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Westchester County

$79+ Cheap flights from Illinois 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.
ORD — HPN
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Illinois to Westchester County

Cheapest flights from Illinois to Westchester County
Explore the most affordable flight options available from Illinois to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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.
Tue 12/306:02 amSTL - HPN
1 stop7h 28mAmerican Airlines
Fri 1/26:27 amHPN - STL
1 stop8h 09mAmerican Airlines
Deal found 12/16$383
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/316:00 amSTL - HPN
1 stop4h 29mAmerican Airlines
Sun 1/46:56 pmHPN - STL
1 stop5h 59mAmerican Airlines
Deal found 12/16$388
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/208:10 amORD - HPN
Nonstop2h 19mAmerican Airlines
Sat 1/1712:00 pmHPN - ORD
Nonstop2h 45mAmerican Airlines
Deal found 12/17$399
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/2412:50 pmORD - HPN
Nonstop2h 09mAmerican Airlines
Fri 12/266:29 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Deal found 12/16$436
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/301:14 pmORD - HPN
1 stop22h 20mMultiple Airlines
Sun 1/412:09 pmHPN - ORD
2 stops45h 22mMultiple Airlines
Deal found 12/17$440
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/172:12 pmORD - HPN
Nonstop2h 17mAmerican Airlines
Tue 12/236:29 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Deal found 12/16$449
This Delta deal was found by Cheapflights users on 12/17. 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 12/251:22 pmORD - HPN
1 stop7h 47mDelta
Fri 1/26:55 pmHPN - ORD
1 stop6h 07mDelta
Deal found 12/17$456
This Delta deal was found by Cheapflights users on 12/15. 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.
Sat 12/209:29 amMDW - HPN
1 stop5h 20mDelta
Sat 1/176:00 amHPN - MDW
1 stop5h 32mDelta
Deal found 12/15$456
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/179:40 amORD - HPN
1 stop6h 06mAmerican Airlines
Wed 12/2412:00 pmHPN - ORD
Nonstop2h 43mAmerican Airlines
Deal found 12/16$459
This Delta deal was found by Cheapflights users on 12/17. 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 12/251:22 pmORD - HPN
1 stop7h 47mDelta
Thu 1/16:03 amHPN - ORD
1 stop14h 35mDelta
Deal found 12/17$467
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/301:14 pmORD - HPN
1 stop22h 20mMultiple Airlines
Fri 1/212:10 pmHPN - ORD
2 stops25h 57mMultiple Airlines
Deal found 12/17$473
This Delta deal was found by Cheapflights users on 12/17. 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 12/244:04 pmBMI - HPN
1 stop5h 05mDelta
Mon 12/294:29 pmHPN - BMI
1 stop6h 42mDelta
Deal found 12/17$509

Find flight deals from Illinois to Westchester County

Keep the following information in mind while searching for Illinois to Westchester County flight deals. Data was last updated December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$261
(Delta)

One-way from

$79
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$232
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.
Search Deals
From Illinois to Westchester County
Search Deals
One-way flight from Illinois to Westchester County
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 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 Illinois 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 18, 2025.
Use the filters below to find and compare flights from Illinois to Westchester County that are best for you.

Fly from

Illinois

Fly to

Westchester County

Route

Depart

Return

Price

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 1/9

5:35 am-11:28 am

1 stop4h 53m

White Plains Westchester County

Tue 1/13

12:08 pm-1:13 pm

2 stops26h 05m

$244

St. LouisWhite Plains

STL - HPN

STLHPN

Lambert-St Louis

Tue 1/20

6:35 am-11:56 am

1 stop4h 21m

White Plains Westchester County

Tue 1/20

5:12 pm-8:43 pm

1 stop4h 31m

$261

St. LouisWhite Plains

STL - HPN

STLHPN

Lambert-St Louis

Thu 5/14

6:05 am-11:12 am

1 stop4h 07m

White Plains Westchester County

Sat 5/16

6:22 am-9:40 am

1 stop4h 18m

$345

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 3/28

9:30 am-3:49 pm

1 stop5h 19m

White Plains Westchester County

Tue 4/7

4:29 pm-10:29 pm

1 stop7h 00m

$369

St. LouisWhite Plains

STL - HPN

STLHPN

Lambert-St Louis

Tue 12/30

6:02 am-2:30 pm

1 stop7h 28m

White Plains Westchester County

Fri 1/2

6:27 am-1:36 pm

1 stop8h 09m

$383

St. LouisWhite Plains

STL - HPN

STLHPN

Lambert-St Louis

Wed 12/31

6:00 am-11:29 am

1 stop4h 29m

White Plains Westchester County

Sun 1/4

6:56 pm-11:55 pm

1 stop5h 59m

$388

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 4/1

5:40 am-12:03 pm

1 stop5h 23m

White Plains Westchester County

Mon 4/6

12:23 pm-6:42 pm

1 stop7h 19m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 3/31

7:05 am-2:29 pm

1 stop6h 24m

White Plains Westchester County

Mon 4/6

5:17 pm-8:24 pm

1 stop4h 07m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 4/2

9:43 am-6:19 pm

1 stop7h 36m

White Plains Westchester County

Sat 4/4

12:23 pm-4:28 pm

1 stop5h 05m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 3/31

11:15 am-6:19 pm

1 stop6h 04m

White Plains Westchester County

Sun 4/5

12:23 pm-4:43 pm

1 stop5h 20m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County from Illinois 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 Illinois to Westchester County

What is the cheapest month to book a flight from Illinois to Westchester County?

Currently, August is the cheapest month in which you can book a flight from Illinois to Westchester County (average of $226). Flying from Illinois 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 IL to REU?

Find hourly flight availability from Illinois 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 18, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 27% on flights from Illinois to Westchester County by exploring options for tickets in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Illinois to Westchester County. Price data was last updated on December 16, 2024.

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

Related info for your journey

Find useful and relevant information for your journey from Illinois 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 Illinois to Westchester County?

    Airlines like Delta and American Airlines fly from Illinois to Westchester County in about 4h 07m. The time it takes to get you to your destination can typically vary by up to 14m. The distance from Illinois to Westchester County is about 895 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Illinois to Westchester County that include hotel bookings?

    Yes. In addition to deals on Illinois to Westchester County flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Westchester County?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Westchester County.

  • Can I find deals for business class flights from Illinois to Westchester County?

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to Westchester County?

    Currently, August is the cheapest month in which you can book a flight from Illinois to Westchester County (average of $226). Flying from Illinois 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.

See more FAQs

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Top airline flying from Illinois to Westchester County

Discover the top airline that operate flights from Illinois 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$308Average$572FlexibilityNo cancel feeOn-time71%

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