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Westchester County

$82+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Jan 4 — Jan 111
Sun 1/4
Sun 1/11
1 adult, Economy
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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 December 5, 2025.

This American Airlines deal was found by Cheapflights users on 12/3. 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 12/206:39 pmORD - HPN
Nonstop2h 20mAmerican Airlines
Sat 1/1712:00 pmHPN - ORD
Nonstop2h 45mAmerican Airlines
Deal found 12/3$399
This Kiwi.com deal was found by Cheapflights users on 12/3. 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.
Sun 12/72:36 pmORD - HPN
2 stops19h 52mMultiple Airlines
Wed 12/101:14 pmHPN - ORD
1 stop24h 54mMultiple Airlines
Deal found 12/3$411
This Kiwi.com deal was found by Cheapflights users on 12/4. 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.
Thu 12/117:40 amORD - HPN
1 stop26h 48mMultiple Airlines
Tue 12/168:00 amHPN - ORD
2 stops37h 01mMultiple Airlines
Deal found 12/4$420
This Kiwi.com deal was found by Cheapflights users on 12/3. 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.
Thu 12/117:40 amORD - HPN
1 stop26h 48mMultiple Airlines
Wed 12/171:14 pmHPN - ORD
2 stops22h 04mMultiple Airlines
Deal found 12/3$429
This American Airlines deal was found by Cheapflights users on 12/5. 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.
Fri 12/126:37 pmORD - HPN
Nonstop2h 22mAmerican Airlines
Sat 1/36:27 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Deal found 12/5$436
This American Airlines deal was found by Cheapflights users on 12/5. 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 12/206:39 pmORD - HPN
Nonstop2h 20mAmerican Airlines
Sun 1/115:15 pmHPN - ORD
1 stop6h 19mAmerican Airlines
Deal found 12/5$440
This Kiwi.com deal was found by Cheapflights users on 12/4. 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.
Thu 12/117:40 amORD - HPN
1 stop26h 48mMultiple Airlines
Thu 12/188:00 amHPN - ORD
2 stops28h 10mMultiple Airlines
Deal found 12/4$442
This American Airlines deal was found by Cheapflights users on 12/4. 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 12/308:00 amORD - HPN
1 stop5h 30mAmerican Airlines
Sat 1/35:16 pmHPN - ORD
1 stop5h 00mAmerican Airlines
Deal found 12/4$444
This Delta deal was found by Cheapflights users on 12/4. 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 12/109:59 amMDW - HPN
1 stop5h 38mDelta
Sat 12/1312:55 pmHPN - MDW
1 stop6h 11mDelta
Deal found 12/4$469
This Delta deal was found by Cheapflights users on 12/4. 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 12/169:34 amMDW - HPN
1 stop5h 15mDelta
Sat 1/312:55 pmHPN - MDW
1 stop5h 31mDelta
Deal found 12/4$484
This Delta deal was found by Cheapflights users on 12/5. 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 12/199:34 amMDW - HPN
1 stop5h 15mDelta
Sun 1/1112:38 pmHPN - MDW
1 stop5h 59mDelta
Deal found 12/5$487
This Delta deal was found by Cheapflights users on 12/4. 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 12/116:00 amMDW - HPN
1 stop5h 00mDelta
Tue 12/166:50 pmHPN - MDW
1 stop5h 57mDelta
Deal found 12/4$506

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 December 5, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$185
(Kiwi.com)

One-way from

$82
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$228
Provider with most accurate pricing for Chicago (CHI)-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-New York (NYC) flights.
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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. 5% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 5, 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

Wed 1/7

5:30 am-6:00 pm

1 stop11h 30m

White Plains Westchester County

Tue 1/13

4:29 pm-8:43 am

1 stop17h 14m

$317

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/28

7:05 am-10:00 pm

1 stop13h 55m

White Plains Westchester County

Tue 2/3

6:40 pm-10:05 am

1 stop16h 25m

$317

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/7

9:55 am-10:00 pm

1 stop11h 05m

White Plains Westchester County

Mon 1/12

6:40 pm-10:59 am

1 stop17h 19m

$317

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 1/10

5:30 am-6:00 pm

1 stop11h 30m

White Plains Westchester County

Tue 1/13

12:59 pm-11:59 pm

1 stop12h 00m

$318

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 1/10

5:30 am-10:00 pm

1 stop15h 30m

White Plains Westchester County

Wed 1/14

6:00 am-4:45 pm

1 stop11h 45m

$318

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/7

7:05 am-6:00 pm

1 stop9h 55m

White Plains Westchester County

Sat 1/10

6:00 am-7:35 pm

1 stop14h 35m

$318

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 1/24

7:05 am-10:00 pm

1 stop13h 55m

White Plains Westchester County

Tue 2/3

6:40 pm-10:05 am

1 stop16h 25m

$318

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/28

6:50 am-10:00 pm

2 stops14h 10m

White Plains Westchester County

Mon 2/2

6:40 pm-10:05 am

1 stop16h 25m

$322

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 1/10

6:50 am-10:00 pm

2 stops14h 10m

White Plains Westchester County

Mon 1/12

6:40 pm-10:59 am

1 stop17h 19m

$323

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/28

7:05 am-10:00 pm

1 stop13h 55m

White Plains Westchester County

Sat 1/31

6:00 am-4:38 pm

2 stops11h 38m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/5

Showing 1-10 of 40 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, August is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $226). Flying from Chicago to Westchester County in September is currently the most expensive (average of $411). 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 December 5, 2025.

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 at noon could potentially save you up to 6% on airfare.

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 December 5, 2025.

The most flights from CHI to zzREU are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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 December 5, 2025.
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.
American Airlines
7.2
Good
11,043 reviews

Food

6.5

Crew

8.0

Comfort

7.2

Boarding

7.5

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Adwitiya,Sep 2025

DEL - JFK

I recently flew AA’s business class from Delhi to New York, and while the experience ticked the basic boxes, it didn’t quite soar. - Dining: I opted for the vegetarian meal, which was… fine. Not memorable, not offensive—just hovering in the realm of “meh.” The menu could use a refresh with more thoughtful, flavorful options. - Seating: AA seems to be chasing quantity over quality, squeezing in as many business class seats as possible. Yes, they’re lie-flat, but noticeably narrower than what you’d find on other international carriers. Comfort was passable, but not premium. Overall, I’d call it “business class lite.” It gets the job done, but lacks the finesse and attention to detail that elevate a journey. A few strategic tweaks—better food, more spacious seating, and a touch more hospitality—could make a world of difference.
American Airlines
7.2
Good
11,043 reviews
American Airlines
7.2
Good
11,043 reviews

Food

6.5

Crew

8.0

Comfort

7.2

Boarding

7.5

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Adwitiya,Sep 2025

DEL - JFK

I recently flew AA’s business class from Delhi to New York, and while the experience ticked the basic boxes, it didn’t quite soar. - Dining: I opted for the vegetarian meal, which was… fine. Not memorable, not offensive—just hovering in the realm of “meh.” The menu could use a refresh with more thoughtful, flavorful options. - Seating: AA seems to be chasing quantity over quality, squeezing in as many business class seats as possible. Yes, they’re lie-flat, but noticeably narrower than what you’d find on other international carriers. Comfort was passable, but not premium. Overall, I’d call it “business class lite.” It gets the job done, but lacks the finesse and attention to detail that elevate a journey. A few strategic tweaks—better food, more spacious seating, and a touch more hospitality—could make a world of difference.

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 $317, Delta can have you in Westchester County from Chicago in 11h 30m. 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 American Airlines (79%), Envoy Air (79%) or Qatar Airways (75%) 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 $465, our data shows the cheapest flight currently is $361. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $318 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, August is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $226). Flying from Chicago to Westchester County in September is currently the most expensive (average of $411). 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 December 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$375Average$470FlexibilityNo cancel feeOn-time71%

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