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O'Hare Intl

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

HPN — ORD
Sep 2 — Sep 91
Wed 9/2
Wed 9/9
1 adult, Economy
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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 August 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$396
(lol.travel)

One-way from

$139
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$292
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. 17% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 2026
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Cheapflights Insights

Everything you need to know about your flight from Westchester County to Chicago O'Hare Intl Airport

How far ahead should I book a flight from Westchester County to Chicago O'Hare Intl Airport?

The price you pay for your flight from Westchester County to Chicago O'Hare Intl Airport may vary depending on when you book. For the best chance of a lower fare, look to book 33 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 $449). Flying from Westchester County to Chicago O'Hare Intl Airport in May is currently the most expensive (average of $543). 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 3, 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.

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 3, 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
11,844 reviews

Crew

7.9

Food

6.4

Comfort

7.2

Entertainment

6.8

Overall

7.1

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
11,844 reviews
American Airlines
7.1
Good
11,844 reviews

Crew

7.9

Food

6.4

Comfort

7.2

Entertainment

6.8

Overall

7.1

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 and JetBlue can get you from Westchester County to Chicago O'Hare Intl Airport in just under 4h 52m. Your travel time can differ by up to 6h 52m. 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 Qatar Airways (78%), American Airlines (77%) and Envoy Air (77%).

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

    On average you can expect to pay $798 for a flight from Westchester County to Chicago O'Hare Intl Airport. The cheapest flight overall is $235 while the most popular route, (White Plains Westchester County - Chicago O'Hare Intl) is currently priced at $294.

  • 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 $449). Flying from Westchester County to Chicago O'Hare Intl Airport in May is currently the most expensive (average of $543). 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
Benton Harbor
Rosemont
Schaumburg
Naperville
Lake Geneva
Oak Brook
Oakbrook Terrace
Delavan
Gurnee
South Holland
Libertyville
Orland Park
Hoffman Estates
Beloit
Rockford
Aurora
Racine
Great Lakes
Janesville
Joliet

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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 August 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$383Average$523FlexibilityNo cancel feeOn-time71%

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