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Westchester County

$99+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HPN
Mar 18 — Mar 251
Wed 3/18
Wed 3/25
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 February 16, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/15. 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 5/71:12 pm
ORD
-
HPN
1 stop6h 47m
Multiple Airlines
Sun 5/108:00 am
HPN
-
ORD
1 stop16h 16m
Multiple Airlines
Deal found 2/15$293
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Wed 3/258:14 am
ORD
-
HPN
Nonstop2h 15m
American Airlines
Sat 3/284:30 pm
HPN
-
ORD
Nonstop2h 48m
American Airlines
Deal found 2/13$355
This Delta deal was found by Cheapflights users on 2/15. 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 3/1011:10 am
ORD
-
HPN
1 stop9h 57m
Delta
Fri 3/206:59 pm
HPN
-
ORD
1 stop14h 31m
Delta
Deal found 2/15$370
This Delta deal was found by Cheapflights users on 2/13. 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.
Wed 3/257:10 am
ORD
-
HPN
1 stop3h 43m
Delta
Sat 3/2812:35 pm
HPN
-
ORD
1 stop4h 43m
Delta
Deal found 2/13$375
This Delta deal was found by Cheapflights users on 2/15. 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 3/176:00 am
MDW
-
HPN
1 stop5h 03m
Delta
Tue 3/2412:48 pm
HPN
-
MDW
1 stop5h 34m
Delta
Deal found 2/15$375
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Sat 2/288:15 am
ORD
-
HPN
2 stops26h 13m
Multiple Airlines
Mon 3/212:08 pm
HPN
-
ORD
1 stop12h 29m
Multiple Airlines
Deal found 2/15$378
This Delta deal was found by Cheapflights users on 2/15. 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.
Mon 3/95:30 am
ORD
-
HPN
1 stop15h 37m
Delta
Fri 3/206:59 pm
HPN
-
ORD
1 stop14h 31m
Delta
Deal found 2/15$383
This American Airlines deal was found by Cheapflights users on 2/15. 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 3/118:14 am
ORD
-
HPN
Nonstop2h 15m
American Airlines
Wed 3/1812:00 pm
HPN
-
ORD
Nonstop2h 43m
American Airlines
Deal found 2/15$385
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Thu 3/266:38 pm
ORD
-
HPN
Nonstop2h 21m
American Airlines
Wed 4/15:29 pm
HPN
-
ORD
Nonstop2h 48m
American Airlines
Deal found 2/13$389
This Delta deal was found by Cheapflights users on 2/15. 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 3/107:59 pm
ORD
-
HPN
1 stop12h 45m
Delta
Sat 3/146:00 am
HPN
-
ORD
1 stop15h 02m
Delta
Deal found 2/15$390
This Delta deal was found by Cheapflights users on 2/12. 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 6/249:30 am
MDW
-
HPN
1 stop6h 03m
Delta
Sat 6/2712:45 pm
HPN
-
MDW
1 stop6h 46m
Delta
Deal found 2/12$405
This Delta deal was found by Cheapflights users on 2/15. 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 6/56:30 am
MDW
-
HPN
1 stop6h 59m
Delta
Tue 6/912:45 pm
HPN
-
MDW
1 stop6h 46m
Delta
Deal found 2/15$409

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 February 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$355
(American Airlines)

One-way from

$99
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$221
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. 5% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 16, 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

Tue 3/17

6:38 pm-9:59 pm

Nonstop2h 21m

White Plains Westchester County

Tue 3/24

6:30 am-8:20 am

Nonstop2h 50m

$355

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 3/25

1:38 pm-4:47 pm

Nonstop2h 09m

White Plains Westchester County

Sat 3/28

4:30 pm-6:18 pm

Nonstop2h 48m

$355

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 3/11

7:10 am-6:18 pm

1 stop10h 08m

White Plains Westchester County

Fri 3/20

6:59 pm-8:30 am

1 stop14h 31m

$370

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 3/14

9:50 am-10:07 pm

1 stop11h 17m

White Plains Westchester County

Fri 3/20

6:59 pm-8:30 am

1 stop14h 31m

$370

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 6/24

10:35 am-4:33 pm

1 stop4h 58m

White Plains Westchester County

Sat 6/27

12:45 pm-4:36 pm

1 stop4h 51m

$375

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 3/25

7:10 am-11:53 am

1 stop3h 43m

White Plains Westchester County

Sat 3/28

12:35 pm-4:18 pm

1 stop4h 43m

$375

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 3/17

6:00 am-12:03 pm

1 stop5h 03m

White Plains Westchester County

Tue 3/24

12:48 pm-5:22 pm

1 stop5h 34m

$375

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 6/24

9:30 am-4:33 pm

1 stop6h 03m

White Plains Westchester County

Sat 6/27

12:45 pm-6:31 pm

1 stop6h 46m

$405

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 6/5

6:30 am-2:29 pm

1 stop6h 59m

White Plains Westchester County

Tue 6/9

12:45 pm-6:31 pm

1 stop6h 46m

$409

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 3/3

6:00 am-2:28 pm

1 stop7h 28m

White Plains Westchester County

Sat 3/7

5:12 pm-10:31 pm

1 stop6h 19m

$435

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/14

Showing 1-10 of 33 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 $148). Flying from Chicago to Westchester County in February is currently the most expensive (average of $456). 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 February 16, 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 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 February 7, 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 February 16, 2026.

The most flights from CHI to zzREU are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, 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 February 16, 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
11,294 reviews

Boarding

7.5

Overall

7.2

Food

6.4

Comfort

7.2

Crew

8.0

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
11,294 reviews
American Airlines
7.2
Good
11,294 reviews

Boarding

7.5

Overall

7.2

Food

6.4

Comfort

7.2

Crew

8.0

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 $355, American Airlines can have you in Westchester County from Chicago in 2h 21m. Airlines will cover a distance of 736 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 (73%), American Airlines (64%) or Envoy Air (64%) 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 $433, our data shows the cheapest flight currently is $289. When looking at the most popular route, (Chicago O'Hare Intl - White Plains Westchester County), you can expect to pay $293 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 $148). Flying from Chicago to Westchester County in February is currently the most expensive (average of $456). 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 February 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$375Average$481FlexibilityNo cancel feeOn-time71%

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