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Westchester County

$84+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HPN
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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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 November 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Wed 12/31:03 pmORD - HPN
2 stops22h 36mMultiple Airlines
Wed 12/101:14 pmHPN - ORD
1 stop24h 54mMultiple Airlines
Deal found 11/3$197
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 12/13:43 pmORD - HPN
2 stops27h 47mMultiple Airlines
Fri 12/512:10 pmHPN - ORD
1 stop9h 32mMultiple Airlines
Deal found 11/3$332
This Delta deal was found by Cheapflights users on 11/2. 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 11/46:00 amSTL - HPN
1 stop5h 00mDelta
Sat 11/812:55 pmHPN - STL
1 stop4h 37mDelta
Deal found 11/2$345
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Wed 12/38:16 amORD - HPN
Nonstop2h 13mAmerican Airlines
Wed 12/1012:00 pmHPN - ORD
Nonstop2h 43mAmerican Airlines
Deal found 11/3$349
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Wed 11/194:45 pmCMI - HPN
1 stop5h 44mAmerican Airlines
Sun 11/235:59 pmHPN - CMI
1 stop4h 31mAmerican Airlines
Deal found 11/3$358
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/38:50 amORD - HPN
1 stop6h 47mDelta
Wed 12/1012:45 pmHPN - ORD
1 stop6h 55mDelta
Deal found 11/3$369
This American Airlines deal was found by Cheapflights users on 11/3. 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 12/201:12 pmORD - HPN
1 stop6h 15mAmerican Airlines
Mon 12/296:27 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Deal found 11/3$390
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 11/272:10 pmORD - HPN
Nonstop2h 19mAmerican Airlines
Tue 12/24:30 pmHPN - ORD
Nonstop2h 52mAmerican Airlines
Deal found 11/3$399
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:40 amSTL - HPN
1 stop4h 19mDelta
Sun 11/236:00 amHPN - STL
1 stop5h 43mDelta
Deal found 11/3$399
This Delta deal was found by Cheapflights users on 11/2. 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 12/138:50 amORD - HPN
1 stop6h 47mDelta
Mon 12/155:17 pmHPN - ORD
1 stop4h 18mDelta
Deal found 11/2$400
This Delta deal was found by Cheapflights users on 11/2. 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 12/139:59 amMDW - HPN
1 stop5h 38mDelta
Mon 12/156:10 amHPN - MDW
1 stop6h 45mDelta
Deal found 11/2$400
This Delta deal was found by Cheapflights users on 11/2. 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 12/255:30 amORD - HPN
1 stop5h 30mDelta
Wed 12/3112:55 pmHPN - ORD
1 stop8h 41mDelta
Deal found 11/2$407

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 November 3, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$197
(Kiwi.com)

One-way from

$84
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$209
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 Illinois to Westchester County
Search Deals
One-way flight from Illinois to Westchester County
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High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 3, 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

MolineWhite Plains

MLI - HPN

MLIHPN

Moline Quad-City

Wed 4/15

5:55 am-12:14 pm

1 stop5h 19m

White Plains Westchester County

Sat 4/18

4:19 pm-10:31 pm

1 stop7h 12m

$292

St. LouisWhite Plains

STL - HPN

STLHPN

Lambert-St Louis

Fri 1/2

6:02 am-2:30 pm

1 stop7h 28m

White Plains Westchester County

Sun 1/4

5:16 pm-9:45 pm

1 stop5h 29m

$313

EvansvilleWhite Plains

EVV - HPN

EVVHPN

Evansville Dress Regional

Wed 4/15

6:00 am-12:14 pm

1 stop5h 14m

White Plains Westchester County

Sat 4/18

12:59 pm-4:56 pm

1 stop4h 57m

$339

BloomingtonWhite Plains

BMI - HPN

BMIHPN

Bloomington-Normal

Tue 4/21

6:01 am-12:14 pm

1 stop5h 13m

White Plains Westchester County

Sat 4/25

4:19 pm-10:23 pm

1 stop7h 04m

$339

ChampaignWhite Plains

CMI - HPN

CMIHPN

Champaign University-Willard

Thu 11/20

6:00 am-11:29 am

1 stop4h 29m

White Plains Westchester County

Sun 11/23

4:30 pm-9:30 pm

1 stop6h 00m

$358

ChampaignWhite Plains

CMI - HPN

CMIHPN

Champaign University-Willard

Wed 11/19

4:45 pm-11:29 pm

1 stop5h 44m

White Plains Westchester County

Sun 11/23

5:59 pm-9:30 pm

1 stop4h 31m

$358

SpringfieldWhite Plains

SPI - HPN

SPIHPN

Springfield Capital

Wed 4/1

6:00 am-11:07 am

1 stop4h 07m

White Plains Westchester County

Sat 4/4

4:26 pm-11:04 pm

1 stop7h 38m

$371

St. LouisWhite Plains

STL - HPN

STLHPN

Lambert-St Louis

Thu 11/20

6:40 am-11:59 am

1 stop4h 19m

White Plains Westchester County

Sun 11/23

6:00 am-10:43 am

1 stop5h 43m

$399

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 3/21

7:00 am-11:50 am

1 stop3h 50m

White Plains Westchester County

Tue 3/24

3:15 pm-7:56 pm

1 stop5h 41m

$400

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 12/13

12:59 pm-6:17 pm

1 stop4h 18m

White Plains Westchester County

Sun 12/14

11:23 am-2:44 pm

1 stop4h 21m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 52 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, November is the cheapest month in which you can book a flight from Illinois to Westchester County (average of $209). Flying from Illinois 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 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 November 3, 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.

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 November 3, 2025.

The most flights from USIL 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).

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 5h 19m. The time it takes to get you to your destination can typically vary by up to 2h 09m. 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, November is the cheapest month in which you can book a flight from Illinois to Westchester County (average of $209). Flying from Illinois 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 Illinois 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 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$374Average$465FlexibilityNo cancel feeOn-time71%

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