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Westchester County

$201+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$328
(Delta)

One-way from

$201
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$233
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. 7% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/12. 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 8/287:15 amORD - HPN
1 stop7h 34mDelta
Tue 9/25:15 pmHPN - ORD
1 stop15h 49mDelta
Deal found 6/12$328
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 10/228:14 amORD - HPN
Nonstop2h 10mAmerican Airlines
Sat 10/2512:00 pmHPN - ORD
Nonstop2h 36mAmerican Airlines
Deal found 6/11$349
This Delta deal was found by Cheapflights users on 6/9. 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 7/19:24 amMDW - HPN
1 stop5h 21mDelta
Sat 7/512:55 pmHPN - MDW
1 stop6h 46mDelta
Deal found 6/9$369
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/33:29 pmORD - HPN
2 stops20h 10mMultiple Airlines
Sun 9/71:19 pmHPN - ORD
2 stops30h 58mMultiple Airlines
Deal found 6/10$453

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 June 12, 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

Thu 8/28

7:15 am-3:49 pm

1 stop7h 34m

White Plains Westchester County

Tue 9/2

5:15 pm-8:04 am

1 stop15h 49m

$328

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 7/16

8:20 am-11:29 am

Nonstop2h 09m

White Plains Westchester County

Sat 7/19

7:26 am-8:58 am

Nonstop2h 32m

$349

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 7/1

9:24 am-3:45 pm

1 stop5h 21m

White Plains Westchester County

Sat 7/5

12:55 pm-6:41 pm

1 stop6h 46m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 9/3

3:29 pm-12:39 pm

2 stops20h 10m

White Plains Westchester County

Sun 9/7

1:19 pm-7:17 pm

2 stops30h 58m

$453

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 6/28

8:19 am-12:30 pm

1 stop27h 11m

$201

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 8/21

12:19 pm-11:25 pm

2 stops10h 06m

$205

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Mon 8/25

7:15 am-3:49 pm

1 stop7h 34m

$252

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 7/9

9:25 am-3:43 pm

1 stop5h 18m

$256

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 7/18

10:31 am-4:51 pm

3 stops29h 20m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 $339). 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 June 12, 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 June 12, 2025.

The most flights from CHI to zzREU are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 June 12, 2025.
Read through reviews of airlines operating flights from Chicago to Westchester County, such as Delta and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,946 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

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
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

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
7,946 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

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.

  • 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 (80%), American Airlines (78%) or Envoy Air (78%) 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 $527, our data shows the cheapest flight currently is $174. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $389 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 $339). 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 2 airlines flying from Chicago to Westchester County

Discover the top 2 airlines 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$159Average$306FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$309Average$427FlexibilityNo cancel feeOn-time71%

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