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Westchester County

$118+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HPN
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
1 adult, Economy
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Cheap 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 September 19, 2025.

Round-trip from

$257
(Delta)

One-way from

$118
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$187
From Illinois to Westchester County
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One-way flight from Illinois to Westchester County
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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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 September 2025
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Find 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 September 19, 2025.

This Delta deal was found by Cheapflights users on 9/18. 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 11/178:50 amORD - HPN
1 stop6h 44mDelta
Thu 11/2712:55 pmHPN - ORD
1 stop4h 41mDelta
Deal found 9/18$257
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/48:53 amSTL - HPN
1 stop6h 45mDelta
Sat 11/86:00 amHPN - STL
1 stop7h 35mDelta
Deal found 9/16$261
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/112:47 pmORD - HPN
2 stops20h 47mMultiple Airlines
Mon 11/1712:10 pmHPN - ORD
1 stop12h 18mMultiple Airlines
Deal found 9/16$268
This Delta deal was found by Cheapflights users on 9/18. 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 11/77:10 amORD - HPN
1 stop3h 49mDelta
Sun 11/96:41 pmHPN - ORD
1 stop6h 20mDelta
Deal found 9/18$277
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Thu 10/211:36 amORD - HPN
1 stop22h 52mMultiple Airlines
Mon 10/68:25 amHPN - ORD
2 stops34h 28mMultiple Airlines
Deal found 9/17$294
This Delta deal was found by Cheapflights users on 9/18. 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 11/198:55 amORD - HPN
2 stops12h 14mDelta
Tue 11/253:08 pmHPN - ORD
1 stop7h 28mDelta
Deal found 9/18$300
This Delta deal was found by Cheapflights users on 9/17. 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 10/306:00 amSTL - HPN
1 stop5h 00mDelta
Sun 11/25:00 amHPN - STL
1 stop5h 31mDelta
Deal found 9/17$307
This American Airlines deal was found by Cheapflights users on 9/18. 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.
Sun 10/126:00 amMLI - HPN
1 stop4h 29mAmerican Airlines
Sat 10/256:59 pmHPN - MLI
1 stop5h 56mAmerican Airlines
Deal found 9/18$307
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 10/911:22 amMLI - HPN
1 stop5h 05mAmerican Airlines
Sun 10/126:00 amHPN - MLI
1 stop5h 52mAmerican Airlines
Deal found 9/17$308
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Thu 10/232:41 pmORD - HPN
1 stop19h 47mMultiple Airlines
Mon 10/271:20 pmHPN - ORD
2 stops31h 43mMultiple Airlines
Deal found 9/17$311
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/162:41 pmORD - HPN
1 stop19h 47mMultiple Airlines
Mon 10/208:25 amHPN - ORD
2 stops33h 48mMultiple Airlines
Deal found 9/18$312
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Fri 11/71:50 pmORD - HPN
2 stops20h 23mMultiple Airlines
Mon 11/1012:10 pmHPN - ORD
1 stop12h 18mMultiple Airlines
Deal found 9/18$325

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 September 19, 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

Thu 11/20

5:32 am-11:59 am

1 stop5h 27m

White Plains Westchester County

Tue 11/25

3:08 pm-9:36 pm

1 stop7h 28m

$257

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Mon 11/17

6:45 am-2:28 pm

1 stop6h 43m

White Plains Westchester County

Tue 11/25

3:08 pm-9:36 pm

1 stop7h 28m

$257

St. LouisWhite Plains

STL - HPN

STLHPN

Lambert-St Louis

Tue 11/4

8:53 am-4:38 pm

1 stop6h 45m

White Plains Westchester County

Sat 11/8

6:00 am-12:35 pm

1 stop7h 35m

$261

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 10/22

11:23 am-6:00 pm

1 stop5h 37m

White Plains Westchester County

Sat 10/25

5:20 pm-8:23 pm

1 stop4h 03m

$277

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 10/16

7:10 am-11:59 am

1 stop3h 49m

White Plains Westchester County

Mon 10/20

4:29 pm-9:24 pm

1 stop5h 55m

$277

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Fri 11/7

7:10 am-11:59 am

1 stop3h 49m

White Plains Westchester County

Mon 11/10

5:14 pm-8:29 pm

1 stop4h 15m

$277

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 12/16

5:32 am-11:59 am

1 stop5h 27m

White Plains Westchester County

Sat 1/17

6:00 am-1:23 pm

1 stop8h 23m

$277

MolineWhite Plains

MLI - HPN

MLIHPN

Moline Quad-City

Sun 10/12

6:00 am-11:29 am

1 stop4h 29m

White Plains Westchester County

Sat 10/25

6:59 pm-11:55 pm

1 stop5h 56m

$307

St. LouisWhite Plains

STL - HPN

STLHPN

Lambert-St Louis

Thu 10/30

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Sun 11/2

5:00 am-9:31 am

1 stop5h 31m

$307

MolineWhite Plains

MLI - HPN

MLIHPN

Moline Quad-City

Thu 10/9

11:22 am-5:27 pm

1 stop5h 05m

White Plains Westchester County

Sun 10/12

6:00 am-10:52 am

1 stop5h 52m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

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, January is the cheapest month in which you can book a flight from Illinois to Westchester County (average of $276). Flying from Illinois to Westchester County in March is currently the most expensive (average of $338). 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 September 19, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Westchester County as you normally would.

Weekly flight availability from Illinois to Westchester County

Explore weekly flight availability from Illinois 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 September 19, 2025.

The most flights from USIL to zzREU are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

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 29m. The time it takes to get you to your destination can typically vary by up to 58m. The distance from Illinois to Westchester County is about 871 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, January is the cheapest month in which you can book a flight from Illinois to Westchester County (average of $276). Flying from Illinois to Westchester County in March is currently the most expensive (average of $338). 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 Illinois to Westchester County

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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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$358Average$459FlexibilityNo cancel feeOn-time71%

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