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Westchester County

$80+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HPN
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$252
(Kiwi.com)

One-way from

$80
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$148
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. 6% potential increase in price ($15 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 January 2026
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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 January 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Sun 2/18:36 pmORD - HPN
2 stops14h 54mMultiple Airlines
Fri 2/2712:08 pmHPN - ORD
1 stop12h 29mMultiple Airlines
Deal found 1/6$252
This American Airlines deal was found by Cheapflights users on 1/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/2810:05 amORD - HPN
1 stop11h 54mAmerican Airlines
Tue 2/107:00 amHPN - ORD
1 stop12h 10mAmerican Airlines
Deal found 1/6$285
This Delta deal was found by Cheapflights users on 1/7. 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 2/165:37 pmORD - HPN
1 stop17h 19mDelta
Thu 2/2612:36 pmHPN - ORD
1 stop9h 08mDelta
Deal found 1/7$329
This Kiwi.com deal was found by Cheapflights users on 1/8. 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 2/207:00 amORD - HPN
2 stops12h 59mMultiple Airlines
Mon 2/2312:08 pmHPN - ORD
1 stop12h 29mMultiple Airlines
Deal found 1/8$334
This American Airlines deal was found by Cheapflights users on 1/7. 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 3/258:14 amORD - HPN
Nonstop2h 15mAmerican Airlines
Sat 3/285:29 pmHPN - ORD
Nonstop2h 48mAmerican Airlines
Deal found 1/7$335
This Delta deal was found by Cheapflights users on 1/7. 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 2/143:21 pmORD - HPN
1 stop5h 39mDelta
Tue 2/2412:36 pmHPN - ORD
1 stop9h 08mDelta
Deal found 1/7$337
This Delta deal was found by Cheapflights users on 1/7. 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 2/145:25 amORD - HPN
1 stop11h 35mDelta
Sat 2/213:15 pmHPN - ORD
1 stop7h 15mDelta
Deal found 1/7$339
This Delta deal was found by Cheapflights users on 1/7. 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 2/1411:18 amORD - HPN
1 stop9h 42mDelta
Mon 2/236:40 pmHPN - ORD
1 stop15h 10mDelta
Deal found 1/7$340
This Delta deal was found by Cheapflights users on 1/6. 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.
Tue 1/2010:35 amORD - HPN
1 stop4h 14mDelta
Tue 1/275:12 pmHPN - ORD
1 stop4h 53mDelta
Deal found 1/6$347
This Delta deal was found by Cheapflights users on 1/6. 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 3/149:35 amORD - HPN
1 stop6h 00mDelta
Sat 3/213:13 pmHPN - ORD
1 stop5h 36mDelta
Deal found 1/6$355
This Delta deal was found by Cheapflights users on 1/6. 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.
Tue 1/279:55 amORD - HPN
1 stop11h 05mDelta
Tue 2/1012:38 pmHPN - ORD
1 stop5h 19mDelta
Deal found 1/6$356

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 January 8, 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

O'Hare Intl

Fly to

Westchester County

Route

Depart

Return

Price

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Mon 2/16

5:37 pm-11:56 am

1 stop17h 19m

White Plains Westchester County

Thu 2/26

12:36 pm-8:44 pm

1 stop9h 08m

$329

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 2/19

6:30 am-3:49 pm

1 stop8h 19m

White Plains Westchester County

Wed 2/25

12:36 pm-8:44 pm

1 stop9h 08m

$329

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 2/18

5:37 pm-11:56 am

1 stop17h 19m

White Plains Westchester County

Thu 2/26

12:36 pm-8:44 pm

1 stop9h 08m

$329

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 2/17

6:30 am-3:49 pm

1 stop8h 19m

White Plains Westchester County

Thu 2/26

12:36 pm-8:44 pm

1 stop9h 08m

$329

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 3/21

7:10 am-11:43 am

1 stop3h 33m

White Plains Westchester County

Mon 3/23

5:17 pm-1:17 pm

1 stop21h 00m

$337

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Mon 2/16

7:41 pm-11:56 am

1 stop15h 15m

White Plains Westchester County

Mon 2/23

5:12 pm-9:41 am

1 stop17h 29m

$339

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 2/19

6:30 am-3:49 pm

1 stop8h 19m

White Plains Westchester County

Mon 2/23

5:12 pm-9:41 am

1 stop17h 29m

$339

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 1/22

5:30 am-2:26 pm

1 stop7h 56m

White Plains Westchester County

Sat 1/24

12:36 pm-4:38 pm

1 stop5h 02m

$347

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/21

5:30 am-12:06 pm

1 stop5h 36m

White Plains Westchester County

Tue 1/27

5:12 pm-9:05 pm

1 stop4h 53m

$347

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 4/1

9:40 am-6:18 pm

1 stop7h 38m

White Plains Westchester County

Wed 4/8

4:29 pm-11:59 pm

1 stop8h 30m

$355

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

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, March is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Westchester County (average of $135). Flying from Chicago O'Hare Intl Airport to Westchester County in November is currently the most expensive (average of $416). 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 January 8, 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 evening.

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 January 3, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Westchester County flight should consider departing on Sunday at noon 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 January 8, 2026.

The most flights from ORD to zzREU are scheduled on a Monday (6 on average). You will have fewer flight options on Friday, 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 January 8, 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.
American Airlines
7.2
Good
11,094 reviews

Crew

8.0

Overall

7.2

Food

6.4

Boarding

7.5

Entertainment

6.9

Comfort

7.2

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
11,094 reviews
American Airlines
7.2
Good
11,094 reviews

Crew

8.0

Overall

7.2

Food

6.4

Boarding

7.5

Entertainment

6.9

Comfort

7.2

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 17h 19m. Delta provides one of the quickest options available for as low as $329. 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 (74%), American Airlines (68%) or Envoy Air (68%) 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 $245. While the most popular route (Chicago O'Hare Intl - White Plains Westchester County) can be booked for $329 on average, our data indicates $465 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, March is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Westchester County (average of $135). Flying from Chicago O'Hare Intl Airport to Westchester County in November is currently the most expensive (average of $416). 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$375Average$476FlexibilityNo cancel feeOn-time71%

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