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Westchester County

$81+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
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 January 6, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$265
(Kiwi.com)

One-way from

$81
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$148
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
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One-way flight from Chicago (CHI) to Westchester County
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Highest demand for flights based on searches. 6% potential increase in price ($15 potential increase over avg. RT price).
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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 January 2026
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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 January 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/4. 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.
Mon 2/169:41 pmORD - HPN
2 stops12h 47mMultiple Airlines
Mon 2/2312:08 pmHPN - ORD
1 stop12h 29mMultiple Airlines
Deal found 1/4$265
This American Airlines deal was found by Cheapflights users on 1/6. 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 1/2810:05 amORD - HPN
1 stop11h 54mAmerican Airlines
Tue 2/107:00 amHPN - ORD
1 stop12h 10mAmerican Airlines
Deal found 1/6$285
This Kiwi.com deal was found by Cheapflights users on 1/4. 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 4/92:00 pmORD - HPN
1 stop20h 28mMultiple Airlines
Mon 4/1312:08 pmHPN - ORD
2 stops29h 39mMultiple Airlines
Deal found 1/4$327
This American Airlines deal was found by Cheapflights users on 1/4. 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.
Sat 3/286:38 pmORD - HPN
Nonstop2h 21mAmerican Airlines
Wed 4/15:29 pmHPN - ORD
Nonstop2h 48mAmerican Airlines
Deal found 1/4$349
This Delta deal was found by Cheapflights users on 1/6. 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 1/2711:15 amORD - HPN
1 stop9h 45mDelta
Sat 2/75:15 pmHPN - ORD
1 stop7h 41mDelta
Deal found 1/6$356
This Delta deal was found by Cheapflights users on 1/6. 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 1/275:30 amORD - HPN
1 stop11h 30mDelta
Mon 2/96:40 pmHPN - ORD
1 stop15h 02mDelta
Deal found 1/6$357
This Delta deal was found by Cheapflights users on 1/6. 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 1/315:30 amORD - HPN
1 stop5h 36mDelta
Wed 2/1112:38 pmHPN - ORD
1 stop9h 27mDelta
Deal found 1/6$367
This Delta deal was found by Cheapflights users on 1/4. 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.
Sat 3/287:10 amORD - HPN
1 stop3h 33mDelta
Wed 4/13:13 pmHPN - ORD
1 stop5h 36mDelta
Deal found 1/4$369
This Delta deal was found by Cheapflights users on 1/5. 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.
Sat 3/149:35 amORD - HPN
1 stop6h 00mDelta
Mon 3/165:17 pmHPN - ORD
1 stop21h 00mDelta
Deal found 1/5$376
This Delta deal was found by Cheapflights users on 1/5. 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.
Tue 3/310:49 amMDW - HPN
1 stop6h 11mDelta
Thu 3/2612:48 pmHPN - MDW
1 stop5h 07mDelta
Deal found 1/5$400
This Delta deal was found by Cheapflights users on 1/4. 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.
Sat 1/175:31 pmMDW - HPN
1 stop15h 17mDelta
Wed 2/254:29 pmHPN - MDW
1 stop7h 02mDelta
Deal found 1/4$401
This Delta deal was found by Cheapflights users on 1/6. 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 1/76:45 amMDW - HPN
1 stop6h 41mDelta
Wed 1/144:29 pmHPN - MDW
1 stop6h 38mDelta
Deal found 1/6$415

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 January 6, 2026.
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 1/29

9:55 am-10:00 pm

1 stop11h 05m

White Plains Westchester County

Wed 2/11

5:12 pm-9:05 pm

1 stop4h 53m

$356

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 1/27

9:55 am-10:00 pm

1 stop11h 05m

White Plains Westchester County

Wed 2/11

12:38 pm-4:57 pm

1 stop5h 19m

$356

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 1/27

5:30 am-6:00 pm

1 stop11h 30m

White Plains Westchester County

Mon 2/9

6:40 pm-8:42 am

1 stop15h 02m

$357

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 1/29

9:55 am-10:00 pm

1 stop11h 05m

White Plains Westchester County

Mon 2/9

12:59 pm-9:00 pm

1 stop9h 01m

$357

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 3/28

7:10 am-11:43 am

1 stop3h 33m

White Plains Westchester County

Wed 4/1

3:13 pm-7:49 pm

1 stop5h 36m

$369

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 1/31

6:50 am-11:56 am

1 stop4h 06m

White Plains Westchester County

Sat 2/7

12:38 pm-4:38 pm

1 stop5h 00m

$385

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 1/28

5:30 am-6:00 pm

1 stop11h 30m

White Plains Westchester County

Fri 2/13

12:36 pm-4:41 pm

1 stop5h 05m

$390

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 1/29

9:55 am-10:00 pm

1 stop11h 05m

White Plains Westchester County

Sun 2/8

12:38 pm-4:28 pm

1 stop4h 50m

$390

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 3/4

5:25 am-12:06 pm

1 stop5h 41m

White Plains Westchester County

Thu 3/26

3:13 pm-7:49 pm

1 stop5h 36m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 3/21

7:10 am-11:43 am

1 stop3h 33m

White Plains Westchester County

Sun 3/22

5:17 pm-8:14 pm

1 stop3h 57m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 43 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, March is the cheapest month in which you can book a flight from Chicago to Westchester County (average of $135). Flying from Chicago to Westchester County in November is currently the most expensive (average of $416). 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 January 6, 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 evening tend to be the most expensive. A flight in the morning could potentially save you up to 5% 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 January 3, 2026.

Travelers seeking maximum savings on their Chicago to Westchester County flight should consider departing on Sunday at noon 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.

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 January 6, 2026.

The most flights from CHI to zzREU are scheduled on a Monday (6 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (3 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 January 6, 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.
American Airlines
7.2
Good
11,083 reviews

Entertainment

6.9

Overall

7.2

Food

6.4

Crew

8.0

Comfort

7.2

Boarding

7.5

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
11,083 reviews
American Airlines
7.2
Good
11,083 reviews

Entertainment

6.9

Overall

7.2

Food

6.4

Crew

8.0

Comfort

7.2

Boarding

7.5

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 $356, Delta can have you in Westchester County from Chicago in 11h 05m. 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 Alaska Airlines (74%), American Airlines (68%) or Envoy Air (68%) 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 $245. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $327 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 $135). Flying from Chicago to Westchester County in November is currently the most expensive (average of $416). 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.

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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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$375Average$476FlexibilityNo cancel feeOn-time71%

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