985 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
Delta
8.0
Very good
7,985 reviews
Delta
8.0
Very good
7,985 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,985 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Westchester County. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Westchester County?

    Consider Alaska Airlines (80%), American Airlines (72%) or Envoy Air (72%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Westchester County.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Westchester County?

    Looking at all options, your cheapest flight can be booked for $176. While the most popular route (Chicago O'Hare Intl - White Plains Westchester County) can be booked for $369 on average our data indicates $495 when flying from Chicago O'Hare Intl Airport to Westchester County.

  • Can I find deals for flights from O'Hare Intl to Westchester County that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Westchester County flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Westchester County?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Westchester County.

  • Can I find deals for business class flights from O'Hare Intl to Westchester County?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Westchester County by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Westchester County?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Westchester County (average of $276). Flying from Chicago O'Hare Intl Airport to Westchester County in March is currently the most expensive (average of $339). 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.

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Alternative routes for O'Hare Intl to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
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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 August 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$336Average$452FlexibilityNo cancel feeOn-time71%

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