HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Westchester County

$169+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
avr. 21 — avr. 281
lun. 4/21
lun. 4/28
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 avril 16, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$320
(Delta)

One-way from

$169
(Delta)

Popular in

December

Cheapest in

September

Average price

$204
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
Search Deals
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. 8% potential increase in price ($17 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 April 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 avril 16, 2025.

This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 6/57:10 amORD - HPN
1 stop3h 48mDelta
mar. 6/105:15 pmHPN - ORD
1 stop15h 34mDelta
Deal found 4/16$320
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 6/54:15 pmMDW - HPN
1 stop4h 57mDelta
lun. 6/912:55 pmHPN - MDW
1 stop24h 34mDelta
Deal found 4/16$320
This American Airlines deal was found by Cheapflights users on 4/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/2312:49 pmORD - HPN
Nonstop2h 10mAmerican Airlines
mer. 8/274:30 pmHPN - ORD
Nonstop2h 38mAmerican Airlines
Deal found 4/16$349
This Mytrip deal was found by Cheapflights users on 4/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 6/62:19 pmORD - HPN
1 stop21h 11mMultiple Airlines
dim. 6/88:10 amHPN - ORD
2 stops36h 53mMultiple Airlines
Deal found 4/16$492

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 avril 16, 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

jeu. 6/5

7:10 am-11:58 am

1 stop3h 48m

White Plains Westchester County

mar. 6/10

5:15 pm-7:49 am

1 stop15h 34m

$320

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

jeu. 6/5

4:15 pm-10:12 pm

1 stop4h 57m

White Plains Westchester County

lun. 6/9

12:55 pm-12:29 pm

1 stop24h 34m

$320

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

sam. 8/23

12:49 pm-3:59 pm

Nonstop2h 10m

White Plains Westchester County

mer. 8/27

4:30 pm-6:08 pm

Nonstop2h 38m

$349

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

ven. 6/6

2:19 pm-12:30 pm

1 stop21h 11m

White Plains Westchester County

dim. 6/8

8:10 am-8:03 pm

2 stops36h 53m

$492

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

jeu. 4/24

9:55 am-3:49 pm

1 stop4h 54m

$169

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

jeu. 4/24

6:04 am-12:04 pm

1 stop5h 00m

$169

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

jeu. 5/15

12:49 pm-3:59 pm

Nonstop2h 10m

$201

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

mer. 8/6

11:28 am-11:25 am

1 stop22h 57m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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 $341). 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 avril 16, 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 avril 16, 2025.

The most flights from CHI to zzREU are scheduled on a Monday (6 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 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 avril 16, 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
7,916 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

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
7,916 reviews
Delta
8.0
Very good
7,916 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

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
7,916 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

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.

  • 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 (76%) or Envoy Air (76%) 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 $553, our data shows the cheapest flight currently is $200. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $308 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 $341). 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 LaGuardia flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Newark flights
Midway to Newark flights
Midway to John F Kennedy Intl flights
Midway to LaGuardia flights
St. Louis to LaGuardia flights
St. Louis to Newark flights
St. Louis to John F Kennedy Intl flights
O'Hare Intl to Buffalo flights
O'Hare Intl to Albany flights
O'Hare Intl to Syracuse flights
O'Hare Intl to Rochester flights
O'Hare Intl to White Plains flights
O'Hare Intl to Islip flights
Midway to White Plains flights
Midway to Rochester flights
Midway to Buffalo flights
St. Louis to Syracuse flights
Midway to Albany flights
Moline to LaGuardia flights
Moline to Newark flights
Peoria to LaGuardia flights
Midway to Syracuse flights
Moline to John F Kennedy Intl flights
Peoria to Newark flights
O'Hare Intl to Stewart flights
O'Hare Intl to Ithaca flights
St. Louis to White Plains flights
St. Louis to Albany flights
Evansville to Newark flights
St. Louis to Buffalo flights
Evansville to John F Kennedy Intl flights
O'Hare Intl to Binghamton flights
Midway to Ithaca flights
St. Louis to Rochester flights
Evansville to LaGuardia flights
Peoria to John F Kennedy Intl flights
Bloomington to LaGuardia flights
Midway to Binghamton flights
Bloomington to John F Kennedy Intl flights
Moline to Buffalo flights
Bloomington to Newark flights
St. Louis to Ithaca flights
O'Hare Intl to Elmira flights
Moline to Albany flights
Champaign to John F Kennedy Intl flights
Champaign to Newark flights
Peoria to Syracuse flights

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 avril 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$159Average$478FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$309Average$441FlexibilityNo 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.