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Westchester County

$100+ Cheap flights from Chicago (CHI) to Westchester County

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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Chicago to Westchester County

Keep the following information in mind while searching for Chicago to Westchester County flight deals. Data was last updated October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$197
(Kiwi.com)

One-way from

$100
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$201
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
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From Chicago (CHI) to Westchester County
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One-way flight from Chicago (CHI) to Westchester County
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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($3 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 Chicago to Westchester County

Cheapest flights from Chicago to Westchester County
Explore the most affordable flight options available from Chicago to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/31:03 pmORD - HPN
2 stops22h 36mMultiple Airlines
Wed 12/101:14 pmHPN - ORD
1 stop24h 54mMultiple Airlines
Deal found 10/29$197
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/161:50 pmORD - HPN
1 stop20h 38mMultiple Airlines
Fri 11/218:00 amHPN - ORD
2 stops38h 57mMultiple Airlines
Deal found 10/28$337
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Sat 12/206:39 pmORD - HPN
Nonstop2h 20mAmerican Airlines
Sat 1/1712:00 pmHPN - ORD
Nonstop2h 45mAmerican Airlines
Deal found 10/29$349
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/161:50 pmORD - HPN
1 stop20h 38mMultiple Airlines
Sun 11/2312:09 pmHPN - ORD
2 stops30h 06mMultiple Airlines
Deal found 10/27$354
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/201:12 pmORD - HPN
1 stop4h 11mAmerican Airlines
Sat 1/33:00 pmHPN - ORD
1 stop7h 16mAmerican Airlines
Deal found 10/30$369
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Sat 12/206:39 pmORD - HPN
Nonstop2h 20mAmerican Airlines
Mon 12/295:56 pmHPN - ORD
Nonstop2h 47mAmerican Airlines
Deal found 10/29$380
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/307:00 amORD - HPN
1 stop3h 59mDelta
Thu 1/112:55 pmHPN - ORD
1 stop8h 41mDelta
Deal found 10/29$381
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Mon 11/175:15 amORD - HPN
2 stops29h 14mMultiple Airlines
Fri 11/2112:10 pmHPN - ORD
1 stop6h 20mMultiple Airlines
Deal found 10/29$382
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 12/258:00 amORD - HPN
1 stop5h 30mAmerican Airlines
Sat 12/273:00 pmHPN - ORD
1 stop7h 16mAmerican Airlines
Deal found 10/29$384
This Delta deal was found by Cheapflights users on 10/29. 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.
Sat 12/209:29 amMDW - HPN
1 stop5h 20mDelta
Sat 1/175:15 pmHPN - MDW
1 stop5h 54mDelta
Deal found 10/29$434
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/316:00 amMDW - HPN
1 stop5h 00mDelta
Thu 1/112:55 pmHPN - MDW
1 stop5h 31mDelta
Deal found 10/29$449
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/309:29 amMDW - HPN
1 stop5h 20mDelta
Fri 1/212:55 pmHPN - MDW
1 stop5h 31mDelta
Deal found 10/29$465

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Westchester County 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 October 30, 2025.
Use the filters below to find and compare flights from Chicago to Westchester County that are best for you.

Fly from

Chicago

Fly to

Westchester County

Route

Depart

Return

Price

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 12/20

1:12 pm-8:27 pm

1 stop6h 15m

White Plains Westchester County

Sat 1/17

10:00 am-3:17 pm

1 stop6h 17m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 4/4

9:30 am-4:40 pm

1 stop6h 10m

White Plains Westchester County

Tue 4/7

5:10 pm-8:38 pm

1 stop4h 28m

$369

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 4/1

9:20 am-4:40 pm

1 stop6h 20m

White Plains Westchester County

Sat 4/4

12:45 pm-6:34 pm

1 stop6h 49m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 12/30

7:00 am-11:59 am

1 stop3h 59m

White Plains Westchester County

Thu 1/1

12:55 pm-8:36 pm

1 stop8h 41m

$381

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 12/18

7:11 am-1:05 pm

1 stop4h 54m

White Plains Westchester County

Sat 12/27

5:16 pm-9:16 pm

1 stop5h 00m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 12/2

8:55 am-3:49 pm

1 stop5h 54m

White Plains Westchester County

Mon 12/8

5:17 pm-8:35 pm

1 stop4h 18m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 12/2

6:45 am-11:59 am

1 stop4h 14m

White Plains Westchester County

Sun 12/7

6:10 am-12:10 pm

1 stop7h 00m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 4/4

8:00 am-11:07 am

Nonstop2h 07m

White Plains Westchester County

Tue 4/7

4:25 pm-6:00 pm

Nonstop2h 35m

$419

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 12/12

9:45 am-4:46 pm

1 stop6h 01m

White Plains Westchester County

Sun 12/14

3:12 pm-7:31 pm

1 stop5h 19m

$431

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 12/5

1:20 pm-10:09 pm

1 stop7h 49m

White Plains Westchester County

Mon 12/8

12:55 pm-6:27 pm

1 stop6h 32m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 42 results
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Best time to book a flight from Chicago to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County from Chicago 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 Chicago to Westchester County

What is the cheapest month to book a flight from Chicago to Westchester County?

Currently, November is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $202). Flying from Chicago to Westchester County in September is currently the most expensive (average of $411). 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 CHI to REU?

Find hourly flight availability from Chicago to Westchester County. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

One of the essential ways to save on airfare from Chicago to Westchester County is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 7% on airfare.

Reviews of airlines servicing Westchester County

Get insights into the airlines that provide service to Westchester County. 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 Westchester County. Reviews last updated October 30, 2025.
Peruse reviews from past customers who have flown with Delta and American Airlines from Chicago to Westchester County to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Westchester County. 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 Chicago to Westchester County?

    For as low as $369, American Airlines can have you in Westchester County from Chicago in 6h 10m. Airlines will cover a distance of 736 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most reliable airlines from Chicago to Westchester County?

    No one likes to see their flight delayed. When booking a flight from Chicago to Westchester County consider choosing Alaska Airlines (88%), American Airlines (87%) or Envoy Air (87%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Westchester County?

    While on average a flight from Chicago to Westchester County is generally $470, our data shows the cheapest flight currently is $288. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $197 for that flight.

  • Can I find deals for flights from Chicago to Westchester County that include hotel bookings?

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

  • How can I find direct flights from Chicago to Westchester County?

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

  • Can I find deals for business class flights from Chicago to Westchester County?

    Yes. Cheapflights offers flight deals from Chicago to Westchester County 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 Chicago to Westchester County?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $202). Flying from Chicago to Westchester County in September is currently the most expensive (average of $411). 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

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Alternative routes for Chicago to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to Westchester County

Discover the top airline that operate flights from Chicago to Westchester County. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$373Average$464FlexibilityNo cancel feeOn-time71%

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