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Westchester County

$118+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
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 septiembre 17, 2025.

Round-trip from

$248
(Kiwi.com)

One-way from

$118
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$187
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. 0% potential increase in price ($2 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 September 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 septiembre 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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. 11/52:47 pmORD - HPN
2 stops20h 52mMultiple Airlines
vie. 11/712:10 pmHPN - ORD
1 stop12h 18mMultiple Airlines
Deal found 9/15$248
This Kiwi.com deal was found by Cheapflights users on 9/16. 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. 11/112:47 pmORD - HPN
2 stops20h 47mMultiple Airlines
lun. 11/1712:10 pmHPN - ORD
1 stop12h 18mMultiple Airlines
Deal found 9/16$268
This Kiwi.com deal was found by Cheapflights users on 9/15. 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. 10/295:28 pmORD - HPN
2 stops17h 01mMultiple Airlines
vie. 10/3112:10 pmHPN - ORD
1 stop12h 18mMultiple Airlines
Deal found 9/15$274
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
lun. 9/295:17 pmORD - HPN
2 stops17h 12mMultiple Airlines
mié. 10/11:14 pmHPN - ORD
1 stop28h 37mMultiple Airlines
Deal found 9/15$288
This Kiwi.com deal was found by Cheapflights users on 9/17. 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. 10/211:36 amORD - HPN
1 stop22h 52mMultiple Airlines
lun. 10/68:25 amHPN - ORD
2 stops34h 28mMultiple Airlines
Deal found 9/17$294
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
dom. 11/91:50 pmORD - HPN
1 stop20h 38mMultiple Airlines
mié. 11/121:14 pmHPN - ORD
2 stops22h 27mMultiple Airlines
Deal found 9/15$301
This Kiwi.com deal was found by Cheapflights users on 9/16. 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. 10/162:41 pmORD - HPN
1 stop19h 47mMultiple Airlines
jue. 10/231:19 pmHPN - ORD
2 stops28h 54mMultiple Airlines
Deal found 9/16$330
This Delta deal was found by Cheapflights users on 9/17. 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.
jue. 11/276:45 amORD - HPN
2 stops14h 24mDelta
mar. 12/25:17 pmHPN - ORD
1 stop15h 47mDelta
Deal found 9/17$338
This American Airlines deal was found by Cheapflights users on 9/15. 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. 10/222:09 pmORD - HPN
Nonstop2h 18mAmerican Airlines
sáb. 10/255:57 pmHPN - ORD
Nonstop2h 41mAmerican Airlines
Deal found 9/15$349
This Delta deal was found by Cheapflights users on 9/15. 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.
lun. 11/175:08 pmORD - HPN
1 stop17h 59mDelta
mar. 11/253:08 pmHPN - ORD
1 stop7h 28mDelta
Deal found 9/15$351
This Delta deal was found by Cheapflights users on 9/15. 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.
mar. 11/188:55 amORD - HPN
2 stops12h 14mDelta
mar. 11/253:08 pmHPN - ORD
1 stop7h 28mDelta
Deal found 9/15$356
This Delta deal was found by Cheapflights users on 9/17. 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.
jue. 11/279:32 amMDW - HPN
2 stops11h 37mDelta
mar. 12/212:55 pmHPN - MDW
1 stop6h 05mDelta
Deal found 9/17$356

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 septiembre 17, 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

jue. 10/2

11:36 am-11:28 am

1 stop22h 52m

White Plains Westchester County

lun. 10/6

8:25 am-5:53 pm

2 stops34h 28m

$294

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

jue. 11/27

6:45 am-10:09 pm

2 stops14h 24m

White Plains Westchester County

mar. 12/2

5:17 pm-8:04 am

1 stop15h 47m

$338

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

mar. 11/18

8:55 am-10:09 pm

2 stops12h 14m

White Plains Westchester County

mar. 11/25

3:08 pm-9:36 pm

1 stop7h 28m

$356

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

mié. 10/22

9:42 am-6:00 pm

1 stop7h 18m

White Plains Westchester County

sáb. 10/25

5:20 pm-8:23 pm

1 stop4h 03m

$369

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

sáb. 11/22

9:41 am-4:34 pm

1 stop5h 53m

White Plains Westchester County

mar. 12/2

12:55 pm-6:00 pm

1 stop6h 05m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

mar. 11/18

6:45 am-3:49 pm

1 stop8h 04m

White Plains Westchester County

jue. 11/27

6:00 am-12:04 pm

1 stop7h 04m

$382

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

lun. 11/17

6:45 am-3:49 pm

1 stop8h 04m

White Plains Westchester County

lun. 11/24

6:41 pm-12:02 am

1 stop6h 21m

$382

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

mié. 11/19

6:45 am-3:49 pm

1 stop8h 04m

White Plains Westchester County

lun. 11/24

6:00 am-12:04 pm

1 stop7h 04m

$382

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

sáb. 10/18

7:10 am-3:49 pm

1 stop7h 39m

White Plains Westchester County

dom. 10/19

6:00 am-10:20 am

1 stop5h 20m

$385

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

mié. 11/19

6:45 am-10:09 pm

2 stops14h 24m

White Plains Westchester County

jue. 11/27

12:55 pm-4:36 pm

1 stop4h 41m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 39 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, January is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $276). Flying from Chicago to Westchester County in March is currently the most expensive (average of $338). 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 septiembre 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Westchester County as you normally would.

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 septiembre 17, 2025.

The most flights from CHI to zzREU are scheduled on a Monday (7 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 septiembre 17, 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
8.0
Very good
7,961 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

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
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

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
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

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 $338, Delta can have you in Westchester County from Chicago in 14h 24m. Airlines will cover a distance of 736 mi.

  • 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 (84%), Qatar Airways (78%) or American Airlines (77%) 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 $517, our data shows the cheapest flight currently is $144. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $248 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, January is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $276). Flying from Chicago to Westchester County in March is currently the most expensive (average of $338). 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 septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$358Average$459FlexibilityNo cancel feeOn-time71%

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