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$169+ Cheap flights from Westchester County to Chicago (CHI)

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Westchester County to Chicago

Keep the following information in mind while searching for Westchester County to Chicago flight deals. Data was last updated August 14, 2025.

Round-trip from

$349
(American Airlines)

One-way from

$200
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$269
From Westchester County to Chicago (CHI)
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One-way flight from Westchester County to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($32 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 August 2025
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Find flight deals from Westchester County to Chicago

Cheapest flights from Westchester County to Chicago
Explore the most affordable flight options available from Westchester County to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/14. 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 10/14:30 pmHPN - ORD
Nonstop2h 35mAmerican Airlines
Wed 10/298:17 amORD - HPN
Nonstop2h 12mAmerican Airlines
Deal found 8/14$349
This KAYAK deal was found by Cheapflights users on 8/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:30 amHPN - ORD
2 stops10h 28mAmerican Airlines
Mon 10/138:50 pmORD - HPN
2 stops12h 44mAmerican Airlines
Deal found 8/13$350
This Delta deal was found by Cheapflights users on 8/13. 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.
Thu 9/185:20 pmHPN - ORD
1 stop15h 45mDelta
Tue 9/237:10 amORD - HPN
1 stop7h 39mDelta
Deal found 8/13$367
This Delta deal was found by Cheapflights users on 8/14. 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 9/136:00 amHPN - MDW
1 stop4h 47mDelta
Tue 9/166:00 amMDW - HPN
1 stop7h 29mDelta
Deal found 8/14$369
This Delta deal was found by Cheapflights users on 8/14. 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 10/112:42 pmHPN - ORD
1 stop4h 38mDelta
Wed 10/297:10 amORD - HPN
1 stop3h 49mDelta
Deal found 8/14$369
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Sat 10/254:30 pmHPN - ORD
Nonstop2h 41mAmerican Airlines
Mon 10/276:29 pmORD - HPN
Nonstop2h 30mAmerican Airlines
Deal found 8/13$380
This Delta deal was found by Cheapflights users on 8/12. 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.
Thu 9/113:25 pmHPN - ORD
1 stop26h 39mDelta
Sat 9/133:58 pmORD - HPN
1 stop23h 37mDelta
Deal found 8/12$382
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/912:00 pmHPN - ORD
Nonstop2h 36mAmerican Airlines
Sat 9/138:15 amORD - HPN
Nonstop2h 14mAmerican Airlines
Deal found 8/11$384
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 9/2012:42 pmHPN - ORD
1 stop9h 52mDelta
Mon 9/229:10 amORD - HPN
2 stops12h 08mDelta
Deal found 8/13$387
This KAYAK deal was found by Cheapflights users on 8/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:30 amHPN - ORD
2 stops12h 40mAmerican Airlines
Wed 9/108:54 pmORD - HPN
2 stops12h 36mAmerican Airlines
Deal found 8/13$388
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Sat 9/206:30 amHPN - ORD
2 stops13h 06mAmerican Airlines
Tue 9/2312:24 pmORD - HPN
2 stops10h 02mAmerican Airlines
Deal found 8/13$389
This Delta deal was found by Cheapflights users on 8/14. 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 10/2512:55 pmHPN - MDW
1 stop6h 30mDelta
Mon 10/276:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 8/14$400

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Chicago 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 14, 2025.
Use the filters below to find and compare flights from Westchester County to Chicago that are best for you.

Fly from

Westchester County

Fly to

Chicago

Route

Depart

Return

Price

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 9/24

6:00 am-7:30 am

Nonstop2h 30m

Chicago O'Hare Intl

Wed 10/1

7:37 pm-10:59 pm

Nonstop2h 22m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 9/27

6:00 am-7:30 am

Nonstop2h 30m

Chicago O'Hare Intl

Wed 10/1

8:15 am-11:29 am

Nonstop2h 14m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 9/17

6:00 am-7:30 am

Nonstop2h 30m

Chicago O'Hare Intl

Sat 9/20

7:37 pm-10:59 pm

Nonstop2h 22m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 8/30

6:00 am-7:36 am

Nonstop2h 36m

Chicago O'Hare Intl

Sun 8/31

8:17 am-11:28 am

Nonstop2h 11m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 9/13

12:00 pm-1:36 pm

Nonstop2h 36m

Chicago O'Hare Intl

Tue 9/16

12:49 pm-3:59 pm

Nonstop2h 10m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 10/1

12:00 pm-1:36 pm

Nonstop2h 36m

Chicago O'Hare Intl

Wed 10/29

8:17 am-11:29 am

Nonstop2h 12m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 9/16

4:30 pm-6:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

Wed 9/24

12:49 pm-3:59 pm

Nonstop2h 10m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 10/11

6:30 am-3:58 pm

2 stops10h 28m

Chicago O'Hare Intl

Mon 10/13

8:50 pm-10:34 am

2 stops12h 44m

$350

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 9/13

6:00 am-9:47 am

1 stop4h 47m

Chicago Midway

Tue 9/16

6:00 am-2:29 pm

1 stop7h 29m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 9/27

4:29 pm-9:10 pm

1 stop5h 41m

Chicago Midway

Wed 10/1

6:00 am-11:59 am

1 stop4h 59m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 37 results
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Best time to book a flight from Westchester County to Chicago

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

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

Currently, August is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $245). Flying from Westchester County to Chicago in March is currently the most expensive (average of $321). 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 REU to CHI?

Find hourly flight availability from Westchester County to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

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

Weekly flight availability from Westchester County to Chicago

Explore weekly flight availability from Westchester County to Chicago. 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 14, 2025.

The most flights from zzREU to CHI 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).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 14, 2025.
See what other customers who have flown with Delta and American Airlines from Westchester County to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most reliable airlines from Westchester County to Chicago?

    Consider Alaska Airlines (76%), American Airlines (75%) or Envoy Air (75%) when booking your flight. These represent the most reliable airlines when flying from Westchester County to Chicago.

  • What are the cheapest flights from Westchester County to Chicago?

    Looking for the cheapest flight from Westchester County to Chicago? While on average our users pay $587, our data indicates the cheapest price to be $148. The most popular route (White Plains Westchester County - Chicago O'Hare Intl), is priced around $283.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $245). Flying from Westchester County to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Westchester County to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Westchester County to Chicago

Discover the top 2 airlines that operate flights from Westchester County to Chicago. 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$96Average$421FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$334Average$459FlexibilityNo cancel feeOn-time71%

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