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O'Hare Intl

$127+ Cheap flights from Westchester County to O'Hare Intl (ORD)

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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — ORD
May 22 — May 291
Fri 5/22
Fri 5/29
1 adult, Economy
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Cheap flight deals from Westchester County to O'Hare Intl

Cheapest flights from Westchester County to O'Hare Intl
Explore the most affordable flight options available from Westchester County to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/21. 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 5/178:00 am
HPN
-
ORD
1 stop7h 39m
Multiple Airlines
Sun 5/175:49 pm
ORD
-
HPN
2 stops22h 40m
Multiple Airlines
Deal found 4/21$382
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Sat 5/912:00 pm
HPN
-
ORD
1 stop27h 39m
Multiple Airlines
Fri 5/151:59 pm
ORD
-
HPN
2 stops20h 21m
Multiple Airlines
Deal found 4/17$385
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Sat 5/1612:00 pm
HPN
-
ORD
1 stop27h 39m
Multiple Airlines
Sun 5/175:49 pm
ORD
-
HPN
2 stops22h 40m
Multiple Airlines
Deal found 4/17$388
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Sun 5/178:00 am
HPN
-
ORD
1 stop7h 39m
Multiple Airlines
Thu 5/218:05 am
ORD
-
HPN
2 stops50h 15m
Multiple Airlines
Deal found 4/17$389
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/148:00 am
HPN
-
ORD
1 stop7h 39m
Multiple Airlines
Fri 5/151:59 pm
ORD
-
HPN
2 stops20h 21m
Multiple Airlines
Deal found 4/18$392
This American Airlines deal was found by Cheapflights users on 4/21. 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 7/117:10 am
HPN
-
ORD
Nonstop2h 42m
American Airlines
Sat 7/2512:41 pm
ORD
-
HPN
Nonstop2h 18m
American Airlines
Deal found 4/21$395
This American Airlines deal was found by Cheapflights users on 4/21. 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 5/237:10 am
HPN
-
ORD
Nonstop2h 43m
American Airlines
Sat 5/306:20 pm
ORD
-
HPN
Nonstop2h 29m
American Airlines
Deal found 4/21$397
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 5/156:09 pm
HPN
-
ORD
2 stops19h 14m
Multiple Airlines
Sun 5/178:39 am
ORD
-
HPN
1 stop11h 20m
Multiple Airlines
Deal found 4/21$400
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Sat 5/912:00 pm
HPN
-
ORD
1 stop27h 39m
Multiple Airlines
Wed 5/1310:49 am
ORD
-
HPN
2 stops31h 11m
Multiple Airlines
Deal found 4/17$410
This Delta deal was found by Cheapflights users on 4/20. 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 7/1112:35 pm
HPN
-
ORD
1 stop4h 48m
Delta
Sat 7/255:15 am
ORD
-
HPN
1 stop8h 14m
Delta
Deal found 4/20$415

Find flight deals from Westchester County to O'Hare Intl

Keep the following information in mind while searching for Westchester County to O'Hare Intl flight deals. Data was last updated April 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$382
(Kiwi.com)

One-way from

$127
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$275
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
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From Westchester County to Chicago O'Hare Intl
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One-way flight from Westchester County to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to O'Hare Intl 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 April 22, 2026.
Use the filters below to find and compare flights from Westchester County to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 6/27

5:10 pm-8:31 pm

1 stop4h 21m

Chicago O'Hare Intl

Wed 7/1

7:01 am-11:55 am

1 stop3h 54m

$415

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 5/23

12:50 pm-6:41 pm

1 stop6h 51m

Chicago O'Hare Intl

Sat 5/30

8:10 am-2:29 pm

1 stop5h 19m

$415

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 8/1

6:29 am-12:37 pm

1 stop7h 08m

Chicago O'Hare Intl

Sat 8/8

7:01 am-11:53 am

1 stop3h 52m

$415
Quickest round-trip

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 5/21

5:15 pm-8:14 pm

1 stop3h 59m

Chicago O'Hare Intl

Mon 5/25

7:00 am-11:51 am

1 stop3h 51m

$511

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 5/8

5:15 pm-8:14 pm

1 stop3h 59m

Chicago O'Hare Intl

Sun 5/10

5:30 am-12:02 pm

1 stop5h 32m

$543

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 5/15

12:30 pm-4:29 pm

1 stop4h 59m

Chicago O'Hare Intl

Sun 5/17

9:25 am-3:49 pm

1 stop5h 24m

$661

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 10/9

3:15 pm-7:34 pm

1 stop5h 19m

Chicago O'Hare Intl

Mon 10/12

11:30 am-4:33 pm

1 stop4h 03m

$671

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 6/18

12:35 pm-6:29 pm

1 stop6h 54m

Chicago O'Hare Intl

Tue 6/23

6:40 am-2:28 pm

1 stop6h 48m

$929

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 7/3

6:49 pm-11:59 pm

1 stop6h 10m

Chicago O'Hare Intl

Sun 7/5

6:30 am-3:49 pm

2 stops8h 19m

$1,169
Cheapest one-way

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 6/17

6:29 am-8:32 pm

1 stop15h 03m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 21 resultsSorted by cheapest first
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Best time to book a flight from Westchester County to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Westchester County 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 Westchester County to Chicago O'Hare Intl Airport

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

Currently, November is the cheapest month in which you can book a flight from Westchester County to Chicago O'Hare Intl Airport (average of $69). Flying from Westchester County to Chicago O'Hare Intl Airport in January is currently the most expensive (average of $375). 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 REU to ORD?

Find hourly flight availability from Westchester County to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 22, 2026.

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

Weekly flight availability from Westchester County to Chicago O'Hare Intl Airport

Explore weekly flight availability from Westchester County to O'Hare Intl. 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 April 22, 2026.

The most flights from zzREU to ORD are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated April 22, 2026.
Peruse reviews from past customers who have flown with American Airlines from Westchester County to Chicago O'Hare Intl Airport to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,647 reviews

Food

6.4

Comfort

7.2

Crew

7.9

Overall

7.1

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.1
Good
11,647 reviews
American Airlines
7.1
Good
11,647 reviews

Food

6.4

Comfort

7.2

Crew

7.9

Overall

7.1

Entertainment

6.9

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Westchester County to O'Hare Intl. 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 Westchester County to Chicago O'Hare Intl Airport?

    Delta can get you from Westchester County to Chicago O'Hare Intl Airport in just under 4h 21m. Your travel time can differ by up to . There are 736 mi between Westchester County and Chicago O'Hare Intl Airport.

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

    The top 3 most reliable airlines when flying from Westchester County to Chicago O'Hare Intl Airport are American Airlines (71%), Envoy Air (71%) and Qatar Airways (67%).

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

    On average you can expect to pay $783 for a flight from Westchester County to Chicago O'Hare Intl Airport. The cheapest flight overall is $158 while the most popular route, (White Plains Westchester County - Chicago O'Hare Intl) is currently priced at $361.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Westchester County to O'Hare Intl 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 Westchester County to Chicago O'Hare Intl Airport?

    Currently, November is the cheapest month in which you can book a flight from Westchester County to Chicago O'Hare Intl Airport (average of $69). Flying from Westchester County to Chicago O'Hare Intl Airport in January is currently the most expensive (average of $375). 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

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Rosemont
Schaumburg
Naperville
Gurnee
Lake Geneva
Delavan
Hoffman Estates
Downers Grove
Oakbrook Terrace
Benton Harbor
Des Plaines
Oak Brook
South Holland
Libertyville
Elgin
Warrenville
Elk Grove Village
Bridgeview
Great Lakes
Lansing

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Top airline flying from Westchester County to O'Hare Intl

Discover the top airline that operate flights from Westchester County to O'Hare Intl. 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 April 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$375Average$493FlexibilityNo cancel feeOn-time71%

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