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Westchester County

$159+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — HPN
Aug 9 — Aug 161
Sat 8/9
Sat 8/16
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 August 4, 2025.

Round-trip from

$261
(Delta)

One-way from

$159
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$192
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. 4% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 4, 2025.

This Delta deal was found by Cheapflights users on 8/2. 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 stop4h 59mDelta
Sat 11/86:00 amHPN - STL
1 stop7h 35mDelta
Deal found 8/2$261
This Delta deal was found by Cheapflights users on 8/3. 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.
Tue 9/97:15 amORD - HPN
1 stop7h 34mDelta
Tue 9/165:20 pmHPN - ORD
1 stop15h 45mDelta
Deal found 8/3$297
This American Airlines deal was found by Cheapflights users on 8/3. 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 10/18:17 amSTL - HPN
1 stop7h 42mAmerican Airlines
Sat 10/46:00 amHPN - STL
1 stop4h 26mAmerican Airlines
Deal found 8/3$331
This Delta deal was found by Cheapflights users on 8/3. 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.
Tue 9/23:47 pmBMI - HPN
1 stop5h 36mDelta
Tue 9/94:29 pmHPN - BMI
1 stop6h 47mDelta
Deal found 8/3$339
This American Airlines deal was found by Cheapflights users on 8/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2212:49 pmORD - HPN
Nonstop2h 10mAmerican Airlines
Sat 10/254:30 pmHPN - ORD
Nonstop2h 41mAmerican Airlines
Deal found 8/2$349
This Delta deal was found by Cheapflights users on 8/3. 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 9/106:00 amMDW - HPN
1 stop5h 00mDelta
Tue 9/1612:42 pmHPN - MDW
1 stop6h 53mDelta
Deal found 8/3$369
This Delta deal was found by Cheapflights users on 8/2. 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.
Wed 10/156:00 amMLI - HPN
1 stop4h 59mDelta
Sat 10/184:29 pmHPN - MLI
1 stop6h 51mDelta
Deal found 8/2$374
This Delta deal was found by Cheapflights users on 8/3. 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 9/46:10 amEVV - HPN
1 stop4h 50mDelta
Sun 9/76:00 amHPN - EVV
1 stop4h 33mDelta
Deal found 8/3$387
This American Airlines deal was found by Cheapflights users on 8/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/174:19 pmCMI - HPN
1 stop5h 33mAmerican Airlines
Sat 10/187:20 amHPN - CMI
1 stop4h 23mAmerican Airlines
Deal found 8/2$388
This American Airlines deal was found by Cheapflights users on 8/3. 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.
Sun 10/126:00 amMLI - HPN
1 stop4h 29mAmerican Airlines
Sat 10/256:00 amHPN - MLI
1 stop5h 59mAmerican Airlines
Deal found 8/3$397
This American Airlines deal was found by Cheapflights users on 8/3. 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.
Mon 8/186:00 amPIA - HPN
1 stop4h 28mAmerican Airlines
Fri 8/226:00 amHPN - PIA
1 stop4h 37mAmerican Airlines
Deal found 8/3$497
This American Airlines deal was found by Cheapflights users on 8/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:41 amEVV - HPN
2 stops15h 45mAmerican Airlines
Sun 9/76:30 amHPN - EVV
2 stops12h 04mAmerican Airlines
Deal found 8/2$710

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 August 4, 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

St. LouisWhite Plains

STL - HPN

STLHPN

Lambert-St Louis

Tue 11/4

6:00 am-11:59 am

1 stop4h 59m

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

Tue 9/9

7:15 am-3:49 pm

1 stop7h 34m

White Plains Westchester County

Tue 9/16

5:20 pm-8:05 am

1 stop15h 45m

$297

St. LouisWhite Plains

STL - HPN

STLHPN

Lambert-St Louis

Wed 10/1

8:17 am-4:59 pm

1 stop7h 42m

White Plains Westchester County

Sat 10/4

6:00 am-9:26 am

1 stop4h 26m

$331

BloomingtonWhite Plains

BMI - HPN

BMIHPN

Bloomington-Normal

Tue 9/2

3:47 pm-10:23 pm

1 stop5h 36m

White Plains Westchester County

Tue 9/9

4:29 pm-10:16 pm

1 stop6h 47m

$339

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Wed 10/22

12:49 pm-3:59 pm

Nonstop2h 10m

White Plains Westchester County

Sat 10/25

4:30 pm-6:11 pm

Nonstop2h 41m

$349

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 9/10

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Tue 9/16

12:42 pm-6:35 pm

1 stop6h 53m

$369

MolineWhite Plains

MLI - HPN

MLIHPN

Moline Quad-City

Wed 10/15

6:00 am-11:59 am

1 stop4h 59m

White Plains Westchester County

Sat 10/18

4:29 pm-10:20 pm

1 stop6h 51m

$374

EvansvilleWhite Plains

EVV - HPN

EVVHPN

Evansville Dress Regional

Thu 9/4

6:10 am-12:00 pm

1 stop4h 50m

White Plains Westchester County

Sun 9/7

6:00 am-9:33 am

1 stop4h 33m

$387

ChampaignWhite Plains

CMI - HPN

CMIHPN

Champaign University-Willard

Fri 10/17

4:19 pm-10:52 pm

1 stop5h 33m

White Plains Westchester County

Sat 10/18

7:20 am-10:43 am

1 stop4h 23m

$388

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

6:00 am-10:59 am

1 stop5h 59m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/2

Showing 1-10 of 21 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 $339). 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 August 4, 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 August 4, 2025.

The most flights from USIL to zzREU are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 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 August 4, 2025.
Peruse reviews from past customers who have flown with Delta and American Airlines from Illinois to Westchester County to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,986 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
Delta
8.0
Very good
7,986 reviews
Delta
8.0
Very good
7,986 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,986 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Lucy,Nov 2023

ATL - JFK

On time flights; courteous staff; efficient boarding system! Thank you!

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.

  • 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 $339). 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 August 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$308Average$477FlexibilityNo cancel feeOn-time71%

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