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Westchester County

$74+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
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 November 20, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$189
(Kiwi.com)

One-way from

$74
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$213
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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Highest demand for flights based on searches. 5% potential increase in price ($11 potential increase over avg. RT price).
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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 November 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 November 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
Thu 12/47:40 amORD - HPN
1 stop26h 48mMultiple Airlines
Mon 12/812:10 pmHPN - ORD
2 stops10h 38mMultiple Airlines
Deal found 11/19$306
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Thu 12/117:40 amORD - HPN
1 stop26h 48mMultiple Airlines
Mon 12/158:00 amHPN - ORD
2 stops37h 01mMultiple Airlines
Deal found 11/18$318
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Thu 12/117:40 amORD - HPN
1 stop26h 48mMultiple Airlines
Tue 12/168:00 amHPN - ORD
2 stops37h 01mMultiple Airlines
Deal found 11/18$325
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/202:13 pmORD - HPN
Nonstop2h 13mAmerican Airlines
Sat 1/1712:00 pmHPN - ORD
Nonstop2h 45mAmerican Airlines
Deal found 11/19$349
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Sun 12/218:10 amORD - HPN
Nonstop2h 19mAmerican Airlines
Tue 12/305:56 pmHPN - ORD
Nonstop2h 47mAmerican Airlines
Deal found 11/19$380
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/202:13 pmORD - HPN
Nonstop2h 13mAmerican Airlines
Sun 12/285:16 pmHPN - ORD
1 stop4h 58mAmerican Airlines
Deal found 11/19$390
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/1012:09 pmORD - HPN
2 stops22h 20mMultiple Airlines
Fri 12/1212:10 pmHPN - ORD
1 stop9h 32mMultiple Airlines
Deal found 11/20$393
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 11/263:53 pmORD - HPN
2 stops42h 35mMultiple Airlines
Wed 12/31:14 pmHPN - ORD
1 stop24h 54mMultiple Airlines
Deal found 11/18$399
This American Airlines deal was found by Cheapflights users on 11/19. 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 stop6h 15mAmerican Airlines
Mon 12/293:00 pmHPN - ORD
1 stop5h 14mAmerican Airlines
Deal found 11/19$400
This Delta deal was found by Cheapflights users on 11/19. 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 11/276:00 amMDW - HPN
1 stop5h 00mDelta
Wed 12/312:55 pmHPN - MDW
1 stop6h 05mDelta
Deal found 11/19$419
This Delta deal was found by Cheapflights users on 11/18. 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 12/910:49 amMDW - HPN
1 stop10h 20mDelta
Tue 12/1612:45 pmHPN - MDW
1 stop4h 59mDelta
Deal found 11/18$426
This Delta deal was found by Cheapflights users on 11/19. 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.
Sun 12/219:29 amMDW - HPN
1 stop5h 20mDelta
Tue 12/3012:55 pmHPN - MDW
1 stop5h 31mDelta
Deal found 11/19$431

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 November 20, 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

MDW - HPN

MDWHPN

Chicago Midway

Tue 1/27

6:00 am-12:06 pm

1 stop5h 06m

White Plains Westchester County

Sat 1/31

5:15 pm-10:22 pm

1 stop6h 07m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sun 12/21

8:10 am-11:29 am

Nonstop2h 19m

White Plains Westchester County

Tue 12/30

4:30 pm-6:22 pm

Nonstop2h 52m

$380

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 1/27

7:05 am-2:26 pm

1 stop6h 21m

White Plains Westchester County

Sat 1/31

12:59 pm-9:49 am

2 stops21h 50m

$404

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 11/27

1:14 pm-10:09 pm

1 stop7h 55m

White Plains Westchester County

Tue 12/2

12:45 pm-6:43 pm

1 stop6h 58m

$419

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Mon 11/24

5:23 am-12:00 pm

1 stop5h 37m

White Plains Westchester County

Sat 12/6

12:55 pm-4:22 pm

1 stop4h 27m

$419

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Mon 11/24

5:23 am-12:00 pm

1 stop5h 37m

White Plains Westchester County

Tue 12/2

12:45 pm-6:43 pm

1 stop6h 58m

$419

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 11/27

5:23 am-12:00 pm

1 stop5h 37m

White Plains Westchester County

Wed 12/3

5:17 pm-8:35 pm

1 stop4h 18m

$419

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 11/27

6:45 am-11:59 am

1 stop4h 14m

White Plains Westchester County

Sat 12/6

12:55 pm-4:22 pm

1 stop4h 27m

$419

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 11/27

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Tue 12/2

4:29 pm-11:47 pm

1 stop8h 18m

$419

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 11/27

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Wed 12/3

12:55 pm-6:00 pm

1 stop6h 05m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 34 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 $209). 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 November 20, 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 6% on airfare.

Weekly flight availability from Chicago to Westchester County

Explore weekly flight availability from Chicago to Westchester County. 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 November 20, 2025.

The most flights from CHI to zzREU are scheduled on a Wednesday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

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 November 20, 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
8,002 reviews

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.3

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
8,002 reviews
Delta
7.9
Good
8,002 reviews

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.3

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
11,047 reviews
Delta
7.9
Good
8,002 reviews

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.3

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 $380, Delta can have you in Westchester County from Chicago in 2h 19m. 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 Qatar Airways (84%), Alaska Airlines (80%) or American Airlines (80%) 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 $510, 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 $232 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 $209). 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$374Average$465FlexibilityNo cancel feeOn-time71%

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