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Westchester County

$118+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HPN
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
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 September 19, 2025.

Round-trip from

$257
(Delta)

One-way from

$118
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$187
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. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 19, 2025.

This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/178:50 amORD - HPN
1 stop6h 44mDelta
Thu 11/2712:55 pmHPN - ORD
1 stop4h 41mDelta
Deal found 9/18$257
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/112:47 pmORD - HPN
2 stops20h 47mMultiple Airlines
Mon 11/1712:10 pmHPN - ORD
1 stop12h 18mMultiple Airlines
Deal found 9/16$268
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:10 amORD - HPN
1 stop3h 49mDelta
Sun 11/96:41 pmHPN - ORD
1 stop6h 20mDelta
Deal found 9/18$277
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/211:36 amORD - HPN
1 stop22h 52mMultiple Airlines
Mon 10/68:25 amHPN - ORD
2 stops34h 28mMultiple Airlines
Deal found 9/17$294
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/198:55 amORD - HPN
2 stops12h 14mDelta
Tue 11/253:08 pmHPN - ORD
1 stop7h 28mDelta
Deal found 9/18$300
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/232:41 pmORD - HPN
1 stop19h 47mMultiple Airlines
Mon 10/271:20 pmHPN - ORD
2 stops31h 43mMultiple Airlines
Deal found 9/17$311
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Thu 10/162:41 pmORD - HPN
1 stop19h 47mMultiple Airlines
Mon 10/208:25 amHPN - ORD
2 stops33h 48mMultiple Airlines
Deal found 9/18$312
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 11/71:50 pmORD - HPN
2 stops20h 23mMultiple Airlines
Mon 11/1012:10 pmHPN - ORD
1 stop12h 18mMultiple Airlines
Deal found 9/18$325
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/162:41 pmORD - HPN
1 stop19h 47mMultiple Airlines
Thu 10/231:19 pmHPN - ORD
2 stops28h 54mMultiple Airlines
Deal found 9/16$330
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:03 pmORD - HPN
1 stop18h 07mDelta
Sun 12/76:00 amHPN - ORD
1 stop5h 20mDelta
Deal found 9/18$332
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/226:45 amORD - HPN
1 stop4h 22mDelta
Mon 11/243:08 pmHPN - ORD
1 stop7h 28mDelta
Deal found 9/18$337
This Delta deal was found by Cheapflights users on 9/17. 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 11/276:45 amORD - HPN
2 stops14h 24mDelta
Tue 12/25:17 pmHPN - ORD
1 stop15h 47mDelta
Deal found 9/17$338

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 September 19, 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

Thu 11/20

5:32 am-11:59 am

1 stop5h 27m

White Plains Westchester County

Tue 11/25

3:08 pm-9:36 pm

1 stop7h 28m

$257

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Mon 11/17

6:45 am-2:28 pm

1 stop6h 43m

White Plains Westchester County

Tue 11/25

3:08 pm-9:36 pm

1 stop7h 28m

$257

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 10/22

11:23 am-6:00 pm

1 stop5h 37m

White Plains Westchester County

Sat 10/25

5:20 pm-8:23 pm

1 stop4h 03m

$277

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 10/16

7:10 am-11:59 am

1 stop3h 49m

White Plains Westchester County

Mon 10/20

4:29 pm-9:24 pm

1 stop5h 55m

$277

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 11/7

7:10 am-11:59 am

1 stop3h 49m

White Plains Westchester County

Mon 11/10

5:14 pm-8:29 pm

1 stop4h 15m

$277

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 12/16

5:32 am-11:59 am

1 stop5h 27m

White Plains Westchester County

Sat 1/17

6:00 am-1:23 pm

1 stop8h 23m

$277

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 12/5

6:45 am-12:10 pm

1 stop4h 25m

White Plains Westchester County

Sun 12/7

6:00 am-10:20 am

1 stop5h 20m

$337

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 11/27

6:45 am-10:09 pm

2 stops14h 24m

White Plains Westchester County

Tue 12/2

5:17 pm-8:04 am

1 stop15h 47m

$338

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 11/18

8:55 am-10:09 pm

2 stops12h 14m

White Plains Westchester County

Tue 11/25

3:08 pm-9:36 pm

1 stop7h 28m

$356

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 11/18

6:45 am-3:49 pm

1 stop8h 04m

White Plains Westchester County

Mon 11/24

6:41 pm-12:02 am

1 stop6h 21m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

Showing 1-10 of 21 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 $338). 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 September 19, 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 September 19, 2025.

The most flights from ORD to zzREU are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 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 September 19, 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
10,000 reviews

Entertainment

6.9

Comfort

7.2

Overall

7.2

Boarding

7.5

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Comfort

7.2

Overall

7.2

Boarding

7.5

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 27m. Delta provides one of the quickest options available for as low as $257. 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 Alaska Airlines (84%), Qatar Airways (78%) or American Airlines (77%) 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 $144. While the most popular route (Chicago O'Hare Intl - White Plains Westchester County) can be booked for $250 on average, our data indicates $517 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 $338). 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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$358Average$459FlexibilityNo cancel feeOn-time71%

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