HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Westchester County

$200+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Westchester County with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 14, 2025.

Round-trip from

$307
(Delta)

One-way from

$200
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$218
From Chicago (CHI) to Westchester County
Search Deals
One-way flight from Chicago (CHI) to Westchester County
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. 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 9/67:15 amORD - HPN
1 stop7h 34mDelta
Tue 9/912:37 pmHPN - ORD
1 stop8h 46mDelta
Deal found 8/14$307
This Delta deal was found by Cheapflights users on 8/14. 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 9/67:15 amORD - HPN
1 stop7h 34mDelta
Mon 9/85:15 pmHPN - ORD
1 stop15h 49mDelta
Deal found 8/14$327
This Delta deal was found by Cheapflights users on 8/14. 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.
Fri 9/511:05 amORD - HPN
1 stop23h 52mDelta
Tue 9/912:37 pmHPN - ORD
1 stop8h 46mDelta
Deal found 8/14$337
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/138:15 amORD - HPN
Nonstop2h 14mAmerican Airlines
Tue 9/167:01 amHPN - ORD
Nonstop2h 32mAmerican Airlines
Deal found 8/14$349
This Delta deal was found by Cheapflights users on 8/14. 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 9/137:20 amORD - HPN
1 stop6h 09mDelta
Tue 9/165:20 pmHPN - ORD
1 stop4h 00mDelta
Deal found 8/14$369
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Tue 9/308:15 amORD - HPN
Nonstop2h 14mAmerican Airlines
Sun 10/56:00 amHPN - ORD
Nonstop2h 30mAmerican Airlines
Deal found 8/13$380
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Tue 9/912:49 pmORD - HPN
Nonstop2h 10mAmerican Airlines
Sat 9/137:01 amHPN - ORD
Nonstop2h 32mAmerican Airlines
Deal found 8/13$384
This Delta deal was found by Cheapflights users on 8/13. 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 8/307:15 amORD - HPN
1 stop3h 42mDelta
Sun 8/316:00 amHPN - ORD
1 stop7h 16mDelta
Deal found 8/13$404
This Delta deal was found by Cheapflights users on 8/13. 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 11/69:35 amMDW - HPN
1 stop5h 14mDelta
Sun 11/96:00 amHPN - MDW
1 stop6h 55mDelta
Deal found 8/13$431
This Delta deal was found by Cheapflights users on 8/13. 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 8/166:04 amMDW - HPN
1 stop4h 56mDelta
Wed 8/203:10 pmHPN - MDW
1 stop7h 34mDelta
Deal found 8/13$439
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 8/1510:31 amMDW - HPN
1 stop6h 31mDelta
Wed 8/203:10 pmHPN - MDW
1 stop7h 34mDelta
Deal found 8/13$511
This Delta deal was found by Cheapflights users on 8/13. 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 9/3010:35 amMDW - HPN
1 stop6h 25mDelta
Sun 10/56:00 amHPN - MDW
1 stop6h 48mDelta
Deal found 8/13$559

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 August 14, 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 9/6

7:15 am-3:49 pm

1 stop7h 34m

White Plains Westchester County

Tue 9/9

12:37 pm-8:23 pm

1 stop8h 46m

$307

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 9/6

7:15 am-3:49 pm

1 stop7h 34m

White Plains Westchester County

Mon 9/8

5:15 pm-8:04 am

1 stop15h 49m

$327

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 9/5

11:05 am-11:57 am

1 stop23h 52m

White Plains Westchester County

Tue 9/9

12:37 pm-8:23 pm

1 stop8h 46m

$337

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 10/1

8:15 am-11:29 am

Nonstop2h 14m

White Plains Westchester County

Sat 10/4

6:00 am-7:30 am

Nonstop2h 30m

$349

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 10/22

2:09 pm-5:27 pm

Nonstop2h 18m

White Plains Westchester County

Sat 10/25

5:57 pm-7:38 pm

Nonstop2h 41m

$349

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 9/13

8:15 am-11:29 am

Nonstop2h 14m

White Plains Westchester County

Tue 9/16

6:00 am-7:30 am

Nonstop2h 30m

$349

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 11/6

9:35 am-3:49 pm

1 stop5h 14m

White Plains Westchester County

Sun 11/9

6:00 am-11:55 am

1 stop6h 55m

$431

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 10/1

6:00 am-11:59 am

1 stop4h 59m

White Plains Westchester County

Sun 10/5

6:00 am-11:48 am

1 stop6h 48m

$559

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 9/30

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Sun 10/5

6:00 am-11:48 am

1 stop6h 48m

$559

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 10/16

9:35 am-3:49 pm

1 stop5h 14m

White Plains Westchester County

Sun 10/19

12:55 pm-6:25 pm

1 stop6h 30m

$589

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 33 results
1
2
3
4

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 August 14, 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 August 14, 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 August 14, 2025.
Peruse reviews from past customers who have flown with Delta, American Airlines, and Spirit 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
7,980 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

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
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

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
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

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!
Spirit Airlines
6.3
Okay
8,045 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

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.

  • 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 (80%), American Airlines (72%) or Envoy Air (72%) 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 $496, our data shows the cheapest flight currently is $263. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $359 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
Midway to LaGuardia flights
Midway to Newark flights
Midway to John F Kennedy Intl flights
St. Louis to Newark flights
St. Louis to LaGuardia flights
O'Hare Intl to Stewart flights
St. Louis to John F Kennedy Intl flights
O'Hare Intl to White Plains flights
O'Hare Intl to Albany flights
O'Hare Intl to Buffalo flights
O'Hare Intl to Rochester flights
O'Hare Intl to Syracuse flights
Midway to Albany flights
Midway to Buffalo flights
Midway to Syracuse flights
Midway to White Plains flights
St. Louis to Buffalo flights
St. Louis to Syracuse flights
Peoria to Newark flights
St. Louis to Albany flights
Peoria to LaGuardia flights
Moline to LaGuardia flights
Moline to Newark flights
Midway to Rochester flights
Evansville to John F Kennedy Intl flights
Moline to John F Kennedy Intl flights
O'Hare Intl to Islip flights
Peoria to Buffalo flights
Peoria to John F Kennedy Intl flights
Evansville to Newark flights
St. Louis to Rochester flights
O'Hare Intl to Ithaca flights
Evansville to LaGuardia flights
Champaign to Newark flights
Bloomington to John F Kennedy Intl flights
Champaign to John F Kennedy Intl flights
Bloomington to Newark flights
Moline to Albany flights
St. Louis to White Plains flights
Champaign to LaGuardia flights
Moline to Syracuse flights
Bloomington to Buffalo flights
Moline to Rochester flights
Midway to Ithaca flights
Bloomington to LaGuardia flights
Moline to Buffalo flights

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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$349Average$454FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.