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O'Hare Intl

$129+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — ORD
oct. 31 — nov. 71
vie. 10/31
vie. 11/7
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 octubre 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$349
(American Airlines)

One-way from

$129
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$227
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
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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. 7% potential increase in price ($19 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 October 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 octubre 1, 2025.

This American Airlines deal was found by Cheapflights users on 9/29. 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.
mié. 10/295:57 pmHPN - ORD
Nonstop2h 41mAmerican Airlines
mié. 11/58:21 amORD - HPN
Nonstop2h 08mAmerican Airlines
Deal found 9/29$349
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
jue. 10/168:00 amHPN - ORD
2 stops16h 39mMultiple Airlines
dom. 10/192:41 pmORD - HPN
1 stop19h 47mMultiple Airlines
Deal found 9/29$366
This Kiwi.com deal was found by Cheapflights users on 10/1. 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.
mar. 10/2112:09 pmHPN - ORD
2 stops22h 59mMultiple Airlines
jue. 10/232:41 pmORD - HPN
1 stop19h 47mMultiple Airlines
Deal found 10/1$367
This Delta deal was found by Cheapflights users on 9/29. 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.
mié. 10/296:00 amHPN - ORD
1 stop5h 20mDelta
mié. 11/57:10 amORD - HPN
1 stop3h 49mDelta
Deal found 9/29$369
This Delta deal was found by Cheapflights users on 10/1. 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.
mié. 12/1712:55 pmHPN - ORD
1 stop22h 05mDelta
lun. 12/226:02 pmORD - HPN
1 stop20h 47mDelta
Deal found 10/1$379
This American Airlines deal was found by Cheapflights users on 9/29. 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.
sáb. 11/17:20 amHPN - ORD
Nonstop2h 36mAmerican Airlines
dom. 11/28:10 pmORD - HPN
Nonstop2h 19mAmerican Airlines
Deal found 9/29$380
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
mié. 10/151:14 pmHPN - ORD
2 stops21h 54mMultiple Airlines
dom. 10/192:41 pmORD - HPN
1 stop19h 47mMultiple Airlines
Deal found 9/30$382
This American Airlines deal was found by Cheapflights users on 9/29. 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.
mar. 10/285:57 pmHPN - ORD
Nonstop2h 41mAmerican Airlines
mié. 11/1212:48 pmORD - HPN
Nonstop2h 11mAmerican Airlines
Deal found 9/29$384
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
vie. 10/3112:10 pmHPN - ORD
1 stop12h 18mMultiple Airlines
dom. 11/21:50 pmORD - HPN
1 stop20h 38mMultiple Airlines
Deal found 9/29$385
This American Airlines deal was found by Cheapflights users on 9/29. 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.
mié. 11/266:00 amHPN - ORD
Nonstop2h 44mAmerican Airlines
sáb. 11/298:10 pmORD - HPN
Nonstop2h 19mAmerican Airlines
Deal found 9/29$389

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 octubre 1, 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

mié. 12/17

12:55 pm-10:00 am

1 stop22h 05m

Chicago O'Hare Intl

lun. 12/22

6:02 pm-3:49 pm

1 stop20h 47m

$379

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

sáb. 11/1

5:57 pm-7:38 pm

Nonstop2h 41m

Chicago O'Hare Intl

dom. 11/2

8:10 pm-11:29 pm

Nonstop2h 19m

$380

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

sáb. 11/8

12:45 pm-5:00 pm

1 stop5h 15m

Chicago O'Hare Intl

lun. 11/10

10:46 am-3:49 pm

1 stop4h 03m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

sáb. 11/1

6:00 am-10:20 am

1 stop5h 20m

Chicago O'Hare Intl

dom. 11/2

5:20 am-12:00 pm

1 stop5h 40m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

vie. 11/7

6:50 pm-11:58 pm

1 stop6h 08m

Chicago O'Hare Intl

dom. 11/9

5:23 am-12:00 pm

1 stop5h 37m

$431

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

jue. 11/27

12:45 pm-6:52 pm

1 stop7h 07m

Chicago O'Hare Intl

vie. 11/28

6:45 am-11:59 am

1 stop4h 14m

$431

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

vie. 12/12

5:17 pm-8:35 pm

1 stop4h 18m

Chicago O'Hare Intl

dom. 12/14

5:30 am-12:00 pm

1 stop5h 30m

$431

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

sáb. 10/11

5:20 pm-8:23 pm

1 stop4h 03m

Chicago O'Hare Intl

mar. 10/14

1:26 pm-10:09 pm

1 stop7h 43m

$439

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

mié. 12/17

5:59 pm-7:49 pm

Nonstop2h 50m

Chicago O'Hare Intl

sáb. 12/20

2:13 pm-5:26 pm

Nonstop2h 13m

$449

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

lun. 10/27

8:25 am-2:45 pm

2 stops31h 20m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/30

Showing 1-10 of 19 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 octubre 1, 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.

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 octubre 1, 2025.

The most flights from zzREU to ORD are scheduled on a Monday (8 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 octubre 1, 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
11,030 reviews

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Overall

7.2

Food

6.4

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
11,030 reviews
American Airlines
7.2
Good
11,030 reviews

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Overall

7.2

Food

6.4

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 and American Airlines can get you from Westchester County to Chicago O'Hare Intl Airport in just under 2h 41m. Your travel time can differ by up to 19h 24m. 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 Sun Country Air (100%), American Airlines (83%) and Envoy Air (83%).

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

    On average you can expect to pay $824 for a flight from Westchester County to Chicago O'Hare Intl Airport. The cheapest flight overall is $128 while the most popular route, (White Plains Westchester County - Chicago O'Hare Intl) is currently priced at $287.

  • 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
Skokie
Des Plaines
Gurnee
Hoffman Estates
Elgin
Racine
Rockford
Oak Brook
Elk Grove Village
Beloit
Downers Grove
Naperville
Orland Park
Merrillville
Bridgeview
Warrenville
Arlington Heights
Joliet

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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 octubre 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$349Average$473FlexibilityNo cancel feeOn-time71%

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