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O'Hare Intl

$89+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — ORD
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
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 December 14, 2025.

This American Airlines deal was found by Cheapflights users on 12/11. 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.
Tue 12/306:27 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Wed 1/2112:51 pmORD - HPN
Nonstop2h 08mAmerican Airlines
Deal found 12/11$399
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Tue 12/306:27 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Tue 1/2011:29 amORD - HPN
1 stop5h 39mAmerican Airlines
Deal found 12/11$409
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/276:29 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Tue 12/306:39 pmORD - HPN
Nonstop2h 20mAmerican Airlines
Deal found 12/11$449
This American Airlines deal was found by Cheapflights users on 12/12. 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 12/276:29 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Wed 12/311:27 pmORD - HPN
1 stop6h 00mAmerican Airlines
Deal found 12/12$459
This American Airlines deal was found by Cheapflights users on 12/14. 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 12/205:56 pmHPN - ORD
Nonstop2h 47mAmerican Airlines
Sun 12/216:39 pmORD - HPN
Nonstop2h 20mAmerican Airlines
Deal found 12/14$486
This American Airlines deal was found by Cheapflights users on 12/13. 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 12/246:29 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Sun 12/288:10 amORD - HPN
Nonstop2h 19mAmerican Airlines
Deal found 12/13$491
This American Airlines deal was found by Cheapflights users on 12/13. 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 12/206:56 pmHPN - ORD
1 stop6h 03mAmerican Airlines
Tue 12/238:03 amORD - HPN
1 stop7h 43mAmerican Airlines
Deal found 12/13$506
This American Airlines deal was found by Cheapflights users on 12/13. 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.
Fri 12/196:29 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Sun 12/216:39 pmORD - HPN
Nonstop2h 20mAmerican Airlines
Deal found 12/13$523

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 December 14, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$349
(American Airlines)

One-way from

$89
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$272
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
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Highest demand for flights based on searches. 8% potential increase in price ($22 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 December 2025
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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 December 14, 2025.
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

Westchester County

Fly to

O'Hare Intl

Route

Depart

Return

Price

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 2/4

6:00 am-7:52 am

Nonstop2h 52m

Chicago O'Hare Intl

Sat 2/7

6:05 am-1:00 pm

1 stop5h 55m

$359

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 1/28

12:00 pm-1:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 2/4

9:45 am-2:39 pm

1 stop3h 54m

$360

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 4/7

3:12 pm-7:59 pm

1 stop5h 47m

Chicago O'Hare Intl

Sat 4/11

2:25 pm-10:07 pm

1 stop6h 42m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 2/4

12:38 pm-4:57 pm

1 stop5h 19m

Chicago O'Hare Intl

Sat 2/7

8:50 am-4:35 pm

1 stop6h 45m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 4/29

12:45 pm-4:36 pm

1 stop4h 51m

Chicago O'Hare Intl

Sat 5/2

6:00 am-12:14 pm

1 stop5h 14m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 1/28

12:59 pm-7:21 pm

1 stop7h 22m

Chicago O'Hare Intl

Wed 2/4

5:30 am-12:06 pm

1 stop5h 36m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 3/24

12:48 pm-7:52 pm

1 stop8h 04m

Chicago O'Hare Intl

Sat 3/28

6:30 am-11:43 am

1 stop4h 13m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 3/12

12:23 pm-6:42 pm

1 stop7h 19m

Chicago O'Hare Intl

Sat 3/14

8:55 am-3:49 pm

1 stop5h 54m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 3/21

3:12 pm-7:59 pm

1 stop5h 47m

Chicago O'Hare Intl

Sun 3/29

6:30 am-11:43 am

1 stop4h 13m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 1/12

6:00 am-7:52 am

Nonstop2h 52m

Chicago O'Hare Intl

Mon 1/19

8:18 am-11:28 am

Nonstop2h 10m

$411

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

Showing 1-10 of 21 results
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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, February is the cheapest month in which you can book a flight from Westchester County to Chicago O'Hare Intl Airport (average of $300). Flying from Westchester County to Chicago O'Hare Intl Airport in October is currently the most expensive (average of $380). 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 December 14, 2025.

It’s optimal to fly from Westchester County to Chicago O'Hare Intl Airport in the evening. By choosing this option you can save up to 56% on the cost of your flight, compared to a flight in the morning.

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 December 14, 2025.

The most flights from zzREU to ORD are scheduled on a Monday (9 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 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 December 14, 2025.
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
7.2
Good
11,054 reviews

Food

6.5

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

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
7.2
Good
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Food

6.5

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

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?

    American Airlines and Delta can get you from Westchester County to Chicago O'Hare Intl Airport in just under 2h 52m. Your travel time can differ by up to 2h 55m. There are 736 mi between Westchester County and Chicago O'Hare Intl Airport. This flight may include one or multiple stops.

  • 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 (72%), Envoy Air (72%) and Qatar Airways (66%).

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

    On average you can expect to pay $654 for a flight from Westchester County to Chicago O'Hare Intl Airport. The cheapest flight overall is $169 while the most popular route, (White Plains Westchester County - Chicago O'Hare Intl) is currently priced at $267.

  • 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, February is the cheapest month in which you can book a flight from Westchester County to Chicago O'Hare Intl Airport (average of $300). Flying from Westchester County to Chicago O'Hare Intl Airport in October is currently the most expensive (average of $380). 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
Schaumburg
Rosemont
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Warrenville
Waukegan
Aurora
Kenosha
Evanston

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Alternative routes for Westchester County to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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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 December 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$351Average$477FlexibilityNo cancel feeOn-time71%

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