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Westchester County

$95+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HPN
Apr 5 — Apr 121
Sun 4/5
Sun 4/12
1 adult, Economy
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Cheap 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 March 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/2. 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 5/151:12 pm
ORD
-
HPN
1 stop21h 05m
Multiple Airlines
Mon 5/186:09 pm
HPN
-
ORD
1 stop6h 07m
Multiple Airlines
Deal found 3/2$206
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 5/141:12 pm
ORD
-
HPN
1 stop27h 17m
Multiple Airlines
Mon 5/186:09 pm
HPN
-
ORD
1 stop6h 07m
Multiple Airlines
Deal found 3/3$237
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 4/231:12 pm
ORD
-
HPN
1 stop21h 16m
Multiple Airlines
Mon 4/2712:08 pm
HPN
-
ORD
2 stops29h 52m
Multiple Airlines
Deal found 3/3$277
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 4/1412:45 pm
ORD
-
HPN
2 stops23h 02m
Multiple Airlines
Mon 4/2012:08 pm
HPN
-
ORD
1 stop11h 58m
Multiple Airlines
Deal found 3/2$298

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 March 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$206
(Kiwi.com)

One-way from

$95
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$221
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 ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in March 2026
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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 March 6, 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

Price

Cheapest round-trip
Quickest round-trip

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 6/9

7:10 am-11:44 am

1 stop3h 34m

White Plains Westchester County

Mon 6/29

5:10 pm-8:24 pm

1 stop4h 14m

$429

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 4/18

7:00 am-11:49 am

1 stop3h 49m

White Plains Westchester County

Sun 4/19

5:20 pm-8:40 pm

1 stop4h 20m

$429

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Mon 8/10

10:35 am-4:33 pm

1 stop4h 58m

White Plains Westchester County

Wed 8/19

12:45 pm-4:36 pm

1 stop4h 51m

$429

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 4/10

7:10 am-11:53 am

1 stop3h 43m

White Plains Westchester County

Sun 4/12

5:17 pm-8:23 pm

1 stop4h 06m

$443

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 4/3

7:10 am-11:53 am

1 stop3h 43m

White Plains Westchester County

Fri 4/10

12:35 pm-6:34 pm

1 stop6h 59m

$463

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 8/13

7:10 am-11:44 am

1 stop3h 34m

White Plains Westchester County

Mon 8/17

3:15 pm-9:34 pm

1 stop7h 19m

$463

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 3/25

8:55 am-4:37 pm

1 stop6h 42m

White Plains Westchester County

Sun 3/29

12:35 pm-6:34 pm

1 stop6h 59m

$469

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sun 8/9

6:00 am-12:14 pm

1 stop5h 14m

White Plains Westchester County

Sun 8/16

3:15 pm-7:43 pm

1 stop5h 28m

$491

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 3/19

5:30 am-12:03 pm

1 stop5h 33m

White Plains Westchester County

Sun 3/22

6:00 am-1:38 pm

1 stop8h 38m

$503

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 3/27

7:10 am-11:53 am

1 stop3h 43m

White Plains Westchester County

Sun 3/29

12:35 pm-6:34 pm

1 stop6h 59m

$503

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/4

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $155). Flying from Chicago O'Hare Intl Airport to Westchester County in February is currently the most expensive (average of $456). 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 March 6, 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 February 21, 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.

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 March 6, 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
7.1
Good
11,392 reviews

Food

6.4

Overall

7.1

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

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
7.1
Good
11,392 reviews
American Airlines
7.1
Good
11,392 reviews

Food

6.4

Overall

7.1

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

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 3h 34m. Delta provides one of the quickest options available for as low as $429. 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 American Airlines (80%), Envoy Air (80%) or Alaska Airlines (76%) 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 $243. While the most popular route (Chicago O'Hare Intl - White Plains Westchester County) can be booked for $230 on average, our data indicates $416 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 $155). Flying from Chicago O'Hare Intl Airport to Westchester County in February is currently the most expensive (average of $456). 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.

See more FAQs

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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 March 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$375Average$479FlexibilityNo cancel feeOn-time71%

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