Westchester County

$139+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Jul 3 — Jul 101
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Cheap 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 3, 2026.

This American Airlines deal was found by Cheapflights users on 6/1. 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 8/156:35 pm
ORD
-
HPN
Nonstop2h 24m
American Airlines
Sat 8/227:12 am
HPN
-
ORD
Nonstop2h 40m
American Airlines
Deal found 6/1$395
This Delta deal was found by Cheapflights users on 5/31. 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 7/217:17 pm
ORD
-
HPN
1 stop15h 39m
Delta
Sat 7/256:49 pm
HPN
-
ORD
1 stop6h 04m
Delta
Deal found 5/31$414
This Delta deal was found by Cheapflights users on 5/31. 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 7/216:58 pm
MDW
-
HPN
1 stop15h 58m
Delta
Sat 7/2512:36 pm
HPN
-
MDW
1 stop6h 31m
Delta
Deal found 5/31$414
This Delta deal was found by Cheapflights users on 6/1. 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 8/156:51 am
ORD
-
HPN
1 stop4h 05m
Delta
Sat 8/2212:36 pm
HPN
-
ORD
1 stop4h 41m
Delta
Deal found 6/1$415
This Delta deal was found by Cheapflights users on 5/31. 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.
Wed 8/56:05 am
MDW
-
HPN
1 stop4h 58m
Delta
Sat 8/812:36 pm
HPN
-
MDW
1 stop6h 57m
Delta
Deal found 5/31$415
This American Airlines deal was found by Cheapflights users on 5/30. 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 6/137:29 pm
ORD
-
HPN
Nonstop2h 22m
American Airlines
Sat 7/114:30 pm
HPN
-
ORD
Nonstop2h 50m
American Airlines
Deal found 5/30$425
This American Airlines deal was found by Cheapflights users on 6/1. 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 8/126:35 pm
ORD
-
HPN
Nonstop2h 24m
American Airlines
Thu 8/204:30 pm
HPN
-
ORD
Nonstop2h 49m
American Airlines
Deal found 6/1$439
This Delta deal was found by Cheapflights users on 6/1. 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 6/277:01 am
ORD
-
HPN
1 stop3h 57m
Delta
Mon 6/295:10 pm
HPN
-
ORD
1 stop20h 54m
Delta
Deal found 6/1$444
This American Airlines deal was found by Cheapflights users on 6/2. 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 6/107:37 pm
ORD
-
HPN
Nonstop2h 22m
American Airlines
Sat 6/135:59 pm
HPN
-
ORD
Nonstop2h 54m
American Airlines
Deal found 6/2$455
This Delta deal was found by Cheapflights users on 5/31. 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 7/217:17 pm
ORD
-
HPN
1 stop15h 39m
Delta
Sun 7/266:00 am
HPN
-
ORD
1 stop5h 10m
Delta
Deal found 5/31$458
This Delta deal was found by Cheapflights users on 6/1. 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 12/129:55 am
MDW
-
HPN
1 stop5h 46m
Delta
Sun 12/1312:45 pm
HPN
-
MDW
1 stop6h 52m
Delta
Deal found 6/1$459
This Delta deal was found by Cheapflights users on 6/2. 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.
Wed 6/106:00 am
MDW
-
HPN
1 stop5h 09m
Delta
Sat 6/1312:38 pm
HPN
-
MDW
1 stop6h 33m
Delta
Deal found 6/2$475

Find 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 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$395
(American Airlines)

One-way from

$139
(Kiwi.com)

Popular in

May

Cheapest in

January

Average price

$252
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
From Chicago (CHI) to Westchester County
One-way flight from Chicago (CHI) to Westchester County
Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Average for round-trip flights in June 2026

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 3, 2026.
Use the filters below to find and compare flights from Chicago to Westchester County that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 7/1

6:00 am-12:14 pm

1 stop5h 14m

White Plains Westchester County

Wed 7/8

10:29 am-4:15 pm

1 stop6h 46m

$415

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 7/22

7:05 am-3:47 pm

1 stop7h 42m

White Plains Westchester County

Thu 7/30

6:49 pm-11:53 pm

1 stop6h 04m

$458

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 7/21

3:22 pm-10:25 pm

1 stop6h 03m

White Plains Westchester County

Thu 7/30

6:49 pm-11:53 pm

1 stop6h 04m

$459

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 7/8

9:19 am-3:47 pm

1 stop5h 28m

White Plains Westchester County

Mon 7/13

4:29 pm-10:15 pm

1 stop6h 46m

$459

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 8/13

9:24 am-3:48 pm

1 stop5h 24m

White Plains Westchester County

Sun 8/16

6:00 am-9:59 am

1 stop4h 59m

$503

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 7/2

9:17 am-3:49 pm

1 stop5h 32m

White Plains Westchester County

Thu 7/9

10:29 am-4:15 pm

1 stop6h 46m

$503

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 6/6

5:30 am-12:02 pm

1 stop5h 32m

White Plains Westchester County

Sun 6/7

12:38 pm-6:29 pm

1 stop6h 51m

$519

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 7/3

9:54 am-4:30 pm

1 stop5h 36m

White Plains Westchester County

Mon 7/6

12:38 pm-6:31 pm

1 stop6h 53m

$531

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 9/25

9:30 am-3:45 pm

1 stop5h 15m

White Plains Westchester County

Sun 9/27

10:29 am-4:11 pm

1 stop6h 42m

$531

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Mon 6/29

9:54 am-4:30 pm

1 stop5h 36m

White Plains Westchester County

Thu 7/9

12:36 pm-6:25 pm

1 stop6h 49m

$533

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/2

Showing 1-10 of 42 resultsSorted by cheapest first
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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, March is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $124). Flying from Chicago to Westchester County in February is currently the most expensive (average of $415). 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 3, 2026.

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 afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 4% on airfare.

What is the cheapest day to fly from Chicago to Westchester County?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Westchester County. Price data was last updated on May 30, 2026.

Travelers seeking maximum savings on their Chicago to Westchester County flight should consider departing on Saturday afternoons when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 3, 2026.
Peruse reviews from past customers who have flown with 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.

Comfort

7.2

Overall

7.1

Boarding

7.5

Entertainment

6.9

Crew

7.9

Food

6.4

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

Comfort

7.2

Overall

7.1

Boarding

7.5

Entertainment

6.9

Crew

7.9

Food

6.4

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

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 $458, Delta can have you in Westchester County from Chicago in 7h 42m. 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 Qatar Airways (83%), Alaska Airlines (82%) or American Airlines (71%) 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 $489, our data shows the cheapest flight currently is $285. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $415 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, March is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $124). Flying from Chicago to Westchester County in February is currently the most expensive (average of $415). 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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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 June 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$380Average$491FlexibilityNo cancel feeOn-time71%

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