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O'Hare Intl

$202+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — ORD
Aug 10 — Aug 171
Sun 8/10
Sun 8/17
1 adult, Economy
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Cheap 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 August 5, 2025.

Round-trip from

$359
(American Airlines)

One-way from

$202
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$247
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. 12% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 5, 2025.

This American Airlines deal was found by Cheapflights users on 8/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1711:15 amHPN - ORD
1 stop7h 08mAmerican Airlines
Wed 9/248:15 amORD - HPN
Nonstop2h 14mAmerican Airlines
Deal found 8/3$359
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:00 amHPN - ORD
1 stop8h 01mDelta
Wed 9/247:20 amORD - HPN
1 stop6h 09mDelta
Deal found 8/3$369
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:00 amHPN - ORD
2 stops15h 23mDelta
Sat 9/67:15 amORD - HPN
1 stop7h 34mDelta
Deal found 8/3$375
This American Airlines deal was found by Cheapflights users on 8/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1012:00 pmHPN - ORD
Nonstop2h 36mAmerican Airlines
Mon 9/1512:49 pmORD - HPN
Nonstop2h 10mAmerican Airlines
Deal found 8/3$379
This American Airlines deal was found by Cheapflights users on 8/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1112:00 pmHPN - ORD
Nonstop2h 35mAmerican Airlines
Mon 10/137:28 pmORD - HPN
Nonstop2h 24mAmerican Airlines
Deal found 8/3$380
This KAYAK deal was found by Cheapflights users on 8/4. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/225:29 pmHPN - ORD
2 stops17h 46mAmerican Airlines
Sat 8/2312:49 pmORD - HPN
Nonstop2h 10mAmerican Airlines
Deal found 8/4$409
This American Airlines deal was found by Cheapflights users on 8/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:20 amHPN - ORD
Nonstop2h 36mAmerican Airlines
Sun 10/266:29 pmORD - HPN
Nonstop2h 30mAmerican Airlines
Deal found 8/3$411
This American Airlines deal was found by Cheapflights users on 8/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/277:01 amHPN - ORD
Nonstop2h 32mAmerican Airlines
Sat 10/48:15 amORD - HPN
Nonstop2h 14mAmerican Airlines
Deal found 8/3$419

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 August 5, 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 9/17

11:15 am-5:23 pm

1 stop7h 08m

Chicago O'Hare Intl

Wed 9/24

8:15 am-11:29 am

Nonstop2h 14m

$359

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 9/17

6:00 am-1:01 pm

1 stop8h 01m

Chicago O'Hare Intl

Wed 9/24

7:20 am-2:29 pm

1 stop6h 09m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 9/4

6:00 am-8:23 pm

2 stops15h 23m

Chicago O'Hare Intl

Sat 9/6

7:15 am-3:49 pm

1 stop7h 34m

$375

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 9/10

12:00 pm-1:36 pm

Nonstop2h 36m

Chicago O'Hare Intl

Mon 9/15

12:49 pm-3:59 pm

Nonstop2h 10m

$379

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 10/11

12:00 pm-1:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Mon 10/13

7:28 pm-10:52 pm

Nonstop2h 24m

$380

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 8/22

5:29 pm-10:15 am

2 stops17h 46m

Chicago O'Hare Intl

Sat 8/23

12:49 pm-3:59 pm

Nonstop2h 10m

$409

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 10/24

6:00 am-7:36 am

Nonstop2h 36m

Chicago O'Hare Intl

Mon 10/27

2:09 pm-5:27 pm

Nonstop2h 18m

$411

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 9/27

7:01 am-8:33 am

Nonstop2h 32m

Chicago O'Hare Intl

Sat 10/4

8:15 am-11:29 am

Nonstop2h 14m

$419

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 10/1

6:30 am-6:10 pm

2 stops12h 40m

$202

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sun 8/31

5:29 pm-6:47 am

2 stops14h 18m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/3

Showing 1-10 of 20 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, August is the cheapest month in which you can book a flight from Westchester County to Chicago O'Hare Intl Airport (average of $245). Flying from Westchester County to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 August 5, 2025.

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.

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 August 5, 2025.
Peruse reviews from past customers who have flown with Delta and 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.
Delta
8.0
Very good
7,987 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,987 reviews
Delta
8.0
Very good
7,987 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,987 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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.

  • 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 Alaska Airlines (76%), American Airlines (75%) and Envoy Air (75%).

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

    On average you can expect to pay $1,605 for a flight from Westchester County to Chicago O'Hare Intl Airport. The cheapest flight overall is $148 while the most popular route, (White Plains Westchester County - Chicago O'Hare Intl) is currently priced at $255.

  • 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, August is the cheapest month in which you can book a flight from Westchester County to Chicago O'Hare Intl Airport (average of $245). Flying from Westchester County to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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
Beloit
Hoffman Estates
Skokie
Naperville
Des Plaines
Elgin
Arlington Heights
Racine
Rockford
Orland Park
Merrillville
Waukegan
Elk Grove Village
Downers Grove
Tinley Park
Evanston
Lake Geneva
Gurnee

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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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Elmira to Midway flights
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Stewart to Midway flights
Stewart to Rockford flights

Top 2 airlines flying from Westchester County to O'Hare Intl

Discover the top 2 airlines 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 August 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$96Average$421FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$334Average$459FlexibilityNo cancel feeOn-time71%

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