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Westchester County

$84+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HPN
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
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 November 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$215
(Kiwi.com)

One-way from

$84
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$213
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
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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. 5% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 18, 2025.

This American Airlines deal was found by Cheapflights users on 11/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:10 amORD - HPN
Nonstop2h 19mAmerican Airlines
Wed 12/3112:00 pmHPN - ORD
Nonstop2h 43mAmerican Airlines
Deal found 11/18$349
This American Airlines deal was found by Cheapflights users on 11/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/201:12 pmORD - HPN
1 stop6h 15mAmerican Airlines
Sat 1/176:00 amHPN - ORD
Nonstop2h 52mAmerican Airlines
Deal found 11/18$359
This American Airlines deal was found by Cheapflights users on 11/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:10 amORD - HPN
Nonstop2h 19mAmerican Airlines
Tue 12/304:30 pmHPN - ORD
Nonstop2h 52mAmerican Airlines
Deal found 11/18$380
This American Airlines deal was found by Cheapflights users on 11/17. 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 12/2011:35 amORD - HPN
1 stop5h 48mAmerican Airlines
Mon 12/295:56 pmHPN - ORD
Nonstop2h 47mAmerican Airlines
Deal found 11/17$390
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Wed 12/105:00 amORD - HPN
2 stops30h 39mMultiple Airlines
Fri 12/1212:10 pmHPN - ORD
1 stop9h 32mMultiple Airlines
Deal found 11/18$394
This Delta deal was found by Cheapflights users on 11/17. 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.
Wed 12/317:00 amORD - HPN
1 stop3h 59mDelta
Thu 1/112:55 pmHPN - ORD
1 stop8h 41mDelta
Deal found 11/17$407
This American Airlines deal was found by Cheapflights users on 11/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/201:12 pmORD - HPN
1 stop6h 15mAmerican Airlines
Sat 1/106:00 amHPN - ORD
Nonstop2h 52mAmerican Airlines
Deal found 11/18$409
This American Airlines deal was found by Cheapflights users on 11/17. 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.
Sun 12/218:10 amORD - HPN
Nonstop2h 19mAmerican Airlines
Mon 12/295:56 pmHPN - ORD
Nonstop2h 47mAmerican Airlines
Deal found 11/17$411
This American Airlines deal was found by Cheapflights users on 11/17. 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.
Wed 12/316:30 pmORD - HPN
2 stops19h 00mAmerican Airlines
Sat 1/36:27 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Deal found 11/17$412

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 November 18, 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

Sat 3/14

5:50 am-12:11 pm

1 stop5h 21m

White Plains Westchester County

Tue 3/17

12:45 pm-6:46 pm

1 stop7h 01m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 3/11

7:10 am-2:33 pm

1 stop6h 23m

White Plains Westchester County

Tue 3/17

3:15 pm-7:56 pm

1 stop5h 41m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 1/27

10:35 am-3:49 pm

1 stop4h 14m

White Plains Westchester County

Sat 1/31

3:10 pm-9:43 pm

1 stop7h 33m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/7

6:50 am-11:56 am

1 stop4h 06m

White Plains Westchester County

Sat 1/10

3:10 pm-9:43 pm

1 stop7h 33m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 4/1

7:00 am-11:50 am

1 stop3h 50m

White Plains Westchester County

Wed 4/8

12:45 pm-6:46 pm

1 stop7h 01m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sun 12/21

8:10 am-11:29 am

Nonstop2h 19m

White Plains Westchester County

Tue 12/30

4:30 pm-6:22 pm

Nonstop2h 52m

$380

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 12/20

2:13 pm-5:26 pm

Nonstop2h 13m

White Plains Westchester County

Sat 1/17

6:00 am-7:52 am

Nonstop2h 52m

$399

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 3/14

9:30 am-6:06 pm

1 stop7h 36m

White Plains Westchester County

Sun 3/22

5:10 pm-8:38 pm

1 stop4h 28m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 12/18

5:30 am-12:00 pm

1 stop5h 30m

White Plains Westchester County

Tue 1/6

6:40 pm-11:59 pm

1 stop6h 19m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 12/19

6:45 am-11:59 am

1 stop4h 14m

White Plains Westchester County

Tue 1/6

12:59 pm-7:35 pm

1 stop7h 36m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/16

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, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Westchester County (average of $209). Flying from Chicago O'Hare Intl Airport to Westchester County in September is currently the most expensive (average of $411). 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 November 18, 2025.

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 6% versus a flight in the evening.

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 November 18, 2025.

The most flights from ORD to zzREU are scheduled on a Monday (8 on average). You will have fewer flight options on Friday, 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 November 18, 2025.
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.
American Airlines
7.2
Good
11,045 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Food

6.4

Reviews

1 / 20
6.0
Good

Adwitiya,Sep 2025

DEL - JFK

I recently flew AA’s business class from Delhi to New York, and while the experience ticked the basic boxes, it didn’t quite soar. - Dining: I opted for the vegetarian meal, which was… fine. Not memorable, not offensive—just hovering in the realm of “meh.” The menu could use a refresh with more thoughtful, flavorful options. - Seating: AA seems to be chasing quantity over quality, squeezing in as many business class seats as possible. Yes, they’re lie-flat, but noticeably narrower than what you’d find on other international carriers. Comfort was passable, but not premium. Overall, I’d call it “business class lite.” It gets the job done, but lacks the finesse and attention to detail that elevate a journey. A few strategic tweaks—better food, more spacious seating, and a touch more hospitality—could make a world of difference.
American Airlines
7.2
Good
11,045 reviews
American Airlines
7.2
Good
11,045 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Food

6.4

Reviews

1 / 20
6.0
Good

Adwitiya,Sep 2025

DEL - JFK

I recently flew AA’s business class from Delhi to New York, and while the experience ticked the basic boxes, it didn’t quite soar. - Dining: I opted for the vegetarian meal, which was… fine. Not memorable, not offensive—just hovering in the realm of “meh.” The menu could use a refresh with more thoughtful, flavorful options. - Seating: AA seems to be chasing quantity over quality, squeezing in as many business class seats as possible. Yes, they’re lie-flat, but noticeably narrower than what you’d find on other international carriers. Comfort was passable, but not premium. Overall, I’d call it “business class lite.” It gets the job done, but lacks the finesse and attention to detail that elevate a journey. A few strategic tweaks—better food, more spacious seating, and a touch more hospitality—could make a world of difference.

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.

  • How long is the flight from Chicago O'Hare Intl Airport to Westchester County?

    A quick flight from Chicago O'Hare Intl Airport to Westchester County can take about 5h 21m. Delta provides one of the quickest options available for as low as $369. There are 736 mi between Chicago O'Hare Intl Airport and Westchester County.

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

    Consider Qatar Airways (84%), Alaska Airlines (80%) or American Airlines (79%) 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 $288. While the most popular route (Chicago O'Hare Intl - White Plains Westchester County) can be booked for $275 on average, our data indicates $510 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, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Westchester County (average of $209). Flying from Chicago O'Hare Intl Airport to Westchester County in September is currently the most expensive (average of $411). 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 November 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$374Average$465FlexibilityNo cancel feeOn-time71%

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